Dimethylformamide → HCID 11143579, compound

HRID 1503825Notes

Reaction equation

HRID 1503825 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])C(N)=[C:4]([F:10])[CH:3]=1.[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)(O)[O-].[K+].C(O[CH2:28][CH3:29])(=O)C.[CH3:30][N:31]([CH3:34])C=O>>[CH2:11]([N:31]([CH2:34][C:29]1[CH:28]=[CH:4][CH:3]=[CH:2][CH:7]=1)[C:30]1[C:4]([F:10])=[CH:3][C:2]([Br:1])=[CH:7][C:6]=1[F:8])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 516893Potassium BicarbonateHCID 6101914-Bromo-2,6-difluoroaniline

Product 1

HCID 11143579HCID 11143579, compound

Procedure

A mixture of the product of Example 16A (1.1 g, 5.3 mmol), benzyl bromide (949 mg, 0.66 ml) and potassium bicarbonate (1.46 mg, 10.6 mmol) in N,N-dimethylformamide (3 mL) was stirred at ambient temperature until TLC indicated no starting material remained. Ethyl acetate was added, and the mixture was washed with water and brine and dried over anhydrous sodium sulfate. After filtration and concentration, the residue was purified by flash chromatography on silica gel (200-300 mesh) eluting with 10/1 petroleum ether/dichloromethane to give the title compound.

Workup

  1. washthe mixture was washed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationAfter filtration and concentration
  4. customthe residue was purified by flash chromatography on silica gel (200-300 mesh)
  5. washeluting with 10/1 petroleum ether/dichloromethane

Sources & evidence

ORD record
ord-f51c873fa1d64b53b734644796002794
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

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