Methyl iodide → HCID 86603021, compound

HRID 735456Notes

Reaction equation

HRID 735456 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]1[CH:12]=[C:13]([C:17]3[N:18]([CH2:30][C:31]4[C:36]([F:37])=[CH:35][C:34]([F:38])=[CH:33][C:32]=4[F:39])[N:19]=[C:20]4[C:25]=3[CH:24]=[CH:23][CH:22]=[C:21]4[C:26]([F:29])([F:28])[F:27])[CH:14]=[CH:15][CH:16]=1)=[CH:5]2.[H-].[Na+].I[CH3:43]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:43])[C:6]([C:11]1[CH:12]=[C:13]([C:17]3[N:18]([CH2:30][C:31]4[C:36]([F:37])=[CH:35][C:34]([F:38])=[CH:33][C:32]=4[F:39])[N:19]=[C:20]4[C:25]=3[CH:24]=[CH:23][CH:22]=[C:21]4[C:26]([F:27])([F:28])[F:29])[CH:14]=[CH:15][CH:16]=1)=[CH:5]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86603019HCID 86603019, compound

Product 1

HCID 86603021HCID 86603021, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-[3-(5-fluoro-1H-indol-2-yl)phenyl]-2-(2,4,6-trifluorobenzyl)-7-(trifluoromethyl)-2H-indazole (0.03 g, 0.056 mmol) in 2 mL THF was treated with sodium hydride (0.004 g, 0.1 mmol, 60% in oil). The reaction mixture was stirred for 20 minutes and treated with iodomethane (0.007 mL, 0.1 mmol). Stirring was continued for 1 hour. The reaction mixture was concentrated and purified by normal phase HPLC (silica, hexane-EtOAC, 19:1) to give 0.01 g of product as a white solid.

Workup

  1. stirringStirring
  2. waitwas continued for 1 hour
  3. concentrationThe reaction mixture was concentrated
  4. custompurified by normal phase HPLC (silica, hexane-EtOAC, 19:1)

Sources & evidence

ORD record
ord-e0290cef8c04442abdcbd642018af890
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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