Sodium hydride → HCID 19102593, compound

HRID 1198557Notes

Reaction equation

HRID 1198557 reaction equation
[CH:1]([C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[CH:5][CH:4]=1)=[O:2].[H-].[Na+].[Cl:14][C:15]1[CH:24]=[C:23]2[C:18]([CH:19]=[CH:20][C:21](/[CH:25]=[CH:26]/[C:27]3[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=3)[CH2:30]Cl)=[N:22]2)=[CH:17][CH:16]=1>CN(C=O)C>[Cl:14][C:15]1[CH:24]=[C:23]2[C:18]([CH:19]=[CH:20][C:21](/[CH:25]=[CH:26]/[C:27]3[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=3)[CH2:30][N:9]3[C:10]4[C:6](=[CH:5][CH:4]=[C:3]([CH:1]=[O:2])[CH:11]=4)[CH:7]=[CH:8]3)=[N:22]2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27734351H-Indole-6-carboxaldehydeHCID 19369489trans-3-[2-(7-Chloroquinolin-2-yl)ethenyl]benzyl chloride

Product 1

HCID 19102593HCID 19102593, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-formyl indole (Example 29a) (0.63 g, 4.3 mmol) in dry DMF (20 ml) was added sodium hydride (60% dispersion in oil) (0.22 g, 5.5 mmol) portionwise over 5 minutes with stirring. The reaction mixture was stirred for a further 20 minutes, then solid 3-[2(E)-(7-chloroquinolin-2-yl)ethenyl]benzyl chloride (Example 14b) (1.7 g, 5.4 mmol) was added portionwise over 5 minutes, and the reaction mixture left to stir for 18 hours. The reaction was quenched with water, extracted into ethyl acetate, the combined organic extracts washed with water, then brine, dried, filtered and evaporated in vacuo. The crude solid was purified by flash chromatography on silica, eluting with 30% diethyl ether in hexane to give a pale yellow solid.

Workup

  1. stirringThe reaction mixture was stirred for a further 20 minutes
  2. waitthe reaction mixture left
  3. stirringto stir for 18 hours
  4. customThe reaction was quenched with water
  5. extractionextracted into ethyl acetate
  6. washthe combined organic extracts washed with water
  7. dry with materialbrine, dried
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe crude solid was purified by flash chromatography on silica
  11. washeluting with 30% diethyl ether in hexane
  12. customto give a pale yellow solid

Sources & evidence

ORD record
ord-ae2b0f4508544a908d9b2dcda90c357c
Source dataset
uspto-grants-1994_01
Patent number
US05281593

Reaction notes

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