Trimethylsilyldiazomethane → Methyl 6-fluoropyridine-3-carboxylate

Participants

Reaction Steps

To a solution of 6-fluoronicotinic acid (255 mg, 1.32 mmol) in methanol (5 mL) at room temperature was added (trimethylsilyl)diazomethane (4.0 mL, 2 M in diethyl ether, 8.0 mmol). The reaction mixture was stirred at room temperature for 30 min and concentrated. Methyl 6-fluoronicotinate (129 mg, 47%) was used without further purification: NMR (600 MHz, DMSO-d6) δ 8.79 (d, J=2.6 Hz, 1H), 8.47 (td, J=7.9, 2.6 Hz, 1H), 7.35 (ddd, J=8.5, 2.6, 0.6 Hz, 1H), 3.88 (s, 3H); ESIMS calcd 156.0 (M++H), found 156.1 (M++H).

Provenance & Evidence