Pyridine → 2-Bromo-N-(3-butyramidophenyl)benzamide

2-Bromobenzoic acid (259 mg, 1.29 mmol) was sealed in a flask with stir bar under nitrogen, then dissolved with dichloromethane (7.5 mL) and cooled on ice. Oxalyl chloride (113 μL, 1.29 mmol) and N,N-dimethylformamide (4 μL, 0.06 mmol) were added, then the reaction was removed from the ice bath and stirred for 3 h with a vent to an oil bubbler. N-(3-Aminophenyl)butyramide (200 mg, 1.12 mmol) was then added, followed by pyridine (209 μL, 2.58 mmol). After 18 h, LC-MS analysis showed complete consumption of the amine reactant. The reaction was diluted with ethyl acetate (40 mL) and 1 M aqueous HCl (40 mL), then the layers were separated and the organic phase was washed again with aqueous HCl, then twice with half-saturated aqueous NaHCO3, then brine. The organics were dried over Na2SO4, filtered, and concentrated to a colorless oil. The oil was redissolved with dichloromethane, then hexane was added to induce the precipitation of an amorphous solid. The suspension was concentrated and dried under hi-vacuum to yield the title compound (382 mg, 94%). LRMS (ESI+) (M+H): 361.12.

1. temperaturecooled on ice
2. customthe reaction was removed from the ice bath
3. stirringstirred for 3 h with a vent to an oil bubbler
4. customconsumption of the amine reactant
5. additionThe reaction was diluted with ethyl acetate (40 mL) and 1 M aqueous HCl (40 mL)
6. customthe layers were separated
7. washthe organic phase was washed again with aqueous HCl
8. dry with materialThe organics were dried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated to a colorless oil
11. dissolutionThe oil was redissolved with dichloromethane
12. additionhexane was added
13. customthe precipitation of an amorphous solid
14. concentrationThe suspension was concentrated
15. customdried under hi-vacuum

ORD record

ord-94db6c20cbce479ebfba7c1ce825a282

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09422262B2