Sodium hydride → 1-benzhydryl-6-chloro-1H-indole-2-carbaldehyde

HRID 1821479Notes

Reaction equation

HRID 1821479 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([CH:11]=[O:12])[NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH:15](Br)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C=O)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[I-]>[CH:15]([N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([Cl:1])[CH:10]=2)[CH:6]=[C:7]1[CH:11]=[O:12])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 236603BromodiphenylmethaneHCID 161151526-Chloro-1H-indole-2-carbaldehyde

Product 1

HCID 161163341-benzhydryl-6-chloro-1H-indole-2-carbaldehydeYield 40%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To 6-chloro-1H-indole-2-carbaldehyde (1 equiv.) in DMF at 0° C. was added NaH (1.25 equiv.) portionwise followed by benzhydryl bromide (1.46 equiv.) and Bu4NI (0.05 equiv.). The mixture was stirred at rt for 42 h before quenching with cold 0.4N HCl at 0° C. After neutralization, the aqueous layer was extracted with ether and the organic layer was washed with cold H2O and dried. Flash chromatography on silica gel gave 1-benzhydryl-6-chloro-1H-indole-2-carbaldehyde in 40% yield.

Workup

  1. custombefore quenching with cold 0.4N HCl at 0° C
  2. extractionAfter neutralization, the aqueous layer was extracted with ether
  3. washthe organic layer was washed with cold H2O
  4. customdried

Sources & evidence

ORD record
ord-c87dc82b287c47e4ab7eb4c8396ac035
Source dataset
uspto-grants-2009_10
Patent number
US07605156B2

Reaction notes

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