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

HRID 10
Notes
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Reaction equation

HRID 10 reaction equation
CN1Cc2ccc(Cl)nc2OC(c2ccccc2)C1.Nc1ccc(-n2ccnc2)cc1>CC(=O)O.CC(=O)O.COCCOC.O=C([O-])[O-].[Cs+].[Cs+].[Pd].c1ccc(-c2ccccc2P(C2CCCCC2)C2CCCCC2)cc1>CN1Cc2ccc(Nc3ccc(-n4ccnc4)cc3)nc2OC(c2ccccc2)C1
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 3201654-(1H-imidazol-1-yl)anilineHCID 595778668-Chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine

Product 1

HCID 49821013N-(4-(1H-imidazol-1-yl)phenyl)-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amineYield 41.47%

Reagents, catalysts & solvents 4

HCID 10796Cesium carbonateReagent
HCID 2734216
2-(Dicyclohexylphosphino)biphenyl
Catalyst
HCID 4144353Palladium (II) acetateCatalyst
HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

[Reactants], 8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (0.120 g, 0.44 mmol), Palladium(II) acetate (9.81 mg, 0.04 mmol), 2-(Dicyclohexylphosphino)biphenyl (0.015 g, 0.04 mmol) and Cesium carbonate (0.427 g, 1.31 mmol) in DME (2.5 mL) were placed in a microwave vial and flushed with argon. The reaction mixture was then run in the microwave at 100°C for 1 hr. Reaction not complete. Run for another 30 minutes in the microwave. Still not complete. Added 0.1 eq of Palladium(II)acetate and 0.1 eq of 2-(Dicyclohexylphosphino)biphenyl and let the reaction mixture run in the microwave for additional 45 minutes. Reaction complete. The reaction mixture was filtrated through celite and the filtrate was concentrated. The crude product was purified by preparative chromatography giving 0.072 g (41%) of the product. N-(4-(1H-imidazol-1-yl)phenyl)-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine

Sources & evidence

ORD record
ord-fa122fe6774f45c5b7a107c1460052d3
Source dataset
750 AstraZeneca ELN dataset
Original link
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Reaction notes

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