Water → HCID 71547715, compound

HRID 570763Notes

Reaction equation

HRID 570763 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([Br:18])[C:3]=1[NH:19][C:20]([C:22]1[C:23]([O:38][CH3:39])=[C:24]([N:28]([CH3:37])[C:29]([C:31]2[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=2)=[O:30])[CH:25]=[CH:26][CH:27]=1)=[O:21].[H-].[Na+].I[CH3:43].O>CN(C)C=O>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:17])([C:9]([F:10])([F:11])[F:12])[C:13]([F:14])([F:15])[F:16])[CH:5]=[C:4]([Br:18])[C:3]=1[N:19]([CH3:43])[C:20]([C:22]1[C:23]([O:38][CH3:39])=[C:24]([N:28]([CH3:37])[C:29]([C:31]2[CH:32]=[CH:33][N:34]=[CH:35][CH:36]=2)=[O:30])[CH:25]=[CH:26][CH:27]=1)=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 89487982HCID 89487982, compound

Product 1

HCID 71547715HCID 71547715, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-[3-[[2,6-dibromo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-methoxy-phenyl]-N-methyl-pyridine-4-carboxamide (0.100 g, 0.145 mmole) in N,N-dimethylformamide (4 ml) was added sodium hydride (55% suspension in oil, 0.0067 g, 0.153 mmole). After the gas evolution had stopped, iodomethane (0.010 ml, 0.023 g, 0.160 mmole) was added. After 0.5 hour, the reaction mixture was poured on to water (15 ml) and the product was extracted with ethyl acetate. The organic solution was washed with water, then brine and dried over sodium sulfate. After removal of the solvent the crude was purified by column chromatography over silica gel using ethyl acetate-cyclohexane to yield the title compound (Compound G17 of Table G) as amorphous material showing by LC-MS analysis under the conditions 6 (described hereafter) a retention time of 1.09 min and a M+H+ mass of 700.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic solution was washed with water
  3. dry with materialbrine and dried over sodium sulfate
  4. customAfter removal of the solvent the crude
  5. customwas purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-edcd6ac3f47541b1afaf25117a9ea149
Source dataset
uspto-grants-2015_05
Patent number
US09023873B2

Reaction notes

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