Some common heterocyclic compound, 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, molecular formula is C6H3Cl2N3, 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. COA of Formula: C6H3Cl2N3
To a 100 mL flask was added 2,4-dichloropyrrolo[2,l-^[l,2,4]triazine (3 g, 15.96 mmol), tetrahydrofuran (40 mL) and stirred. To the resulting solution was portionwise added sodium phenolate (2.038 g, 17.55 mmol). After 1 h, an aliquot of the reaction mixture was diluted with methanol and anlayzed by LCMS to ensure complete conversion. The reaction mixture was concentrated. To the residue was added water, stirred, filtered and dried. Obtained 2-chloro-4-phenoxypyrrolo[2,l- |[l,2,4]triazine (3.71 g, 15.10 mmol, 95 % yield) as an off-white solid. LCMS: RT = 1.05 min; MS(ES): m/z observed = 245.9, 247.9 (Injection conditions: Column: Waters Acquity UPLC BEH C18, 2.1 x 50 mm, 1.7-muiotaeta particles; Mobile Phase A: 100% water with 0.05% TFA; Mobile Phase B: 100% MeCN with 0.05% TFA; Gradient: 2-98% B over 1 minute, then a 0.5- minute hold at 98% B; Flow: 0.8 mL/min; Detection: UV at 220 nm); NMR (300 MHz, DMSO-de) delta 8.13 (dd, J=2.6, 1.5 Hz, 1H), 7.56 – 7.48 (m, 2H), 7.42 – 7.34 (m, 3H), 7.15 (dd, J=4.5, 1.5 Hz, 1H), 6.99 (dd, J=4.5, 2.6 Hz, 1H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 918538-05-3, its application will become more common.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BORZILLERI, Robert M.; FINK, Brian E.; HARIKRISHNAN, Lalgudi S.; WARRIER, Jayakumar Sankara; (87 pag.)WO2017/40448; (2017); A1;,
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