Sodium Carbonate → HCID 58726897, compound

Participants

Reaction Steps

A mixture of N-(3-(4-(N-tert-butylsulfamoyl)benzo[d]isothiazol-3-ylamino)propyl)-4-iodobenzamide (50 mg, 0.09 mmol), 4-methoxyphenylboronic acid (14 mg, 0.09 mmol), tetrabutylammonium bromide (29 mg, 0.09 mmol), sodium carbonate (29 mg, 0.27 mmol) and palladium (II) acetate (1 mg) in water (3 mL) was microwaved at 160° C. for 5 min. The reaction was diluted with methylene chloride and the mixture was washed successively with aqueous sodium bicarbonate and brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification by column chromatography, on silica gel, eluting with 98:2 methylene chloride:methanol yielded N-(3-(4-(N-tert-Butylsulfamoyl)benzo[d]isothiazol-3-ylamino)propyl)-4′-methoxybiphenyl-4-carboxamide (22 mg), as a white solid. 1H NMR (300 MHz, DMSO-d6)-8.53 (t, 1H), 8.32 (d, 1H), 7.98 (d, 1H), 7.88-7.92 (m, 2H), 7.51-7.70 (m, 5H), 7.00 (d, 2H), 3.80 (s, 3H), 3.38-3.51 (m, 4H), 1.93 (t, 2H), 1.10 ppm (s, 9H). MW=553 confirmed by LC-MS, tr=4.18 min (Method B) MH+=554.

Provenance & Evidence