Dimethylformamide → Methyl 1-(4-ethynyl-3-fluorobenzyl)azetidine-3-carboxylate

Participants

Reaction Steps

Methyl 1-(3-fluoro-4-(2-(trimethylsilyl)ethynyl)benzyl)azetidine-3-carboxylate (20.9 g, 65 mmol) and cesium fluoride (11 g, 72 mmol) were added to DMF (50 mL). MeOH (100 mL) was added. After 2 h, MeOH was removed and the mixture was extracted with DCM and water. The organic layer was washed with brine and dried over magnesium sulfate. The solvent was removed and the material was purified by Biotage (75 L, 7-100% EtOAc/hexanes), affording methyl 1-(4-ethynyl-3-fluorobenzyl)azetidine-3-carboxylate as light yellow oil. MS (ESI) m/z: Calculated: 247.1; Observed: 248.0 (M++1). 1-(4-(2-(5-Benzylpyridin-2-yl)ethynyl)-3-fluorobenzyl)azetidine-3-carboxylic acid and 1-(4-(2-(5-Benzylpyridin-2-yl)ethyl)-3-fluorobenzyl)azetidine-3-carboxylic acid

Provenance & Evidence