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(=O)O.CC(=O)O.COCCOC.O=C([O-])[O-].[Cs+].[Cs+].[Pd].c1ccc(-c2ccccc2P(C2CCCCC2)C2CCCCC2)cc1>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
- 100 °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 (0.341 g, 1.21 mmol), 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (0.248 g, 1.21 mmol), PALLADIUM(II) ACETATE (0.027 g, 0.12 mmol), 2-(DICYCLOHEXYLPHOSPHINO)BIPHENYL (0.043 g, 0.12 mmol) and Cs2CO3 (0.594 g, 1.82 mmol) in DME (2 mL) was degassed and flushed with argon in a microwave vial. The reaction mixture was stirred at 110°C for 1 hr. The reaction mixture was filtrated through celite, washed with DCM and concentrated. The crude product was purified by silica flash chromatography using a gradient of methanol (0 to 5%) in DCM 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 (0.200 g, 36.7 %).
Sources & evidence
- ORD record
- ord-1b74a22b0fac45709f44bd49ada94b7f
- Source dataset
- 750 AstraZeneca ELN dataset
- Original link
- View source
Reaction notes
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