Methyl iodide → HCID 70562743, compound

HRID 1427223Notes

Reaction equation

HRID 1427223 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:13]2[C:21]3[C:16](=[C:17]([N:22]4[C:26]([CH3:27])=[CH:25][CH:24]=[C:23]4[CH3:28])[CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)([CH2:11][CH3:12])[CH2:9][OH:10])=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:32]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:13]2[C:21]3[C:16](=[C:17]([N:22]4[C:26]([CH3:27])=[CH:25][CH:24]=[C:23]4[CH3:28])[CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)([CH2:11][CH3:12])[CH2:9][O:10][CH3:32])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 70563490HCID 70563490, compound

Product 1

HCID 70562743HCID 70562743, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(4-chlorophenyl)-2-(4-(2,5-dimethyl-1H-pyrrol-1-yl)-1H-indol-1-yl)butan-1-ol (89 mg) in dry DMF (3 mL) was treated by NaH (60% in oil, 18 mg) at 0° C. for 30 min, then was added iodomethane (97 mg). The mixture was stirred at room temperature for 2 h. The solution was quenched with saturated ammonium chloride solution, and extracted with ethyl acetate (25 mL). The organic layers was washed with brine, dried over sodium sulfate, and evaporated to afford the title compound as a white solid. LC/MS m/z=407.1 [M+H]+.

Workup

  1. customThe solution was quenched with saturated ammonium chloride solution
  2. extractionextracted with ethyl acetate (25 mL)
  3. washThe organic layers was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-d86563c35be14c0fa2447a377bac66c2
Source dataset
uspto-grants-2015_01
Patent number
US08933113B2

Reaction notes

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