(2R)-8-chloro-4-methyl-2-phenyl-3,5-dihydro-2H-pyrido[3,2-f][1,4]oxazepine → HCID 68757779, compound

HRID 408Notes

Reaction equation

HRID 408 reaction equation
CN1Cc2ccc(Cl)nc2O[C@H](c2ccccc2)C1.COc1nc(N)ccc1-c1ccc(=O)n(C)c1>C1COCCO1.CC(=O)O.CC(=O)O.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.CCC(C)(C)[O-].[Na+].[Pd]>COc1nc(Nc2ccc3c(n2)O[C@H](c2ccccc2)CN(C)C3)ccc1-c1ccc(=O)n(C)c1

Participants

7

Reactant 2

HCID 57512880(2R)-8-chloro-4-methyl-2-phenyl-3,5-dihydro-2H-pyrido[3,2-f][1,4]oxazepineHCID 57512934HCID 57512934, compound

Product 1

HCID 68757779HCID 68757779, compoundYield 35.11%

Reagents, catalysts & solvents 4

HCID 2733478Sodium 2-methylbutan-2-olateReagentHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 4144353Palladium (II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

(R)-8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (300 mg, 1.09 mmol), 5-(6-amino-2-methoxypyridin-3-yl)-1-methylpyridin-2(1H)-one (253 mg, 1.09 mmol), Palladium(II) acetate (24.51 mg, 0.11 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (63.2 mg, 0.11 mmol) and Sodium tert-pentoxide (144 mg, 1.31 mmol) were mixed in dioxane (3 mL) and run in a microwave reactor for 40 min at 120°C. the mixture was filtered thru celite and concetrated. purified using flash column chromatography using 0-6 % MeOH (1% NH3) in DCM.

Sources & evidence

ORD record
ord-2b09b0edd9af4f8e80b89621d51beb35
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Reaction notes

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