Methyl iodide → 3-(1-Ethyl-5-fluoro-indan-1-yl)-1-methyl-7-nitro-1H-indole

HRID 13701

Reaction equation

HRID 13701 reaction equation
[CH2:1]([C:3]1([C:13]2[C:21]3[C:16](=[C:17]([N+:22]([O-:24])=[O:23])[CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[CH2:5][CH2:4]1)[CH3:2].[CH3:25][O-].[Na+].IC>CN(C)C=O.CCOCC>[CH2:1]([C:3]1([C:13]2[C:21]3[C:16](=[C:17]([N+:22]([O-:24])=[O:23])[CH:18]=[CH:19][CH:20]=3)[N:15]([CH3:25])[CH:14]=2)[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[CH2:5][CH2:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 116095063-(1-Ethyl-5-fluoro-indan-1-yl)-7-nitro-1H-indole

Product 1

HCID 115736303-(1-Ethyl-5-fluoro-indan-1-yl)-1-methyl-7-nitro-1H-indoleYield 95.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Combine 3-(1-ethyl-5-fluoro-indan-1-yl)-7-nitro-1H-indole (0.33 g, 1.02 mmol), sodium methoxide (110 mg, 2.04 mmol), and iodomethane (0.10 ml, 1.53 mmol) in dimethylformamide (5 ml) and stir at room temperature under nitrogen overnight. Dilute with ether, wash with water (2×), dry over sodium sulfate, filter, and concentrate to obtain the title compound as a yellow amorphous solid (0.33 g, 94%). LC-MS m/z 339.1 (M++1).

Workup

  1. washwash with water (2×)
  2. dry with materialdry over sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-becbe1a517f8420a8d9ed13574665c82
Source dataset
uspto-grants-2010_06
Patent number
US07728150B2

Linked notes

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