COc1nc(N)ccc1-c1cnn(C)c1.Cc1csc(C2Oc3nc(Cl)ccc3CN(C)C2C)n1>CC(=O)O.CC(=O)O.COCCOC.O=C([O-])[O-].[Cs+].[Cs+].[Pd].c1ccc(-c2ccccc2P(C2CCCCC2)C2CCCCC2)cc1>COc1nc(Nc2ccc3c(n2)OC(c2nc(C)cs2)C(C)N(C)C3)ccc1-c1cnn(C)c1
To 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (0.086 g, 0.42 mmol) in DME (3 mL) were 8-chloro-3,4-dimethyl-2-(4-methylthiazol-2-yl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (0.130 g, 0.42 mmol), cesium carbonate (0.205 g, 0.63 mmol), 2-(Dicyclohexylphosphino)biphenyl (0.015 g, 0.04 mmol) and Palladium acetate (9.42 mg, 0.04 mmol) added. The reaction was heated to 110°C for 60 min under argon atmosphere. The reaction mixture was filtered through celite, washed with DCM and the solvents were evaporated. The crude product was purified by silica flash chromatography, MeOH, 0-5%, in DCM yielding N-(6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-yl)-3,4-dimethyl-2-(4-methylthiazol-2-yl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine (0.147 g, 73.4 %). The product was submitted to the prepgroup for chiral separation.
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