Aniline → HCID 56926092, compound

Participants

Reaction Steps

To a solution of 2,2-dimethyl-2H-pyrano[2,3-b]pyridine-6-carbaldehyde 18 (20 mg, 0.106 mg) in methanol (1 ml) was added aniline (0.01 mL, 0.12 mmol), NaCNBH3 (13 mg, 0.212 mmol) and ZnCl2 (29 mg, 0.212 mmol). The reaction was stirred for 30 minutes after which the solvent was removed by rotary evaporation and the 1M NaOH added to the residue, extracted with DCM, dried over MgSO4 and concentrated in vacuo. Purified by column chromatography (3:1 Hx/EtOAc) to give a white solid 20 mg (72%). 1H NMR (CDCl3) δ 8.01 (s, 1H), 7.29 (s, 1H), 7.26-7.16 (m, 2H), 6.74 (t, J=7.2 Hz, 1H), 6.63 (d, J=8.0 Hz, 1H), 6.26 (d, J=9.6 Hz, 1H), 5.67 (d, J=9.6 Hz, 1H), 4.21 (s, 2H), 1.51 ppm (s, 6H). 13C NMR (CDCl3) δ 159.6, 147.8, 146.4, 133.8, 132.2, 129.3, 128.4, 120.9, 118.0, 115.4, 113.0, 79.2, 45.4, 28.8 ppm. HRMS (ESI) m/z calcd for C11H11NO2 [(M+H)+] 190.0868. found: 190.0870.

Provenance & Evidence