1,4-Dioxane → HCID 68578580, compound

HRID 886897Notes

Reaction equation

HRID 886897 reaction equation
Br[C:2]1[CH:19]=[CH:18][C:5]2[CH2:6][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8][CH2:9][O:10][C:4]=2[CH:3]=1.[CH3:20][C@H:21]1[O:26][C@@H:25]([CH3:27])[CH2:24][NH:23][CH2:22]1.CC(C)([O-])C.[Na+].O1CCOCC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.O>[CH3:27][C@H:25]1[O:26][C@@H:21]([CH3:20])[CH2:22][N:23]([C:2]2[CH:19]=[CH:18][C:5]3[CH2:6][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8][CH2:9][O:10][C:4]=3[CH:3]=2)[CH2:24]1

Participants

8

Reactant 4

HCID 312751,4-DioxaneHCID 6415002,6-Dimethylmorpholine, cis-HCID 23676156Sodium t-butoxideHCID 68578192HCID 68578192, compound

Product 1

HCID 68578580HCID 68578580, compoundYield 135.9%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylCatalystHCID 962WaterSolvent

Procedure

A solution of tert-butyl 8-bromo-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (300 mg, 0.609 mmol), cis-2,6-dimethylmorpholine (0.370 ml, 3.00 mmol), X-phos (26.1 mg, 0.0548 mmol), tris(dibenzylideneacetone)dipalladium(0) (16.6 mg, 0.0181 mmol), sodium tert-butoxide (131 mg, 1.37 mmol) and dioxane (6 ml) was stirred under an argon atmosphere for 2 hr at 80° C. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give the desired product (300 mg, 90.4%) as an oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-c1e08a59f79146abb54cf93de9e8ee45
Source dataset
uspto-grants-2012_08
Patent number
US08247403B2

Reaction notes

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