Sodium Methoxide → HCID 50994578, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 0.080 g (0.21 mmol) of N-[3-bromo-5-(2-chloro-pyridine-4-carbonyl)-phenyl]-methanesulfonamide in 10.0 mL of anhydrous methanol in a pressure tube was added 0.007 g (0.21 mmol) of sodium methoxide. The tube was sealed and the reaction was heated at 80° C. for 18 hours. The methanol was removed under vacuum and water was added to the reaction mixture. The aqueous phase was extracted with ethyl acetate, washed with water and brine and dried over anhydrous sodium sulfate. The solution was filtered and concentrated to give 0.035 g of N-[3-bromo-5-(2-methoxy-pyridine-4-carbonyl)-phenyl]-methanesulfonamide. The Suzuki reaction and removal of the triisopropylsilyl protecting group were carried out as described in Example 35. 1H NMR (400 MHz, CD3COCD3): δ 10.49 (s, 1H), 8.96 (s, 1H), 8.38 (d, J=5.1 Hz, 1H), 8.07 (t, J=1.9 Hz, 1H), 7.90 (t, J=1.6 Hz, 1H), 7.83 (t, J=1.9 Hz, 1H), 7.51 (d, J=7.8 Hz, 1H), 7.45 (t, J=2.8 Hz, 1H), 7.30 (dd, J=5.1, 1.3 Hz, 1H), 7.26-7.18 (m, 2H), 7.10 (s, 1H), 6.75-6.72 (m, 1H), 3.96 (s, 3H), 3.15 (s, 3H).

Provenance & Evidence