Methyl 6-(methylsulfonyl)nicotinate synthesis

Yield:1190948-26-5 88%

Reaction Conditions:

in dimethyl sulfoxide at 100; for 1 h;

Steps:

11.AA Procedure AA: Preparation of methyl 6-(methylsulfonyl)nicotinate

To a stirring solution of methyl 6-chloronicotinate (2.00 g, 11.7 mmol) in DMSO (10 mL), was added sodium methanesulfinate (1.78 g, 17.5 mmol) at rt in one lot. The resulting mixture was heated to 100 °C for 1 h. The reaction mixture was cooled to rt, and then dilute with water (100 mL). The product was then extracted with ethyl acetate (30 mL x 3) and the combined organics were washed with water (20 mL) and brine (20 mL). After drying over Na₂S0₄, the solvent was removed in vacuo to afford methyl 6-(methylsulfonyl)nicotinate (2.20 g, 88%) as an off-white solid. 'H NMR (300 MHz, CDC) δ ppm: 9.31 (dd, J= 2.1, 0.9 Hz, 1H), 8.59 (dd, ./ = 8.1, 2.0 Hz, 1H), 8.20 (dd, J= 8.1, 0.9 Hz, 1H), 4.04 (s, 3H), 3.30 (s, 3H).

References:

WO2017/136871,2017,A1 Location in patent:Paragraph 0237