[H-].[Na+].[NH2:3][C:4]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:5]=1C(NC)=O.ClC(OC1C=CC=CC=1)=[O:17].[CH3:25][N:26]([CH3:29])[CH:27]=[O:28]>>[F:14][C:12]1[CH:13]=[C:4]2[C:5]([C:27](=[O:28])[N:26]([CH3:29])[C:25](=[O:17])[NH:3]2)=[CH:10][CH:11]=1A suspension of sodium hydride (60% in mineral oil, 368 mg, 9.2 mmol) in dimethylformamide (12 mL) was cooled to 0° C. and treated with 2-amino-4-fluoro-N-methylbenzamide [Intermediate 137] (0.67 g, 4.0 mmol). Phenyl chloroformate (0.6 mL, 0.73 g, 4.7 mmol) was added over 40 minutes. After 1 hour a further portion of phenyl chloroformate (0.6 mL, 0.73 g, 4.7 mmol) was added. The reaction was allowed to warm to room temperature and stir for two hours. The reaction was slowly added to 200 mL of ice. The solid was filtered, washed with methanol to obtain the product (395 mg, 51%).
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