Triethylamine → N-(2-Fluoro-5-trimethylsilanylethynylbenzyl)-acetamide

Participants

Reaction Conditions

Reaction Steps

Combine N-(5-bromo-2-fluorobenzyl)acetamide, (prepared as described in PREPARATION 30), (370 mg, 1.50 mmol, zinc(II) bromide (588 mg, 2.25 mmol), and triethylamine (1.00 mL, 7.20 mmol) in tetrahydrofuran (3.7 mL). After stirring for 5 min, add trimethylsilylacetylene (0.53 mL, 3.76 mmol) and tetrakis(triphenylphosphine)palladium (0) (87 mg, 0.075 mmol). Heat the mixture in a sealed tube at 60° C. overnight. Cool the reaction to room temperature and filter through diatomaceous earth. Concentrate the filtrate and purify the residue by silica gel chromatography, eluting with a gradient from 75:25 to 65:35 with a solution of (1:1 hexanes and dichloromethane):ethyl acetate to give the title compound as a yellow oil which crystallizes upon standing (309 mg, 78%).

Provenance & Evidence