Oxalyl chloride → 4-(4-chloro-2-fluorophenyl)-N,2-dimethylnicotinamide

To a solution of 4-(4-chloro-2-fluorophenyl)-2-methylnicotinic acid (180 mg, 0.678 mmol) in DCM (5 mL) and DMF (0.2 mL) at 0° C., was added oxalyl chloride (0.178 mL, 2.033 mmol). The reaction mixture was stirred for 3 h at RT then diluted with DCM (5 mL) and treated with a solution of methylamine hydrochloride (457 mg, 6.78 mmol) in DCM (5 mL) cooled to 0° C. The mixture was stirred for another 1 h at RT. The solution was extracted with DCM (20 mL), washed with saturated NaHCO3 (2×10 mL) and water (20 mL); dried over Na2SO4 and concentrated under reduced pressure to afford 4-(4-chloro-2-fluorophenyl)-N,2-dimethylnicotinamide (50 mg, 0.179 mmol, 27% yield) as a brown gum. LC/MS, (ESI) m/z 279.2 [(M+H)+, calcd for C14H13ClFN2O 279.1]; LC/MS retention time (method D): tR=0.62 min.

1. temperaturecooled to 0° C
2. stirringThe mixture was stirred for another 1 h at RT
3. extractionThe solution was extracted with DCM (20 mL)
4. washwashed with saturated NaHCO3 (2×10 mL) and water (20 mL)
5. dry with materialdried over Na2SO4
6. concentrationconcentrated under reduced pressure

ORD record

ord-ac5201aebf5c4e909cd4fe699727074c

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08901305B2