Isopropyl iodide → Ethyl 5-iodo-6-isopropoxynicotinate

Participants

Reaction Conditions

Reaction Steps

To a solution of 500 mg (1.71 mmol) of ethyl 6-hydroxy-5-iodonicotinate (from Step A) in 10 mL of DMF were added 330 mg (1.96 mmol) of 2-iodopropane and 1.67 g (5.11 mmol) of cesium carbonate. After stirring at 50° C. for 16 h, the reaction mixture was partitioned between EtOAc (20 mL) and water (20 mL). The organic layer was washed with brine (3×20 mL), dried over MgSO4, and concentrated. Chromatography on a Biotage 25+M cartridge using 4:1 v/v hexanes/EtOAc as the eluant to afford 210 mg (37%) of a white solid as the title compound: 1H NMR (500 MHz, CDCl3) δ 1.40 (m, 9H), 4.37 (q, J=7.1, 2H), 5.37 (m, 1H), 8.59 (d, J=2.1, 1H), 8.74 (d, J=2.0, 1H).

Provenance & Evidence