Water → HCID 22180676, compound

HRID 1795874Notes

Reaction equation

HRID 1795874 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([NH2:12])=[C:5]2[C:13]#[N:14].[N+:15]([C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH2:21]Br)([O-:17])=[O:16].C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[N+:15]([C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH2:21][O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([NH2:12])=[C:5]2[C:13]#[N:14])([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 22180705HCID 22180705, compound

Product 1

HCID 22180676HCID 22180676, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-hydroxy-2-amino-1-methyl-1H-indole-3-carbonitrile (100 mg; 0.53 mmol) and 3-nitrobenzyl bromide (130 mg; 0.6 mmol) in DMF (5 ml) was treated with Cs2CO3 (520 mg; 1.6 mmol) and the mixture was stirred for 2 hours. Water (80 ml) was added and the precipitate was filtered, taken up in methanol, filtered, washed and dried to give 5-(3-nitrobenzyloxy)-2-amino-1-methyl-1H-indole-3-carbonitrile (96 mg).

Workup

  1. filtrationthe precipitate was filtered
  2. filtrationfiltered
  3. washwashed
  4. customdried

Sources & evidence

ORD record
ord-c2aa5dcabb7c4449bc12f2ac85be93b0
Source dataset
uspto-grants-2006_04
Patent number
US07030123B2

Reaction notes

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