Acetic Acid → N-{[4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]methyl}pyridin-3-amine

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Reaction Steps

A solution of 4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carbaldehyde (10.0 mg, 0.039 mmol), 3-aminopyridine (5.5 mg, 0.059 mmol), and acetic acid (50 μl) in 1,2-dichloroethane (1 ml) was stirred for 2 d. Sodium triacetoxyborohydride (24.8 mg, 0.117 mmol) was added and the mixture was stirred for 1 d. The mixture was diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate. The organic layer was filtered with isoElute and concentrated. The residue was purified by column chromatography on silica gel (methanol/ethyl acetate gradient) to give N-{[4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]methyl}pyridin-3-amine 1H NMR (500 MHz, CDCl3) δ 8.52 (s, 1H); 8.21 (s, 1H); 8.00 (d, 1H); 7.96 (s, 1H), 7.80 (s, 1H), 7.69 (d, 1H), 7.02 (d, 1H), 6.95 (d, 1H), 6.81 (s, 1H), 6.08 (t, 1H), 4.47 (s, 2H), 3.98 (s, 3H), 3.82 (s, 3H) LRMS (ESI) calculated for C18H19N6O [M+H]+, 335.2; found 335.1.

Provenance & Evidence