Potassium Fluoride → HCID 68426073, compound

Participants

Reaction Conditions

Reaction Steps

5-Bromoindoline (0.59 g, 3.0 mmol), 1-methyl-5-cyano-2-pyrroleboronic acid (0.54 g, 3.6 mmol), potassium fluoride (KF—0.57 g, 9.9 mmol), and Pd2(dba)3 (72 mg, 0.075 mmol) were added to a round bottom flask under nitrogen. The flask was sealed and purged with nitrogen for 5 minutes. Tetrahydrofuran (THF—7.5 mL) was added and the mixture was purged with nitrogen for an additional 5 minutes. A solution of tri-t-butylphosphine (10% wt in hexanes, 0.45 mL, 0.15 mmol) was added via syringe and the mixture was stirred vigorously at 25° C. for 5 hours. The mixture was diluted with ethyl acetate, filtered through a plug of silica gel, washed through with additional ethyl acetate and concentrated to give a crude brown/black semi-solid. Purification was performed using Isco chromatography (the Redisep® column, silica, gradient 10-60% ethyl acetate in hexane). Further purification via Isco chromatography (the Redisep® column, silica, gradient 50% hexane:45% methylene chloride:5% ethyl acetate) afforded 5-(2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-pyrrole-2-carbonitrile (0.24 g) as a white solid. HPLC purity 100.0% at 210-370 nm, 8.5 min.; the Xterra® column RP18, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammonium formate buffer pH=3.5 acetonitrile+MeOH) for 10 minutes, hold 4 minutes. HRMS: calcd for C14H13N3+H+, 224.11822; found (ESI, [M+H]+), 224.1188;

Provenance & Evidence