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Sources of common compounds: 39065-95-7

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-(Chlorodifluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Synthetic Route of 39065-95-7, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 39065-95-7, name is 4-(Chlorodifluoromethoxy)aniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a reaction flask were added 6-chloro-5-bromonicotinic acid (1.17 g, 4.97 mmol), 4-(chlorodifluoromethoxy)aniline (0.8 g, 4.15 mmol), dissolved with 20 mL anhydrous DMF, 2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU, 2.1 g, 5.39 mmol) and N,N-diisopropylethylamine (DIPEA, 534 mg, 4.15 mmol) were added, and the reaction was stirred under nitrogen protection at room temperature for 18 hours. The reaction was diluted with large amount of water, extracted with ethyl acetate for 3-4 times, the organic layers were combined, washed with brine, concentrated, purified by column chromatography, dried in vacuum to afford 1.18 g of a product, yield: 69.5%.

Reference:
Patent; Shenzhen Targetrx, Inc.; WANG, Yihan; ZHAO, Jiuyang; AL, Yixin; (55 pag.)EP3553056; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Continuously updated synthesis method about 39065-95-7

The synthetic route of 39065-95-7 has been constantly updated, and we look forward to future research findings.

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 39065-95-7, name is 4-(Chlorodifluoromethoxy)aniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C7H6ClF2NO

[00542] (R)-6-(3-Hydroxypyrrolidin-l-yl)-5-(pyrimidin-5-yl)nicotinic acid (Stage 170.1, 57.3 mg, 0.2 mmol), HOBT (43.5, 0.284 mmol) and EDC (42.2 mg, 0.22 mmol) were dissolved in 0.3 M NMM in DMF (0.8 niL) at RT. 4-(Chlorodifluoromethoxy)aniline (36.8 mg, 0.19 mmol) was added and the RM was stirred for 5 h. The RM was then diluted with EtOAc and washed with 10% NaHCC>3. The organic layer was dried over Na2S04, filtered and evaporated to dryness under reduced pressure. The residue was purified by flash chromatography (RediSep Silica gel column, DCM / MeOH, from 2 to 5% MeOH) and treated with Si-Thiol (50 mg) in MeOH to afford the title compound. HPLC Chiral (CHIRALPAK AD-H, 250 x 4.6 mm, eluent : EtOH/MeOH (50:50), 0.5 mL/min, UV 210 nm) tR = 21.89 min, UPLC-MS (Condition 3) tR = 0.95 min, m/z = 462.2 / 464.2 [M+H]+; XH-NMR (400 MHz, DMSO-d6) delta ppm 1.67 – 1.78 (m, 1 H) 1.80 – 1.89 (m, 1 H) 2.87 (d, J = 11.34 Hz, 1 H) 3.21 (m, J = 11.10, 4.90 Hz, 2 H) 3.33 – 3.44 (m, 1 H) 4.12 – 4.24 (m, 1 H) 4.87 (d, J = 3.52 Hz, 1 H) 7.33 (d, J = 8.60 Hz, 2 H) 7.77 – 7.89 (m, 2 H) 8.08 (d, J = 2.35 Hz, 1 H) 8.78 (d, J = 2.35 Hz, 1 H) 8.88 (s, 2 H) 9.18 (s, 1 H) 10.17 (s, 1 H).

The synthetic route of 39065-95-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; GROTZFELD, Robert Martin; JONES, Darryl Brynley; MANLEY, Paul; MARZINZIK, Andreas; PELLE, Xavier Francois Andre; SALEM, Bahaa; SCHOEPFER, Joseph; SPIESER, erich Alois; WO2013/171640; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Brief introduction of 39065-95-7

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 39065-95-7.

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 39065-95-7, name is 4-(Chlorodifluoromethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 39065-95-7

To a solution of (R)-7-bromo-2-(difluoromethyl)-1-(1-hydroxypropan-2-yl)-1H-benzo[d]imidazole-5-carboxylic acid (5c, 100 mg, 0.286 mmol, 1 eq) and 4-(chlorodifluoromethoxy)aniline (1h, 66.54 mg, 0.344 mmol, 1.2 eq) in DMF (2 mL) was added HATU (130.69 mg, 0.344 mmol, 1.2 eq) and DIEA (148.08 mg, 1.15 mmol, 199.56 uL, 4 eq). The mixture was stirred at 15 C. for 12 hr. LCMS showed 5c was consumed completely and desired MS was detected. The mixture was diluted with water (5 mL) and extracted with EtOAc (10 mL*3). The combined organic layers were washed with brine (5 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to give the crude residue. The residue was purified by prep-TLC (SiO2, ethyl acetate_methanol=10:1) to afford 5e as a yellow oil. 1H NMR (400 MHz, DMSO-d6) delta 10.56 (s, 1H), 8.49 (s, 1H), 8.21 (s, 1H), 7.93 (d, J=9.3 Hz, 2H), 7.43-7.71 (m, 1H), 7.38 (br d, J=9.0 Hz, 2H), 6.02 (br d, J=6.2 Hz, 1H), 5.23-5.45 (m, 1H), 3.72-3.93 (m, 2H), 1.60 (br d, J=6.8 Hz, 3H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 39065-95-7.

