Methyl iodide → 7-Oxo-4,5,6,7-tetrahydro-benzo[b]thiophene-3-sulfonic acid [2-(2,4-difluorophenyl)-2-hydroxy-ethyl]-methyl-amide

HRID 1351279Notes

Reaction equation

HRID 1351279 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]([OH:25])[CH2:10][NH:11][S:12]([C:15]1[C:16]2[CH2:23][CH2:22][CH2:21][C:20](=[O:24])[C:17]=2[S:18][CH:19]=1)(=[O:14])=[O:13].[C:26](=O)([O-])[O-].[K+].[K+].CI.C(OCC)(=O)C>CN(C)C=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]([OH:25])[CH2:10][N:11]([CH3:26])[S:12]([C:15]1[C:16]2[CH2:23][CH2:22][CH2:21][C:20](=[O:24])[C:17]=2[S:18][CH:19]=1)(=[O:14])=[O:13]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 210986777-Oxo-4,5,6,7-tetrahydro-benzo[b]thiophene-3-sulfonic acid [2-(2,4-difluorophenyl)-2-hydroxy-ethyl]-amide

Product 1

HCID 210986787-Oxo-4,5,6,7-tetrahydro-benzo[b]thiophene-3-sulfonic acid [2-(2,4-difluorophenyl)-2-hydroxy-ethyl]-methyl-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-oxo-4,5,6,7-tetrahydro-benzo[b]thiophene-3-sulfonic acid[2-(2,4-difluorophenyl)-2-hydroxy-ethyl]-amide (the compound of Preparation Example 51) (197 mg) in N,N-dimethylformamide (3 mL) was added potassium carbonate (140 mg) and methyl iodide (0.1 mL). After stirring at room temperature for 1 hour, ethyl acetate was added, and the precipitate was removed by filtration. The solvent was evaporated at reduced pressure. Purification was carried out by silica gel column chromatography (hexane/ethyl acetate), and the title compound (190 mg) was obtained as a colorless candy-like substance.

Workup

  1. customthe precipitate was removed by filtration
  2. customThe solvent was evaporated at reduced pressure
  3. customPurification

Sources & evidence

ORD record
ord-03d59c623a5d46f092cf9112eb25dd94
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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