Methyl iodide → 2-(3,5-Bis-trifluoromethyl-phenyl)-N-[4-iodo-6-(4-methyl-piperazin-1-yl)-pyridin-3-yl]-N-methyl-isobutyramide

HRID 1348559Notes

Reaction equation

HRID 1348559 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([C:13]([CH3:32])([CH3:31])[C:14]([NH:16][C:17]2[CH:18]=[N:19][C:20]([N:24]3[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]3)=[CH:21][C:22]=2[I:23])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH3:35][Si]([N-][Si](C)(C)C)(C)C.[K+].IC>CN(C)C=O.O1CCCC1>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([C:13]([CH3:32])([CH3:31])[C:14]([N:16]([C:17]2[CH:18]=[N:19][C:20]([N:24]3[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]3)=[CH:21][C:22]=2[I:23])[CH3:35])=[O:15])[CH:4]=[C:3]([C:2]([F:1])([F:33])[F:34])[CH:8]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 210916402-(3,5-Bis-trifluoromethyl-phenyl)-N-[4-iodo-6-(4-methyl-piperazin-1-yl)-pyridin-3-yl]-isobutyramide

Product 1

HCID 210916412-(3,5-Bis-trifluoromethyl-phenyl)-N-[4-iodo-6-(4-methyl-piperazin-1-yl)-pyridin-3-yl]-N-methyl-isobutyramideYield 31%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.09 g (5.15 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-[4-iodo-6-(4-methyl-piperazin-1-yl)-pyridin-3-yl]-isobutyramide in 30 ml N,N-dimethylformamide were added at 0° C. 6.8 ml (6.2 mmol) of a 0.91 M solution of potassium bis(trimethylsilyl)amide in tetrahydrofuran. After stirring at 0° C. for 40 min 0.352 ml (5.66 mmol) iodomethane were added. The mixture was stirred for 2 days in a closed flask. The reaction mixture was concentrated in vacuo and purified by flash chromatography to give 980 mg (31%) of the title compound as a brown oil.

Workup

  1. additionwere added
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-d21304687d344c469bf0781504bb0076
Source dataset
uspto-grants-2007_05
Patent number
US07211579B2

Reaction notes

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