Triethylamine → N-(5-bromopyridin-3-yl)cyclopropanesulfonamide

Cyclopropanesulfonyl chloride was added dropwise to a solution of 5-Bromo-pyridin-3-ylamine (346 mg, 2 mmol), 4-dimethylaminopyridine (25 mg, 0.205 mmol) and triethylamine (0.558 mL, 4 mmol) in dichloromethane (4 mL) at room temperature under nitrogen. The reaction was stirred at this temperature for 15 h. The reaction mixture was diluted with ethyl acetate (50 mL) and the resulting solution was washed with saturated NaHCO3 solution (25 mL). The aqueous phase was extracted with ethyl acetate (50 mL). The combined organic phase was dried over anhydrous Na2SO4. After filtration and concentration, the residue was purified by flash column (0-10% CH3OH in CH2Cl2 v/v) and 248 mg of the desired product as a white solid was obtained. ESI-MS m/z: 278.9 [M+1]+, Retention time 1.02 min; 1HNMR (MeOD, 400.342 MHz) δ 1.00-1.10 (m, 4H), 2.63-2.69 (m, 1H), 3.31 (s, 1H), 7.94 (t, J=2 Hz, 1H), 8.39 (s, 1H), 8.40 (d, J=2 Hz, 1H).

1. washthe resulting solution was washed with saturated NaHCO3 solution (25 mL)
2. extractionThe aqueous phase was extracted with ethyl acetate (50 mL)
3. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
4. filtrationAfter filtration and concentration
5. customthe residue was purified by flash column (0-10% CH3OH in CH2Cl2 v/v) and 248 mg of the desired product as a white solid
6. customwas obtained

ORD record

ord-6e35eb5c7419467e9d03b41008ee630f

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08455522B2