Cesium carbonate → HCID 21915676, compound

HRID 1245999Notes

Reaction equation

HRID 1245999 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([OH:11])=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:12](=[O:14])[NH2:13].[N+:15]([C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1CBr)([O-:17])=[O:16].[C:26]([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH2:26][C:24]3[CH:23]=[CH:22][CH:19]=[C:18]([N+:15]([O-:17])=[O:16])[CH:25]=3)=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:12](=[O:14])[NH2:13]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 77569alpha-Bromo-2-nitrotolueneHCID 10035419HCID 10035419, compound

Product 1

HCID 21915676HCID 21915676, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1-methyl-2-carbamoyl-5-hydroxy-1H-indole (0.875 g; 4.6 mmol), 2-nitrobenzyl bromide (1 g; 4.63 mmol) and Cs2CO3 (1.5 g; 4.63 mmol) in acetonitrile (55 ml) was heated at 90° C. under argon atmosphere for 2 h 30. After evaporation to dryness, the residue was extracted with CH2Cl2/H2O. The organic phase was evaporated and the residue triturated in CH2Cl2/ether to give 1-methyl-2-carbamoyl-5-(3-nitrobenzyloxy)-1H-indole as a solid.

Workup

  1. customAfter evaporation to dryness
  2. extractionthe residue was extracted with CH2Cl2/H2O
  3. customThe organic phase was evaporated
  4. customthe residue triturated in CH2Cl2/ether

Sources & evidence

ORD record
ord-08681d5529e14b7ca912f8655d8e5a00
Source dataset
uspto-grants-2006_10
Patent number
US07125906B2

Reaction notes

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