Ethyl Acetate → 2,3,4,5-Tetrahydro-1,4-benzoxazepin-5-one

HRID 2366570Notes

Reaction equation

HRID 2366570 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[CH:11][C:12]3[O:18][CH2:17][CH2:16][NH:15][C:14](=[O:19])[C:13]=3[CH:20]=2)O1.BrC1C=CN(C)C(=O)C=1.C(=O)([O-])[O-].[Cs+].[Cs+].CCOC(C)=O>CN(C=O)C.O.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].Cl[Pd]Cl>[O:18]1[C:12]2[CH:11]=[CH:10][CH:9]=[CH:20][C:13]=2[C:14](=[O:19])[NH:15][CH2:16][CH2:17]1

Participants

9

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 221323964-Bromo-1-methylpyridin-2(1H)-oneHCID 711830947-(Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-5-one

Product 1

HCID 3406292,3,4,5-Tetrahydro-1,4-benzoxazepin-5-one

Reagents, catalysts & solvents 4

HCID 24290Palladium ChlorideCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one (200 mg, 0.69 mmol), 4-bromo-1-methylpyridin-2(1H)-one (156 mg, 0.83 mmol), cesium carbonate (674 mg, 2.07 mmol), 1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium (49 mg, 0.069 mmol) was dissolved in a degassed mixture of DMF and water 3/1.5 (4.5 mL). The mixture was heated in microwave at 85° C. for 40 min. The mixture was poured into EtOAc and washed with water and brine. The organic layer was collected, dried over sodium sulfate and loaded onto silica gel. A flash column (5% MeOH in EtOAc) and reverse phase chromatography gave 7-ethyl-2-oxo-1,2-dihydropyridin-4-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one.

Workup

  1. washwashed with water and brine
  2. customThe organic layer was collected
  3. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-cf0b1d4586684afdbcdbc04b19d5c4f0
Source dataset
uspto-grants-2014_04
Patent number
US08697863B2

Reaction notes

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