3-Iodobenzyl alcohol → HCID 67047723, compound

Participants

Reaction Conditions

Reaction Steps

Add a 1 M solution of tetrabutylammonium fluoride in THF (3.33 mL, 3.33 mmol) to a solution of 5-trimethylsilanylethynyl-nicotinonitrile, (prepared as described in PREPARATION 3), (0.801 g, 4.00 mmol), in tetrahydrofuran (8.3 mL) and triethylamine (3.34 mL). After 5 min add zinc (II) bromide (1.56 g, 5.99 mmol), 3-iodobenzyl alcohol (0.42 mL, 3.33 mmol), and tetrakis(triphenylphosphine)palladium (0) (269 mg, 0.233 mmol). Heat to 55° C. for 2 h, cool to room temperature, and filter through diatomaceous earth. Purify by silica gel chromatography, eluting with 80:20 to 60:40 (1:1 hexanes:dichloromethane):ethyl acetate, to give the title compound as a yellow crystalline solid (380 mg, 49%).

Provenance & Evidence