Dimethylformamide → Indole-5-carboxaldehyde

HRID 1531806Notes

Reaction equation

HRID 1531806 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[H-].[K+].C([Li])(C)(C)C.CN(C)[CH:20]=[O:21]>C(OCC)C>[NH:7]1[C:8]2[C:4](=[CH:3][C:2]([CH:20]=[O:21])=[CH:10][CH:9]=2)[CH:5]=[CH:6]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 249055-BromoindoleHCID 82127Potassium hydrideHCID 178418306HCID 178418306, compound

Product 1

HCID 589040Indole-5-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

5-bromoindole (5.0 g) was added to a stirred suspension of potassium hydride (2.92 g) in diethyl ether (100 ml) at 0° C. The reaction mixture was stirred for 15 mins, cooled to −78° C. before tert-butyl lithium (31.5 ml) was added, and after 30 minutes dimethylformamide (10 ml). The reaction mixture was stirred at room temperature for 18 hrs and then poured into ice-cold 1N HCl the layers were separated and the aqueous was extracted with ethyl acetate (×3). The combined organic layers were washed with saturated sodium bicarbonate solution, brine, dried MgSO4 and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with Dichloromethane/Methanol (97/3, v/v) to afford a white solid (1.8 g).

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred at room temperature for 18 hrs
  3. customwere separated
  4. extractionthe aqueous was extracted with ethyl acetate (×3)
  5. washThe combined organic layers were washed with saturated sodium bicarbonate solution, brine, dried MgSO4
  6. customevaporated under reduced pressure
  7. customThe crude product was purified by column chromatography on silica gel eluting with Dichloromethane/Methanol (97/3

Sources & evidence

ORD record
ord-29eaf71314ed49529c52d2c7f9f6209b
Source dataset
uspto-grants-2001_03
Patent number
US06200978B1

Reaction notes

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