Potassium Fluoride → HCID 69109369, compound

Participants

Reaction Conditions

Reaction Steps

2-(4-Bromophenyl)isothiazolidine 1,1-dioxide (0.56 g, 2.0 mmol), 1-methyl-5-cyano-2-pyrroleboronic acid (0.36 g, 2.4 mmol), KF (0.38 g, 6.6 mmol), and Pd2(dba)3 (48 mg, 0.05 mmol) were added to a 50 mL round bottom flask under nitrogen. The flask was sealed and purged with nitrogen for 5 minutes. THF (5 mL) was added and the mixture was purged with nitrogen. A solution of tri-t-butylphosphine (10% wt in hexanes) (0.3 mL, 0.1 mmol) was added via syringe and the mixture was stirred vigorously at 25° C. for 16 hours. The mixture was diluted with EtOAc, filtered through a plug of silica gel, washed with 200 mL of EtOAc and concentrated to give a crude brown/black semi-solid. Purification via Isco chromatography (the Redisep® column, silica, gradient 5%-100% ethyl acetate in hexane) afforded 5-[4-(1,1-dioxidoisothiazolidin-2-yl)phenyl]-1-methyl-1H-pyrrole-2-carbonitrile as a white solid (54 mg).

Provenance & Evidence