Dimethylformamide → 4-(4-bromo-2,3-difluorophenyl)-N,2-dimethylnicotinamide

온도

45 °C

To a solution of 4-(4-bromo-2,3-difluorophenyl)-2-methylnicotinic acid (700 mg, 2.13 mmol) in dichloromethane (20 mL) at 0° C. was added oxalyl chloride (0.56 mL, 6.40 mmol) drop wise followed by DMF (0.03 mL, 0.43 mmol). The reaction mixture was heated to 45° C. for 4 h. The reaction mixture was evaporated to dryness. The residue was taken in dichloromethane (50 mL) at 0° C. and methylamine hydrochloride (1.56 g, 23.08 mmol) was added to it followed by triethylamine (4.83 mL, 34.6 mmol). The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with water (50 mL) and extracted with dichloromethane (100 mL). The organic layer was separated, dried over Na2SO4 and concentrated under reduced pressure to afford 4-(4-bromo-2,3-difluorophenyl)-N,2-dimethylnicotinamide (600 mg, 1.76 mmol, 76% crude yield) as yellow semi-solid which was carried on without further purification. LC/MS (ESI) m/e 343.0 [(M+2H)+, calcd for C14H13BrF2N2O 343.0]; LC/MS retention time (method C): tR=1.61 min.

1. customThe reaction mixture was evaporated to dryness
2. customwas taken in dichloromethane (50 mL) at 0° C.
3. extractionextracted with dichloromethane (100 mL)
4. customThe organic layer was separated
5. dry with materialdried over Na2SO4
6. concentrationconcentrated under reduced pressure

ORD 기록

ord-54d39c0c0a25411ea1aca55ef58a3424

출처 데이터셋

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08901305B2