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

HRID 265Notes

Reaction equation

HRID 265 reaction equation
CN1Cc2ccc(Cl)nc2OC(C2CC2)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(C2CC2)CN(C)C3)ccc1-n1cnc(C)c1

Participants

7

Reactant 2

HCID 454801813-methoxy-4-(4-methyl-1H-imidazol-1-yl)anilineHCID 595778088-Chloro-2-cyclopropyl-4-methyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine

Product 1

HCID 498193712-cyclopropyl-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4-methyl-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

3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (0.031 g, 0.15 mmol), 8-chloro-2-cyclopropyl-4-methyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (0.036 g, 0.15 mmol), Palladium acetate (3.39 mg, 0.02 mmol), 2-(Dicyclohexylphosphino)biphenyl (5.29 mg, 0.02 mmol) and Cesium carbonate (0.049 g, 0.15 mmol) were added in a microwave vial. The mixture was capped and flushed with argon. 1,2-dimethoxyethane (2 mL) was added and the mixture was run in a microwave for 60 minutes at 100°C. Extremely little product was formed according to LCMS and all oxazepinestartingmaterial was consumed. Did not isolate, discarded.

Sources & evidence

ORD record
ord-8b7a42439bc84286a389b0a321434e15
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Reaction notes

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