Diisopropyl Ether → phenylthieno[2,3-b][1,5]benzoxazepin-4(5H)-one

HRID 650001

Reaction equation

HRID 650001 reaction equation
Br[C:2]1[S:16][C:5]2[O:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[NH:9][C:10](=[O:11])[C:4]=2[CH:3]=1.B([O-])([O-])O[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(OC(C)C)(C)C.C(OCC)(=O)C>C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1.C(O)C.[Pd]>[C:19]1([C:2]2[S:16][C:5]3[O:6][C:7]4[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=4[NH:9][C:10](=[O:11])[C:4]=3[CH:3]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

9

Reactant 4

HCID 7914Diisopropyl EtherHCID 8857Ethyl AcetateHCID 184221932-Bromothieno[2,3-b][1,5]benzoxazepin-4(5H)-oneHCID 19793864Phenylborate

Product 1

HCID 18422186phenylthieno[2,3-b][1,5]benzoxazepin-4(5H)-oneYield 83.8%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 10340Sodium CarbonateSolvent

Procedure

2-Bromothieno[2,3-b][1,5]benzoxazepin-4(5H)-one (1.0 g) was dissolved in 2M sodium carbonate (8 ml)-toluene (8 ml)-ethanol (8 ml) and phenyl borate (620 mg) and tetrakstriphenylphosphine palladium (390 mg) were added. The mixture was stirred under reflux with heating for 80 minutes. The reaction system was cooled to room temperature and diisopropyl ether and ethyl acetate were added. The precipitated crystals were collected by filtration and the obtained crystals were washed with ethyl acetate and water to give phenylthieno[2,3-b][1,5]benzoxazepin-4(5H)-one (830 mg).

Workup

  1. additionwere added
  2. temperatureunder reflux
  3. temperaturewith heating for 80 minutes
  4. filtrationThe precipitated crystals were collected by filtration
  5. washthe obtained crystals were washed with ethyl acetate and water

Sources & evidence

ORD record
ord-b04ddccd5c894e45a90bb6cdb81f3a2a
Source dataset
uspto-grants-2001_08
Patent number
US06271225B1

Linked notes

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