Acetic Acid → HCID 67028846, compound

Participants

Reaction Steps

To a suspension of 2-((6-chloro-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl)methylamino)pyrimidine-4-carbaldehyde (110 mg, 0.29 mmol) in CH2Cl2 (5 mL) was added acetic acid (0.5 mL) until the reaction became clear. Ethylamine (0.87 mmol, 3.0 eq) and Na(OAc)3BH (0.58 mmol, 2.0 eq) were added and the reaction mixture was stirred for 18 h at room temperature. After this time the reaction was diluted with CH2Cl2 (20 mL) and quenched by the addition of satd. aq. NaHCO3 (10 mL). After stirring for 10 min the layers were separated and the organic layer was dried over Na2SO4, filtered, concentrated and purified by reverse phase preparatory HPLC (silica gel, acetonitrile/water w/0.05% TFA) to afford the desired product. (0.060 g, 37% yield). M/e+ 411.1 for C21H20ClFN6 (M+H)+; 1H-NMR (500 MHz, CDCl3, δ) 8.48 (d, J=1.5 Hz, 1H), 8.29 (d, J=5.0 Hz, 1H), 7.78-7.75 (m, 2H), 7.58 (d, J=9.5 Hz, 1H), 7.21-7.15 (m, 3H), 6.70 (d, J=5.5 Hz, 1H), 5.24 (br s, 1H), 5.05 (d, J=5.5 Hz, 2H), 3.77 (s, 2H), 2.72 (q, J=7.5 Hz, 2H), 1.15 (t, J=7.5 Hz, 3H).

Provenance & Evidence