6-Methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-ylamine → HCID 57512827, compound
Reaction equation
CN1Cc2ccc(Cl)nc2OC(CC(F)(F)F)C1.COc1nc(N)ccc1-c1cnn(C)c1>CC(C)(C)P(C(C)(C)C)C(C)(C)C.COCCOC.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd]>COc1nc(Nc2ccc3c(n2)OC(CC(F)(F)F)CN(C)C3)ccc1-c1cnn(C)c1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 120 °C
Procedure
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 %).
Sources & evidence
- ORD record
- ord-41f70b81482a4604b6fa5a5e06a3c5e0
- Source dataset
- 750 AstraZeneca ELN dataset
- Original link
- View source
Reaction notes
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