Ethanamine, 2,2,2-trifluoro- → HCID 59320965, compound

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Reaction Conditions

Reaction Steps

A solution of 5-bromo-pyridin-3-ylamine (1.73 g, 10 mmol) and 4-nitrophenyl chloroformate (2.2 g, 11 mmol) in dry THF (40 ml) was stirred and heated at 60° C. under N2 for 3 hours. After cooling to RT, DIPEA (5.2 ml, 30 mmol) and 2,2,2-trifluoroethylamine (1.6 ml, 20 mmol) were added and the solution was stirred at RT for 16 hours. The volatiles were removed in vacuo and the residue was partitioned between EtOAc and 1N NaOH. The organic layer was washed with H2O (×1) and brine (×1), then dried (MgSO4), filtered and evaporated. The residue was triturated with CH2Cl2. The solid was collected by filtration, washed with Et2O and dried under vacuum to give the title compound (1.7 g) as a colourless solid. 1H NMR (400 MHz, DMSO-d6): 9.18 (1H, s), 8.49 (1H, d), 8.28 (1H, d), 8.25 (1H, t), 7.06 (1H, t), 3.99-3.88 (2H, m).

Provenance & Evidence