Water → HCID 67050690, compound

HRID 1629089Notes

Reaction equation

HRID 1629089 reaction equation
[CH:1](I)([CH3:3])[CH3:2].[Br:5][C:6]1[CH:25]=[CH:24][C:9]2[C:10]3[N:11]([CH:15]=[C:16]([C:18]4[NH:19][CH:20]=[C:21]([CH3:23])[N:22]=4)[N:17]=3)[CH2:12][CH2:13][O:14][C:8]=2[CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[Br:5][C:6]1[CH:25]=[CH:24][C:9]2[C:10]3[N:11]([CH:15]=[C:16]([C:18]4[N:19]([CH:1]([CH3:3])[CH3:2])[CH:20]=[C:21]([CH3:23])[N:22]=4)[N:17]=3)[CH2:12][CH2:13][O:14][C:8]=2[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 178430850HCID 178430850, compound

Product 1

HCID 67050690HCID 67050690, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Isopropyl iodide (165 uL, 1.65 mmol) was added to a mixture of 417 mg (1.21 mmol) of 9-bromo-2-(4-methyl-1H-imidazol-2-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine and cesium carbonate (538 mg, 1.65 mmol) in 3 ml of N,N-dimethylformamide. The reaction mixture was stirred at room temperature for 18 hours, mixed with water and extracted with ethyl acetate. The organic extract was washed with water, brine, dried over MgSO4, concentrated, and purified on 4 g silica column eluting with 4-5% methanol in DCM to give 210 mg of 9-bromo-2-(1-isopropyl-4-methyl-1H-imidazol-2-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine. MS: 387.1.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. custompurified on 4 g silica column
  7. washeluting with 4-5% methanol in DCM

Sources & evidence

ORD record
ord-8a88589c5ef04a67aa4b97603b63b59a
Source dataset
uspto-grants-2014_07
Patent number
US08785626B2

Reaction notes

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