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

HRID 1710447Notes

Reaction equation

HRID 1710447 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[C:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:11]=2)=[O:7])[CH3:4].Br[CH2:23][C:24]#[N:25]>CN(C=O)C>[CH2:3]([O:5][C:6]([C:8]1[N:9]([CH2:23][C:24]#[N:25])[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[C:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:11]=2)=[O:7])[CH3:4]

Participants

5

Reactant 3

HCID 11534BromoacetonitrileHCID 24758Sodium hydrideHCID 44754779Diethyl 1H-indole-2,6-dicarboxylate

Product 1

HCID 58767564diethyl 1-(cyanomethyl)-1H-indole-2,6-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 60% NaH in mineral oil (115 mg, 2.9 mmol) and 1H-indole-2,6-dicarboxylic acid diethyl ester (500 mg, 1.9 mmol) in DMF (3 mL) was stirred at room temperature for 0.5 h. Then bromo-acetonitrile in DMF (1 mL) was added and the reaction was warmed to 77° C. and kept at this temperature overnight. The reaction was cooled and quenched with ice water. A large amount of precipitate formed which was filtered and rinsed with water, followed by cold ether. The wet cake was dried in the vacuum oven (50° C.) to give 585 mg of 1-cyanomethyl-1H-indole-2,6-dicarboxylic acid diethyl ester.

Workup

  1. temperaturethe reaction was warmed to 77° C.
  2. customkept at this temperature overnight
  3. temperatureThe reaction was cooled
  4. customquenched with ice water
  5. customA large amount of precipitate formed which
  6. filtrationwas filtered
  7. washrinsed with water
  8. customThe wet cake was dried in the vacuum oven (50° C.)

Sources & evidence

ORD record
ord-8a8bda555c114889991e7aa0b6747193
Source dataset
uspto-grants-2010_09
Patent number
US07790712B2

Reaction notes

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