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

HRID 242
Notes
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Reaction equation

HRID 242 reaction equation
CN1Cc2ccc(Cl)nc2OC(c2ccccc2)C1.COc1cc(N)ccc1-n1cnc(C)c1>CC(=O)O.CC(=O)O.COCCOC.O=C([O-])[O-].[Cs+].[Cs+].[Pd].c1ccc(-c2ccccc2P(C2CCCCC2)C2CCCCC2)cc1>COc1cc(Nc2ccc3c(n2)OC(c2ccccc2)CN(C)C3)ccc1-n1cnc(C)c1
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 454801813-methoxy-4-(4-methyl-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 49819935N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amineYield 37.23%

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

8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (60.0 mg, 0.22 mmol), 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (57.7 mg, 0.28 mmol), palladium(II) acetate (4.90 mg, 0.02 mmol), 2-(Dicyclohexylphosphino)biphenyl (7.65 mg, 0.02 mmol) and CS2CO3 (213 mg, 0.66 mmol) were weighed into a microwave vial. The vial was capped and flushed with argon. DME (4 mL) was added and the mixture was heated to 100°C in a microwave apparatus for 1 h. The cooled reaction mixture was diluted with dichloromethane and methanol, filtered through a plug of Celite and the solvents were evaporated. The residue was purified by HPLC to give 36 mg (37 % Yield) of the title product.

Sources & evidence

ORD record
ord-e759108cf109420c9b96a1936ea5e56d
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Reaction notes

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On this pageParticipantsConditionsProcedureSources & evidenceReaction notes