Ethyl bromoacetate → Ethyl 2-(7-cyano-1H-indol-1-yl)acetate

HRID 453915Notes

Reaction equation

HRID 453915 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10]#[N:11])[CH:3]=[CH:2]1.[H-].[Na+].Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>CN(C=O)C.O>[C:10]([C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[N:1]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:2]=[CH:3]2)#[N:11]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 108988161H-Indole-7-carbonitrile

Product 1

HCID 59473725Ethyl 2-(7-cyano-1H-indol-1-yl)acetateYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1H-indole-7-carbonitrile (2.0 g, 14.08 mmol, 1.0 equiv.) in dry DMF (10 ml) was added at 0° C. to a suspension of NaH (0.845 g, 21.12 mmol, 1.5 equiv. 60% in mineral oil) in DMF (10 ml), and the mixture was stirred for 30 min. Ethyl bromoacetate (1.9 ml, 16.9 mmol, 1.2 equiv.) was added at 0° C., and stirring was carried out for 1 h at RT. When the reaction was complete (TLC monitoring), the mixture was cooled and diluted with water (60 ml). Extraction with ethyl acetate (3×80 ml) was carried out, and the combined organic phases were washed with sat. NaCl solution (2×100 ml), dried over Na2SO4 and concentrated under vacuum. The crude product was purified by column chromatography (silica gel, 8-10% ethyl acetate/hexane) and the desired product was isolated in the form of a yellow solid. Yield: 80% (2.6 g, 11.37 mmol)

Workup

  1. stirringstirring
  2. waitwas carried out for 1 h at RT
  3. temperaturethe mixture was cooled
  4. extractionExtraction with ethyl acetate (3×80 ml)
  5. washthe combined organic phases were washed with sat. NaCl solution (2×100 ml)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under vacuum
  8. customThe crude product was purified by column chromatography (silica gel, 8-10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-70de3662d992443696faa061343a0d7f
Source dataset
uspto-grants-2013_07
Patent number
US08492559B2

Reaction notes

Loading…