Cesium carbonate → HCID 5330831, compound

Participants

Reaction Steps

A N,N-Dibenzyl-4-iodobenzenesulfonamide Compound 2a (20.4 mg, 0.044 mmol), Pd2(dba)3 (1.0 mg), BINAP (1.8 mg) and cesium carbonate (13 mg, 0.04 mmol) were added to a solution of Compound 1 (10 mg, 0.04 mmol) in dioxane (0.20 mL) and toluene (0.25 mL). The resulting mixture was stirred in an oil-bath (at a temperature of from about 90 to about 100° C.) for about 24 hours. The mixture was cooled to rt then water (20 mL) was added and extracted with methylene chloride (4×20 mL). The organic layers were combined, dried and evaporated, then separated by chromatography (on silica gel, eluting with 1:1 ethyl acetate:hexane) to give a 4-[[6-amino-5-(2,6-difluorobenzoyl)-2-pyridinyl]amino]-N,N-bis(phenylmethyl)benzenesulfonamide Compound 2b (11 mg, 46% yield) as a yellow powder. 1H NMR (300 MHz, CDCl3) δ 9.0 (s, br, 2H), 7.80 (d, 2H), 7.62 (d, 2H), 7.40–7.58 (m, 2H), 7.35–6.95 (m, 12H), 6.40 (s, br, 1H), 6.12 (d, 1H), 7.35 (s, 4H); MS (ESI) m/z: 585 (M+H+), 607 (M+Na+).

Provenance & Evidence