Water → HCID 22180710, compound

HRID 1795873Notes

Reaction equation

HRID 1795873 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([NH2:18])=[C:12]2[C:19]#[N:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]([O-])([O-])=O.[Cs+].[Cs+].CI.O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:21])[C:13]([NH2:18])=[C:12]2[C:19]#[N:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 22180707HCID 22180707, compound

Product 1

HCID 22180710HCID 22180710, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-benzyloxy-2-amino-1H-indole-3-carbonitrile (2.96 g; 11.25 mmol) in DMF (20 ml) under argon was treated at room temperature with Cs2CO3 (4.4 g; 13.5 mmol). The mixture was stirred and treated dropwise with methyl iodide (0.84 ml; 13.48 mmol). Stirring was continued for 1 hour when the mixture was poured into water. The precipitate was filtered, washed with water and dried to give 5-benzyloxy-2-amino-1-methyl-1H-indole-3-carbonitrile as a beige solid (2.77 g).

Workup

  1. stirringStirring
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-68372f1e2407402dbbe043ba822538bd
Source dataset
uspto-grants-2006_04
Patent number
US07030123B2

Reaction notes

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