Sodium Cyanide → HCID 67415407, compound

HRID 912748Notes

Reaction equation

HRID 912748 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:7]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([Cl:15])=[CH:10][C:9]=2[CH2:16]Br)=[O:5].[C-:25]#[N:26].[Na+].[Cl-].[NH4+]>CS(C)=O>[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:7]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([Cl:15])=[CH:10][C:9]=2[CH2:16][C:25]#[N:26])=[O:5]

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 67414524HCID 67414524, compound

Product 1

HCID 67415407HCID 67415407, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 1.00 g (2.4 mmol) of 7-bromomethyl-5-chloro-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester in DMSO (10 ml) at RT, 012 g of sodium cyanide was added. The reaction mixture was stirred at RT for one hour, poured on a saturated aqueous ammonium chloride solution and the product was extracted with EtOAc. The combined organic phases were dried over Na2SO4 and concentrated in vacuo. Flash chromatography (SiO2, EtOAc/Hex 9/1) afforded 0.31 g (36%) of 5-chloro-7-cyanomethyl-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester as a light yellow oil.

Workup

  1. extractionthe product was extracted with EtOAc
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1cf3693611ef4af4bb14461dbeacaaf7
Source dataset
uspto-grants-2011_09
Patent number
US08026259B2

Reaction notes

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