Reference:
Patent; Terns, Inc.; ROMERO, F. Anthony; KIRSCHBERG, Thorsten A.; HALCOMB, Randall; XU, Yingzi; (144 pag.)US2020/87283; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Continuously updated synthesis method about C7H6ClF2NO

Adding a certain compound to certain chemical reactions, such as: 39065-95-7, name is 4-(Chlorodifluoromethoxy)aniline, belongs to chlorides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 39065-95-7, name: 4-(Chlorodifluoromethoxy)aniline

To a solution of 3-isopropyl-4-(pyrimidin-5-yl)-3H-imidazo[4,5-c]pyridine-6-carboxylic acid (27d, 32 mg, 0.113 mmol) and 1h (32.80 mg, 0.169 mmol) in DMF (2 mL) was added DIEA (43.80 mg, 0.339 mmol, 59.03 uL) and HATU (51.54 mg, 0.136 mmol). The mixture was stirred at 25 C. for 4 hr. LCMS showed 27d was consumed completely and desired MS was detected. The mixture was diluted with water (5 mL) and extracted with EtOAc (5 mL*3). The combined organic layers were washed with brine (5 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue. The residue was purified by prep-TLC (SiO2, petroleum ether: ethyl acetate=0:1) to afford 27 as a white solid. MS mass calculated for [M+H]+ (C21H17O2N6ClF2) requires m/z 459.1, LCMS found m/z 459.0. 1H NMR (400 MHz, DMSO-d6) delta 10.61 (s, 1H), 9.42 (s, 1H), 9.30 (s, 2H), 8.94 (s, 1H), 8.50 (s, 1H), 8.05-7.95 (m, 2H), 7.37 (d, J=9.0 Hz, 2H), 4.38-4.09 (m, 1H), 1.38 (d, J=6.7 Hz, 6H).

Some tips on 4-(Chlorodifluoromethoxy)aniline

The synthetic route of 39065-95-7 has been constantly updated, and we look forward to future research findings.

Electric Literature of 39065-95-7, A common heterocyclic compound, 39065-95-7, name is 4-(Chlorodifluoromethoxy)aniline, molecular formula is C7H6ClF2NO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a mixture of 1,2-dimethyl-4-(pyrimidin-5-yl)-1H-benzo[d]imidazole-6-carboxylic acid (4d, 15 mg, 0.056 mmol, 1 eq) and HATU (25.51 mg, 0.067 mmol, 1.2 eq), DIPEA (14.45 mg, 0.112 mmol, 19.48 uL, 2 eq) in DMF (1 mL) at 20 C. was added 4-[chloro(difluoro)methoxy]aniline (1h, 16.24 mg, 0.084 mmol, 1.5 eq). The mixture was stirred at 20 C. for 16 hours. The mixture was concentrated in vacuo. LCMS showed desired MS. The mixture was poured into water and extracted with EtOAc, and the combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give the crude product. The residue was purified by prep-HPLC (TFA condition, column: Nano-Micro UniSil 5-100 C18 ULTRA 100*250 mm 5 um; mobile phase: [water (0.1%TFA)-ACN]; B %: 25%-50%, 11 min) to afford the title compound 4 as a white solid. MS mass calculated for [M+H]+ (C21H16ClF2N5O2) requires m/z 444.1, LCMS found m/z 444.1. 1H NMR (400 MHz, MeOD-d4) delta 9.33-9.25 (m, 3H), 8.48 (s, 1H), 8.25 (s, 1H), 7.88 (d, J=9.0 Hz, 2H), 7.33 (d, J=8.8 Hz, 2H), 4.07 (s, 3H), 2.85 (s, 3H).

The synthetic route of 39065-95-7 has been constantly updated, and we look forward to future research findings.

Share a compound : C7H6ClF2NO

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(Chlorodifluoromethoxy)aniline, its application will become more common.

Related Products of 39065-95-7,Some common heterocyclic compound, 39065-95-7, name is 4-(Chlorodifluoromethoxy)aniline, molecular formula is C7H6ClF2NO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A stirred solution of 6-hydroxy-5-iodonicotinic acid (40 g) and DMF (3.51 mL) in toluene (315 mL) was treated dropwise with SOd2 (43.9 mL) at RT and then stirred at 85C for 2.5 h. The solvent was evaporated off under reduced pressure and the residue was redissolved in DCM (315 mL). The solution was cooled in an icy water bath and to this solution a mixture of 4-(chlorodifluoromethoxy)aniline (26 .3 g) and Et3N (63 mL) in DCM (315 mL) was added dropwise. The mixture was stirred at rt for 1 hr. Then a saturated aqueous solution of NaHCO3 was added and the mixture was stirred at rt for 10 mm and a solid was formed. The mixture was then diluted with 315 mL of hexane and filtered to collect the white solid, washed with more water and air dried to afford 6-chloro-N-(4-(chlorodifluoromethoxy)phenyl)-5-iodonicotinamide (55.97 g). (Rt = 2.28 mi +ESI m/z: MH+ = 459.0).

