Methanol → HCID 58996249, compound

Participants

Reaction Conditions

Reaction Steps

Sodium azide (26.5 mg, 0.41 mmol) was added to a solution of methyl 3,4-dichloro-6-(1,1-difluroethyl)pyridine-2-carboxylate (100 mg, 0.37 mmol) in dimethylformamide (2 mL) and water (0.2 mL). After the reaction mixture was stirred at 50° C. for 5 hours, it was quenched with water and extracted with ethyl ether. The orgainc phase was dried and concentrated to provide the crude 4-azide compound. It was immediately taken up into methanol (2 mL) and sodium borohydride (21 mg, 0.55 mmol) was carefully added. After stirring for 10 minutes, water was added and the mixture concentrated. Ethyl acetate was added and the mixture washed with brine. The organic layer was dried (MgSO4), filtered and concentrated to dryness. The crude product was purified by column chromatography (20% ethyl acetate in hexane) to give methyl 4-amino-3-chloro-6-(1,1-difluroethyl)pyridine-2-carboxylate (53 mg, 0.21 mmol) as an oil; 1H NMR (CDCl3): δ 7.04 (s, 1H), 4.92 (b.s, 2H), 3.98 (s, 3H), 1.97 (t, d=18.7 Hz, 3H).

Provenance & Evidence