Water → 1-[3-{2(E)-(Quinolin-2-yl)ethenyl}benzyl]indole-7-carboxaldehyde

HRID 1198538Notes

Reaction equation

HRID 1198538 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][CH:9]=[CH:8]2)=[O:2].[H-].[Na+].[N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1/[CH:24]=[CH:25]/[C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29]Cl.O>CN(C)C=O.C1COCC1>[N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1/[CH:24]=[CH:25]/[C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29][N:10]1[C:11]2[C:7](=[CH:6][CH:5]=[CH:4][C:3]=2[CH:1]=[O:2])[CH:8]=[CH:9]1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2734629Indole-7-carboxaldehydeHCID 199590993-[2(E)-(Quinolin-2-yl)ethenyl]benzyl chloride

Product 1

HCID 191025811-[3-{2(E)-(Quinolin-2-yl)ethenyl}benzyl]indole-7-carboxaldehyde

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7-formyl indole (Example 10a (iv) (2 g, 13.8 mmole) in dry dimethyl formamide (40 ml) was cooled in an ice bath and stirred as sodium hydride (60% dispersion in mineral oil) (0.66 g, 16.5 mmole) was added in portions over 10 minutes. The mixture was stirred for a further 30 minutes, then a solution of 3-[2-(E)-quinolin-2-yl ethenyl]benzyl chloride (Example 1b) (4.24 g, 15.2 mmole) in dry THF (12 ml) was added over 2 minutes. The reaction mixture was stirred at room temperature for 3 days, then poured into water, extracted into ethyl acetate, dried and evaporated. The residue was chromatographed on silica, eluting with ethyl acetate-hexane (1:3) to give the product.

Workup

  1. additionwas added in portions over 10 minutes
  2. stirringThe reaction mixture was stirred at room temperature for 3 days
  3. extractionextracted into ethyl acetate
  4. customdried
  5. customevaporated
  6. customThe residue was chromatographed on silica
  7. washeluting with ethyl acetate-hexane (1:3)
  8. customto give the product

Sources & evidence

ORD record
ord-fca421f16a0344f6ac053f5e74ab3c34
Source dataset
uspto-grants-1994_01
Patent number
US05281593

Reaction notes

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