4-(1H-imidazol-1-yl)aniline → 8-(4-Imidazol-1-ylanilino)-4-methyl-2-phenyl-2,3-dihydropyrido[3,2-f][1,4]oxazepin-5-one

HRID 485

Reaction equation

HRID 485 reaction equation
CN1CC(c2ccccc2)Oc2nc(Cl)ccc2C1=O.Nc1ccc(-n2ccnc2)cc1>CC(=O)O.CC(=O)O.COCCOC.O=C([O-])[O-].[Cs+].[Cs+].[Pd].c1ccc(-c2ccccc2P(C2CCCCC2)C2CCCCC2)cc1>CN1CC(c2ccccc2)Oc2nc(Nc3ccc(-n4ccnc4)cc3)ccc2C1=O

Participants

7

Reactant 2

HCID 3201654-(1H-imidazol-1-yl)anilineHCID 595778258-Chloro-4-methyl-2-phenyl-3,4-dihydropyrido[3,2-F][1,4]oxazepin-5(2H)-one

Product 1

HCID 498202358-(4-Imidazol-1-ylanilino)-4-methyl-2-phenyl-2,3-dihydropyrido[3,2-f][1,4]oxazepin-5-oneYield 37.83%

Reagents, catalysts & solvents 4

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

Conditions

Temperature
100 °C

Procedure

8-chloro-4-methyl-2-phenyl-3,4-dihydropyrido[3,2-f][1,4]oxazepin-5(2H)-one (115 mg, 0.40 mmol), 4-(1H-imidazol-1-yl)aniline (95 mg, 0.60 mmol), PdOAc2 (8.94 mg, 0.04 mmol), biphenyl-2-yldicyclohexylphosphine (13.96 mg, 0.04 mmol) and CS2CO3 (389 mg, 1.19 mmol) were placed in a microwave vial equipped with a stirring bar. The vial was capped and flushed with argon. DME (1.5 mL) was added via a syringe and the mixture was heated to 100°C in a microwave apparatus for 1 h. The residue was diluted with ethyl acetate and filtered through a short plug og Celite. The filtrate was evaporated and the residue was purified by HPLC to give 62 mg of the product as a solid.

Sources & evidence

ORD record
ord-b03de5e7ee154175b8ccb76d7202e229
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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