Tris(1,1-dimethylethyl)phosphine → HCID 25005618, compound

Participants

Reaction Steps

According to general procedure B, 4-bromo-N,N-diethyl-3-fluorobenzenesulfonamide (183 mg, 0.59 mmol), 5-cyano-1-methyl-1H-pyrrol-2-ylboronic acid (106 mg, 0.70 mmol), potassium fluoride (113 mg, 1.95 mmol), and tris(dibenzylideneacetone)dipalladium (0) (15 mg, 0.01 mmol) were placed in an oven dried flask under nitrogen and dry THF (1.4 mL) was added. Tri-t-butylphosphine (89 μL, 0.02 mmol, 10 wt % in hexane) was added and the reaction was stirred for 16 hours. 4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-N,N-diethyl-3-fluorobenzenesulfonamide (46 mg, 23%) was provided after purification. HRMS: calcd for C16H18FN3O2S+H+, 336.11765; found (ESI, [M+H]+), 336.117. HPLC purity 99.7% at 210-370 nm, 9.7 min.; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min., 85/15-5/95 (ammonium formate buffer pH=3.5/ACN+MeOH) for 10 min., hold 4 min.

Provenance & Evidence