Sodium hydride → HCID 21468877, compound

HRID 743896Notes

Reaction equation

HRID 743896 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[CH:14]2)#[N:4].Br[CH:21]([C:26]1[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=1)[CH2:22][CH2:23][CH2:24][CH3:25]>CN(C=O)C>[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH:21]([C:26]1[CH:31]=[CH:30][C:29]([C:32]([F:33])([F:34])[F:35])=[CH:28][CH:27]=1)[CH2:22][CH2:23][CH2:24][CH3:25])[CH:15]=[CH:14]2)#[N:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 21468864HCID 21468864, compoundHCID 21468934HCID 21468934, compound

Product 1

HCID 21468877HCID 21468877, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (5 mmoles, 200 mg of 60% in mineral oil) was added to 5-(2-cyanophenyl)indole (4.6 mmoles, 1.0 g.) in 50 ml DMF and stirred for 45 minutes. 1-Bromo-1-(4-trifluoromethylphenyl)pentane (5 mmoles, 1.44 g) was added. The reaction was stirred at room temperature overnight, poured into ice water, and extracted into ethyl acetate. The organic layer was dried over sodium sulfate and concentrated. The intermediate was chromatographed over silica gel eluted with 10% ethyl acetate in hexane to yield 820 mg of 5-(2-cyanophenyl)-1-[1-(4-trifluoromethylphenyl)-1pentyl]indole.

Workup

  1. stirringThe reaction was stirred at room temperature overnight
  2. extractionextracted into ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe intermediate was chromatographed over silica gel
  6. washeluted with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-51a57dd122984d359f63ceb88bd19db4
Source dataset
uspto-grants-1996_09
Patent number
US05556981

Reaction notes

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