4-Methyl-5-[[2-(1-methyl-1h-pyrazol-4-yl)-4-pyridinyl]oxy]-2-nitropyridine → 4-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-amine

Participants

Reaction Steps

A solution of 4-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)-2-nitropyridine (0.83 g, 2.67 mmol) in EtOAc (20 mL) was treated with palladium on carbon (50% wet, 0.284 g, 0.267 mmol) and hydrogenated (1 atm) overnight. The solids were removed via filtration through diatomaceous earth, rinsed well with EtOAc and the filtrate was concentrated to dryness to afford crude 4-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-amine (750 mg, 100%) as a white amorphous solid which was carried on to the next step without further purification. 1H NMR (400 MHz, DMSO-d6): δ 8.30 (d, J=5.7 Hz, 1H), 8.23 (s, 1H), 7.93 (d, J=0.7 Hz, 1H), 7.69 (s, 1H), 7.12 (d, J=2.4 Hz, 1H), 6.51 (dd, J=5.7, 2.4 Hz, 1H), 6.39 (s, 1H), 5.91 (s, 2H), 3.84 (s, 3H), 1.95 (s, 3H); MS (ESI) m/z: 282.1 (M+H+).

Provenance & Evidence