Acetonitrile → HCID 18327737, compound

Participants

Reaction Steps

A mixture of 4-bromo-2-aminotoluene (1.55 g, 7.17 mmol), N-methyl-N-(tert-butoxycarbonyl)-4-penten-2-amine (1.71 g, 8.60 mmol ), prepared as previously described, palladium(II) acetate (16 mg, 0.07 mmol), tri-o-tolylphosphine (87 mg, 0.28 mmol), triethylamine (4.5 mL, 32.28 mmol), and acetonitrile (10 mL) was heated in a sealed glass tube at 140° C. for 14 h. The reaction mixture was cooled to ambient temperature, diluted with water (40 mL) and extracted with chloroform (4×75 mL). The combined extracts were dried over sodium sulfate, filtered and concentrated on a rotary evaporator. The crude product was purified by column chromatography on neutral alumina eluting with ethyl acetate-hexane (2:3 to 4:1) to yield 1.57 g (72.3%) of a brown liquid.

Provenance & Evidence