Potassium Carbonate → N-(4-(benzyloxy)pyridin-3-yl)-N-(methylsulfonyl)methane sulfonamide

Temperature

0 °C

4-(Benzyloxy)-3-nitropyridine (14 g, 69.8 mmol, 1 eq) was dissolved in dichloromethane and cooled to 0° C. Then added TEA (29.2 ml, 209.6 mmol, 3 eq), followed by the addition of potassium carbonate (9.96 g, 69.8 mmol, 1 eq) at 0° C. and stirred for 15 minutes. Methane sulfonyl chloride (20 g, 174 mmol, 2.5 eq) was added slowly at 0° C. to the above mixture and stirred for 14 h. After the completion of reaction, monitored by TLC, the reaction mixture was diluted with water and organic layer was separated. Water layer was extracted twice with 200 ml of dichloromethane, and the combined dichloromethane mixture was washed with water (500 ml) and brine (500 ml). The organic solution was concentrated under vacuum to yield the pure product. Yield: 19.5 g (78%). 1HNMR (400 MHz, DMSO-d6): δ 3.47 (S, 6H), 5.35 (s, 2H), 7.32 (d, J=5.76 Hz, 1H), 7.40-7.49 (m, 3H), 7.51 (t, J=4.12 Hz, 2H), 8.52 (d, J=5.68 Hz, 1H), 8.57 (s, 1H).

1. stirringstirred for 14 h
2. customAfter the completion of reaction
3. customwas separated
4. extractionWater layer was extracted twice with 200 ml of dichloromethane
5. washthe combined dichloromethane mixture was washed with water (500 ml) and brine (500 ml)
6. concentrationThe organic solution was concentrated under vacuum
7. customto yield the pure product

ORD record

ord-7882a6887c8148c58304cfc3d501c226

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08536338B2