Dimethylformamide → 5-bromo-2-chloro-N-cyclopropylbenzamide

Temperature

0 °C

To a toluene solution (1 M) of 5-bromo-2-chlorobenzoic acid (1 eq.) and DMF (1.2 eq.) was added at 0° C. oxalyl chloride (1.2 eq.) dropwise over 1 h. The resulting solution was stirred at 0° C. for 2 h before the volatiles were removed in vacuo. The resulting residue was taken up in dichloromethane (1 M), cooled to 0° C. and added sequentially cyclopropylamine (1.5 eq.) and Hunig's base (2 eq.) dropwise over 1 h. The resulting suspension was stirred at RT for 18 h. The reaction was quenched with 1 N HCl and extracted with dichloromethane. The combined organic extracts were dried over MgSO4, filtered and the filtrate concentrated in vacuo to ˜⅓ in volume. The resulting white suspension was added an equivalent volume of hexanes and the title compound was isolated via vacuum filtration.

1. customwere removed in vacuo
2. temperaturecooled to 0° C.
3. stirringThe resulting suspension was stirred at RT for 18 h
4. customThe reaction was quenched with 1 N HCl
5. extractionextracted with dichloromethane
6. dry with materialThe combined organic extracts were dried over MgSO4
7. filtrationfiltered
8. concentrationthe filtrate concentrated in vacuo
9. additionThe resulting white suspension was added an equivalent volume of hexanes

ORD record

ord-ec6452fdf13347f698dfb0fc19b47127

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08063105B2