Water → HCID 21459892, compound

HRID 976244Notes

Reaction equation

HRID 976244 reaction equation
CC(C)([O-])C.[K+].[OH:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[N:10]([CH3:19])[C:9]=1[C:20]([O:22][CH3:23])=[O:21].Cl[CH2:25][C:26]#[N:27].O>CS(C)=O>[C:26]([CH2:25][O:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[N:10]([CH3:19])[C:9]=1[C:20]([O:22][CH3:23])=[O:21])#[N:27]

Participants

6

Reactant 4

HCID 962WaterHCID 7856ChloroacetonitrileHCID 23665647Potassium tert-butoxideHCID 54685033HCID 54685033, compound

Product 1

HCID 21459892HCID 21459892, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A suspension of potassium tert-butoxide (3.2 g, 29 mmol) in 60 mL of dimethyl sulfoxide is treated in portions with methyl 3-hydroxy-5-methoxy-1-methyl-1H-indole-2-carboxylate (5.6 g, 24 mmol; Unangst P. C., et al., J. Heterocyclic Chem., 24:811 (1987)). The mixture is stirred for 15 minutes, and chloroacetonitrile (4.8 mL, 5.7 g, 76 mmol) is added dropwise. The mixture is heated at 80° for 90 minutes, cooled, and added to 800 g of ice and water. The precipitated solid is filtered, washed with 10% methanol-water, and recrystallized from aqueous acetonitrile to give 3.9 g (60%) of product, mp 136°-137° C.

Workup

  1. temperatureThe mixture is heated at 80° for 90 minutes
  2. temperaturecooled
  3. filtrationThe precipitated solid is filtered
  4. washwashed with 10% methanol-water
  5. customrecrystallized from aqueous acetonitrile

Sources & evidence

ORD record
ord-852aea4e55a244d6824be5c1c7a80d9f
Source dataset
uspto-grants-1997_03
Patent number
US05612330

Reaction notes

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