Ethanol → HCID 21186252, compound

Participants

Reaction Conditions

Reaction Steps

Tetrakis(triphenylphosphine)palladium (0) (500 mg) was added to a deoxygenated solution of sodium carbonate (3.74 g), 4-(2-carboxypropyl)phenyl boronic acid (3.67 g) and 2-chloro-N-(isobutoxycarbonyl)-N-(3-methoxy-5-methyl-pyrazin-2-yl)pyridine-3-sulphonamide (6.1 g) in a mixture of water (30 ml), ethanol (75 ml) and toluene (75 ml). The mixture was stirred and heated under argon at 80° C. for 17 hours and then allowed to cool to ambient temperature. Ice water (5 g) was added and the reaction extracted with ethyl acetate (75 ml). The combined organic layers were extracted with saturated aqueous sodium carbonate solution (2×15 ml) and combined aqueous extracts were acidified to pH 2 with 2M hydrochloric acid and extracted with ethyl acetate (3×100 ml). The combined organic extracts were dried (MgSO4) and evaporated to low volume affording crystalline material which was filtered and washed with diethyl ether to give N-(isobutoxycarbonyl)-2-(4-(2-carboxypropyl)phenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (3.11 g); NMR 1H (d6-DMSO): 0.61 (d, 6H), 1.09 (d, 3H), 1.50-1.73 (m, 1H), 2.55 (partly obscured by DMSO, 3H), 2.6-2.77 (m, 2H), 2.72-3.09 (m, 1H), 2.83 (d, 2H), 3.96 (s, 3H), 7.25 (d, 2H), 7.43 (d, 2H), 7.78 (dd, 1H), 8.15 (s, 1H), 8.83-8.96 (m, 2H), 12.14 (br s, 1H); mass spectrum (−ve ESP) 541.1 (M−H)−.

Provenance & Evidence