4-tert-Butylbenzylamine → HCID 67273904, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl 2-chloro-3-pyridinecarboxylate (0.610 g, 3.29 mmol) in ethanol (10.0 mL) was treated with 4-tert-butylbenzylamine (0.580 mL, 3.29 mmol). The mixture was heated to 160° C. for 1 h in a Biotage Initiator microwave synthesizer. The solution was diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate. The organic portion was dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification via flash column chromatography (20-60% ethyl acetate in hexanes) afforded the title compound clear yellow oil (0.461 g, 45%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.34 (dd, J=4.8, 1.8 Hz, 1H), 8.18 (dd, J=7.8, 2.0 Hz, 1H), 7.30-7.42 (m, 4H), 6.58 (dd, J=7.6, 4.8 Hz, 1H), 4.75 (d, J=5.6 Hz, 2H), 4.34 (q, J=7.1 Hz, 2H), 1.39 (t, J=7.2 Hz, 3H), 1.34 (s, 9H). MS(ES+) m/e 313 [M+H]+.

Provenance & Evidence