Tetrahydrofuran → HCID 66699704, compound

Participants

Reaction Steps

(R)-6-Chloro-3-nitro-N-(1-phenylethyl)pyridin-2-amine. To a solution of 2,6-dichloro-3-nitropyridine (1.0 g, 5.18 mmol) in tetrahydrofuran (8 mL) at −78° C. was added diisopropylethylamine (1.08 mL, 6.22 mmol) followed by (R)-1-phenylethanamine (0.75 g, 6.22 mmol) in tetrahydrofuran (2 mL). The reaction was kept at −78° C. for 2 h and then allowed to slowly warm to room temperature overnight. The solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography to afford the title compound (1.12 g, 78% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.67 (d, J=7.5, 1H), 8.43 (d, J=8.5, 1H), 7.46 (d, J=7.5, 2H), 7.35 (t, J=7.5, 2H), 7.25 (t, J=7.5, 1H), 6.80 (d, J=8.5, 1H), 5.38 (app quint, J=7, 1H), 1.59 (d, J=7, 3H).

Provenance & Evidence