2-Bromothioanisole → HCID 69410336, compound

Participants

Reaction Conditions

Reaction Steps

2-Bromothioanisole (300 mg, 1.48 mmol), (R)-2-methylpiperazine (185 mg, 1.85 mmol), Pd2(dba)3 (32 mg, 0.35 mmol), BINAP (41 mg, 0.66 mmol), sodium t-butoxide (200 mg, 2.08 mmol) and anhydrous toluene (3 ml) were combined in a 15 ml round-bottomed flask. The atmosphere in the flask was evacuated and flushed with nitrogen (3×). The mixture was lowered into an oil bath heated to 100° C. After heating for about 1.2 hours, the mixture was cooled, diluted with ethyl acetate (100 ml), filtered through Celite, and concentrated to a crude oil (285 mg). The oil was loaded onto an cation exchange column, and the column was flushed with methanol (100 ml), and then with 2 M ammonia/methanol (100 ml). The basic methanol solution was concentrated to an oil (250 mg). The oil was further purified by flash chromatography using 19:1 dichloromethane: 0.5 M ammonia/methanol as eluent to yield the final product (160 mg, 58%) as an oil. LRMS (ESI+): 223.0 (M+1)

Provenance & Evidence