Acetic Acid → HCID 9909300, compound

Participants

Reaction Steps

To a solution of 2-bromothiophene (1.0 g, 6.1 mmol) in tetrahydrofuran (50 mL) at -78° C., was added n-butyl lithium (1.6 M in cyclohexane, 4.0 mL) and the resulting solution was stirred for 5 minutes. At this time, ZnCl2 (0.5 M in THF, 20 mL) was added and the solution was warmed to room temperature over 2 hours. To the reaction mixture was then added palladium tetrakis(triphenylphosphine) (200 mg) and a solution of the acetic acid salt of 7-bromo-2-(4-piperonyl-1-piperazinyl)-2,4,6-cycloheptatriene-1-one (300 mg, 0.74 mmol, example 1b) in tetrahydrofuran (5 mL) and the resulting mixture was refluxed for 18 hours. The reaction was quenched with a saturated aqueous ammonium chloride solution and the product, extracted into methylene chloride (3×200 mL). The crude product was purified by silica gel chromatography to provide the title compound as a dark yellow oil (50 mg, 50%).

Provenance & Evidence