Potassium Carbonate → diethyl 1-(cyanomethyl)-1H-indole-2,6-dicarboxylate

HRID 1748252Notes

Reaction equation

HRID 1748252 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:8]=2)[CH:3]=[C:2]1[C:15]([O:17][CH2:18][CH3:19])=[O:16].C([O-])([O-])=O.[K+].[K+].Br[CH2:27][C:28]#[N:29]>CN(C=O)C.CCOC(C)=O>[C:28]([CH2:27][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:8]=2)[CH:3]=[C:2]1[C:15]([O:17][CH2:18][CH3:19])=[O:16])#[N:29]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 44754779Diethyl 1H-indole-2,6-dicarboxylate2×

Product 1

HCID 58767564diethyl 1-(cyanomethyl)-1H-indole-2,6-dicarboxylateYield 84.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of diethyl 1H-indole-2,6-dicarboxylate (Intermediate A, 4.0 g, 15.3 mmol) in dry DMF (50 mL) is added K2CO3 (6.3 g, 45.9 mmol). The reaction mixture is stirred under N2 for 30 min. Bromoacetonitrile (2.1 mL, 30.6 mmol) is added and the reaction mixture is heated to 80° C. for 4 h. After cooling, the reaction mixture is taken up in EtOAc (300 mL) and washed with water, then brine, dried (Na2SO4) and concentrated. The residue is recrystallized from ethanol to afford the title compound (3.9 g, 84%) as fine off-white needles.

Workup

  1. temperatureAfter cooling
  2. washwashed with water
  3. dry with materialbrine, dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-9a3a139b627f4532b5db0026244479b1
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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