Sodium hydride → HCID 21468877, compound

HRID 1938616Notes

Reaction equation

HRID 1938616 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, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (5 moles, 200 mg of 60% in mineral oil) was added to 5-(2-cyanophenyl)indole (4.6 moles, 1.0 g. ) in 50 ml DMF and stirred for 45 minutes. 1-Bromo-1-(4-trifluoromethylphenyl)pentane (5 moles, 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 which 10% ethyl acetate in hexane to yield mg of 5-(2-cyanophenyl)-1-[1-(4-trifluoromethylphenyl)-1-pentyl]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 which 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-1e7e7d24a52d4b68aa980f3574f472b1
Source dataset
uspto-grants-1997_12
Patent number
US05693633

Reaction notes

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