4-(3-Methyl-1H-1,2,4-triazol-1-yl)aniline → (R)-4-Methyl-N-(4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine

HRID 212

Reaction equation

HRID 212 reaction equation
CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.Cc1ncn(-c2ccc(N)cc2)n1>CC(=O)O.CC(=O)O.COCCOC.O=C([O-])[O-].[Cs+].[Cs+].[Pd].c1ccc(-c2ccccc2P(C2CCCCC2)C2CCCCC2)cc1>Cc1ncn(-c2ccc(Nc3ccc4c(n3)O[C@H](c3ccccc3)CN(C)C4)cc2)n1

Participants

7

Reactant 2

HCID 446274764-(3-Methyl-1H-1,2,4-triazol-1-yl)anilineHCID 57512880(2R)-8-chloro-4-methyl-2-phenyl-3,5-dihydro-2H-pyrido[3,2-f][1,4]oxazepine

Product 1

HCID 49819370(R)-4-Methyl-N-(4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amineYield 0%

Reagents, catalysts & solvents 4

HCID 10796Cesium carbonateReagentHCID 27342162-(Dicyclohexylphosphino)biphenylCatalystHCID 4144353Palladium (II) acetateCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of (R)-8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (5.00 mg, 0.02 mmol) and 4-(3-methyl-1H-1,2,4-triazol-1-yl)aniline (3.17 mg, 0.02 mmol) in DME (.5 mL) was added via a syringe to a capped microwave vial containing PALLADIUM(II) ACETATE (0.409 mg, 1.82 µmol), 2-(DICYCLOHEXYLPHOSPHINO)BIPHENYL (0.638 mg, 1.82 µmol), CESIUM CARBONATE (8.89 mg, 0.03 mmol) and KI (1.511 mg, 9.10 µmol) under an argon atmosphere. The resulting mixture was heated to 100°C in a microwavwe apparatus for 1 h and analyzed by LCMS. No product.

Sources & evidence

ORD record
ord-7b17e577dfcd4694a98108d8e01246cd
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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