Methyl iodide → HCID 58288489, compound

HRID 1969071Notes

Reaction equation

HRID 1969071 reaction equation
[CH3:1][O:2][C:3](=[O:43])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=2[CH2:22][N:23]([CH2:41][CH3:42])[S:24]([C:27]2[CH:32]=[CH:31][C:30]([NH:33][C:34]3[CH:35]=[C:36]([CH3:40])[CH:37]=[CH:38][CH:39]=3)=[CH:29][CH:28]=2)(=[O:26])=[O:25])[CH:6]=1.[H-].[Na+].I[CH3:47]>C1COCC1>[CH3:1][O:2][C:3](=[O:43])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:21])[F:20])=[CH:14][C:13]=2[CH2:22][N:23]([CH2:41][CH3:42])[S:24]([C:27]2[CH:32]=[CH:31][C:30]([N:33]([CH3:47])[C:34]3[CH:35]=[C:36]([CH3:40])[CH:37]=[CH:38][CH:39]=3)=[CH:29][CH:28]=2)(=[O:26])=[O:25])[CH:6]=1

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 67221076HCID 67221076, compound

Product 1

HCID 58288489HCID 58288489, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To [3-(2-{[ethyl-(4-m-tolylamino-benzenesulfonyl)-amino]-methyl}-4-trifluoromethyl-phenoxy)-phenyl]-acetic acid methyl ester (0.080 g, 0.13 mmol) in THF (2 mL) under N2 was added sodium hydride (60% in mineral oil; 0.016 g, 0.39 mmol), and the mixture was stirred for 30 minutes at room temperature. Iodomethane (0.02 mL, 0.39 mmol) was added, and the reaction was stirred at room temperature for 4 hours. Analytical LCMS indicated that some starting material remained, so additional sodium hydride (60% in mineral oil; 0.008 g, 0.20 mmol)) and iodomethane (0.01 mL, 0.20=01) was added, and the reaction was stirred for 30 minutes and then taken directly to the hydrolysis step as a solution in THF.

Workup

  1. stirringthe reaction was stirred at room temperature for 4 hours
  2. stirringthe reaction was stirred for 30 minutes

Sources & evidence

ORD record
ord-b7a4ac2fb2914b93b3ef515640eb1d3b
Source dataset
uspto-grants-2013_04
Patent number
US08426449B2

Reaction notes

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