These common heterocyclic compound, 1943-79-9, name is Phenyl methylcarbamate, 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. 1943-79-9
5-((2-amino-4-pyridyl)oxy)-3-chloro-1H-1-indole (4.0 g, 15 mmol, CAS No. 417721-98-3) which was described in WO 02/32872 was dissolved in N,N-dimethylformamide (20 ml); sodium hydride (0.68 g, 60% in oil) and phenyl N-methylcarbamate (2.6 g, the product of Production example 2-1) were added thereto; and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was partitioned between ethyl acetate and water; and the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Fuji Silysia NH, hexane: ethyl acetate = 1: 2) to yield the title compound as a colorless amorphous solid(1.5 g). 1H-NMR Spectrum (DMSO-d6) delta (ppm): 2.83 (3H, d, J=4.0 Hz), 5.78 (1H, d, J=2.0 Hz), 5.88 (2H, brs), 6.14 (1H, dd, J=2.0, 5.8 Hz), 7.14 (1H, dd, J=2.4, 9.0 Hz), 7.23 (1H, d, J=2.4 Hz), 7.78 (1H, d, J=5.8 Hz), 8.08 (1H, s), 8.19 (1H, m), 8.32 (1H, d, J=9.0 Hz).
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 1943-79-9.
Reference:
Patent; Eisai Co., Ltd.; EP1522540; (2005); A1;,
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