Yield:-

Reaction Conditions:

with oxalyl dichloride;N,N-dimethyl-formamide in dichloromethane at 0 - 20; for 2.25 h;

Steps:

2

Example 2; tert-Butyl 3-(5-chloro-2-fluoro-4-(5-(6-(trifluoromethyl)imidazo[l,2-fl]pyridin-2-yl)-l,2,4- oxadiazol-3-yl)phenyl)propanoate; 2-Chloro-4-bromo-5-fluoro benzamide (19).; To a stirred solution of 17 (20.0 g, 79.0 mmol) in DCM (200 mL) with a catalytic amount of DMF, was added oxalyl chloride (37.5 g, 295 mmol) at 0 ⁰C. After the addition was complete, the reaction mixture was stirred at 0 ⁰C for 15 min, followed by stirring at room temperature for 2 h. The reaction mixture was concentrated in vacuo to afford 18 as a white solid. The acid chloride 18 was dissolved in THF (300 mL) and was added to aq. NH₃ (600 mL) at -5 ⁰C and stirred for 30 min. The resulting reaction mixture was concentrated in vacuo. The precipitated solid was filtered and washed successively with water and hexane to afford 19 (15 g, 81% yield) as a white solid.

References:

WO2010/65760,2010,A1 Location in patent:Page/Page column 108