Reference:
Patent; ASTAR BIOTECH LLC; LI, Lianhai; YU, Chunrong; HUANG, Haihong; (94 pag.)WO2017/186148; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Introduction of a new synthetic route about 39065-95-7

The synthetic route of 39065-95-7 has been constantly updated, and we look forward to future research findings.

Electric Literature of 39065-95-7,Some common heterocyclic compound, 39065-95-7, name is 4-(Chlorodifluoromethoxy)aniline, molecular formula is C7H6ClF2NO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of 7-bromo-1-((1s,3s)-3-hydroxycyclobutyl)-1H-benzo[d]imidazole-5-carboxylic acid (2b, 100 mg, 0.321 mmol, 1 eq) and 4-[chloro(difluoro)methoxy]aniline (74.66 mg, 0.386 mmol, 1.2 eq) in DMF (2 mL) was added HATU (146.65 mg, 0.386 mmol, 1.2 eq) and DIEA (83.08 mg, 0.643 mmol, 111.97 uL, 2 eq). The mixture was stirred at 15 C. for 12 hr. LCMS showed 2b was consumed completely and desired MS was detected. The mixture was diluted with water (3 mL) and extracted with EtOAc (10 mL¡Á3). The combined organic layers were washed with brine (3 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue. The residue was purified by prep-TLC (SiO2, ethyl acetate_methanol=10:1) to give 2c as a white solid. 1H NMR (400 MHz, DMSO-d6) delta10.48 (s, 1H) 8.72 (s, 1H) 8.40 (d, J=1.3 Hz, 1H) 8.05 (d, J=1.3 Hz, 1H) 7.92 (d, J=9.0 Hz, 2H) 7.36 (d, J=9.0 Hz, 2H) 5.37 (d, J=6.4 Hz, 1H) 4.96-5.08 (m, 1H) 4.01-4.13 (m, 1H) 2.89-2.98 (m, 2H) 2.36-2.43 (m, 2H).

The synthetic route of 39065-95-7 has been constantly updated, and we look forward to future research findings.

Continuously updated synthesis method about 39065-95-7

The synthetic route of 39065-95-7 has been constantly updated, and we look forward to future research findings.

Reference of 39065-95-7, A common heterocyclic compound, 39065-95-7, name is 4-(Chlorodifluoromethoxy)aniline, molecular formula is C7H6ClF2NO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a mixture of 3-bromo-4-(methylamino)-5-nitrobenzoic acid (6a, 1.27 g, 6.54 mmol, 1.2 eq) and 4-(chlorodifluoromethoxy)aniline (1h, 1.50 g, 5.45 mmol, 1 eq) in DMF (10 mL) was added HATU (2.28 g, 6.00 mmol, 1.1 eq) and DIEA (775.28 mg, 6.00 mmol, 1.04 mL, 1.1 eq) in one portion. The mixture was heated to 30 C. and stirred for 12 hours. LC-MS showed one main peak with desired mass was detected. The mixture was concentrated and the resulting residue was purified by column chromatography (SiO2, petroleum ether:ethyl acetate=20:1 to 5:1) to yield 6b as a yellow solid.

The synthetic route of 39065-95-7 has been constantly updated, and we look forward to future research findings.

Simple exploration of 39065-95-7

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 39065-95-7.

[00713] 6-Chloro-5-iodo-3-pyridinecarboxylic acid (18 g, 62.2 mmol) was suspended in toluene (125 mL). DMF (1.446 mL, 18.67 mmol) and SOCl2 (13.63 mL, 187 mmol) were added at RT. The RM was stirred at 80C for 1 h, cooled to RT then the solvent was evaporated off under reduced pressure to give a residue that was dissolved in THF (125 mL) and cooled to – 15C. DIPEA (21.74 mL, 124 mmol) was added at -15C, and the cold mixture was treated dropwise with a solution of 4-(chlorodifluoromethoxy)aniline in THF (125 mL) over 12 min. The resulting fine orange suspension was stirred for 1 h at RT. The solvent was evaporated off under reduced pressure and the residue was dissolved in TBME (500 mL),and sequentially washed with IN HC1 (2 x 150 mL), sat. aq. NaHC03 solution (2 x 150 mL) and brine (2 x 150 mL). The aq. phases were extracted with TBME (400 mL). Combined organic phases were dried over Na2S04, filtered and concentrated under reduced pressure until crystallization began (around 100 mL). n- Heptane (800 mL) was then added with stirring and the light yellow suspension was stirred at RT for 30 min. The crystalline product was filtrated , washed with n-heptane (200 mL) and dried to afford the title product as a beige solid. LC-MS (Condition 3) tR 1.25 min, 459.0/460.7/462.1

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 39065-95-7.