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

HRID 495

Reaction equation

HRID 495 reaction equation
CN1CC(c2ccccc2)Oc2nc(Cl)ccc2C1=O.Cc1nccn1-c1ccc(N)cc1>CC(=O)O.CC(=O)O.COCCOC.O=C([O-])[O-].[Cs+].[Cs+].[Pd].c1ccc(-c2ccccc2P(C2CCCCC2)C2CCCCC2)cc1>Cc1nccn1-c1ccc(Nc2ccc3c(n2)OC(c2ccccc2)CN(C)C3=O)cc1

Participants

7

Reactant 2

HCID 31574784-(2-methyl-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 498200844-methyl-8-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-2-phenyl-3,4-dihydropyrido[3,2-f][1,4]oxazepin-5(2H)-oneYield 42.31%

Reagents, catalysts & solvents 4

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

Conditions

Temperature
100 °C

Procedure

were placed in a microwave vial equipped with a stirring bar. The vial was capped and flushed with argon. DME (2 mL) was added via a syringe and the mixture was heated to 100°C in a microwave apparatus for 1h. The reaction mixture was filtered, the solvent was evaporated and the residue was purified by HPLC to give 53 mg (42 % yield) of the product as a solid.

Sources & evidence

ORD record
ord-1df95b34548d48fe94a49234436e46e5
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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