Methanol → diethyl 1-(2-cyanoethyl)-1H-indole-2,6-dicarboxylate

HRID 1748264Notes

Reaction equation

HRID 1748264 reaction equation
CO.[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:10]=2)[CH:5]=[C:4]1[C:17]([O:19][CH2:20][CH3:21])=[O:18].[C:22](#[N:25])[CH:23]=[CH2:24].O>O1CCOCC1>[C:22]([CH2:23][CH2:24][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:10]=2)[CH:5]=[C:4]1[C:17]([O:19][CH2:20][CH3:21])=[O:18])#[N:25]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 7855AcrylonitrileHCID 44754779Diethyl 1H-indole-2,6-dicarboxylate2×

Product 1

HCID 67235491diethyl 1-(2-cyanoethyl)-1H-indole-2,6-dicarboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
55 °C

Procedure

A 40% solution of Triton B in methanol (0.50 mL, 1.1 mmol) is added to a suspension of diethyl 1H-indole-2,6-dicarboxylate (Intermediate A, 2.6 g, 10.0 mmol) and acrylonitrile (2.2 mL, 33.4 mmol) in 1,4-dioxane (25 mL). The reaction mixture is warmed to 55° C. for 30 min and then it is stirred at room temperature for 18 h. Water (30 mL) is added and the mixture is extracted with EtOAc. The organic layer is washed with water, brine, dried (Na2SO4) and concentrated to afford the title crude compound (3.0 g, 96%) as a yellow solid which is used in the next step without purification.

Workup

  1. extractionthe mixture is extracted with EtOAc
  2. washThe organic layer is washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-10e21f41970548efb6dba657d9aa025b
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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