6-Methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-ylamine → HCID 57512827, compound

Participants

Reaction Conditions

Reaction Steps

A reaction mixture of 8-chloro-4-methyl-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (0.605 g, 2.16 mmol), 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (0.440 g, 2.16 mmol), Cs2CO3 (1.053 g, 3.23 mmol), Tri-t-butylphosphonium tetrafluoroborate (0.063 g, 0.22 mmol) and Bis(dibenzylideneacetone)palladium (0.062 g, 0.11 mmol) in DME (20 mL) was flushed with argon and run in the microwave at 120°C for 60 minutes. Have unreacted startingmaterial left. Added Tri-t-butylphosphonium tetrafluoroborate (0.063 g, 0.22 mmol) and Bis(dibenzylideneacetone)palladium (0.062 g, 0.11 mmol) and ran the vial at 120°C for another hour. The mixture was filtered through celite and washed with DCM. The solvent was evaporated and the crude prouduct was purified by silica flash chromatography using a gradient of metanol (0 to 5%) in dichloromethane giving N-(6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-yl)-4-methyl-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine (0.483 g, 50.0 %).

Provenance & Evidence