Potassium Carbonate → HCID 22627363, compound

HRID 278110Notes

Reaction equation

HRID 278110 reaction equation
[C:1]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([C:15]([NH2:17])=[O:16])=[CH:12][CH:13]=2)[NH:8][C:7]=1[CH2:18][CH2:19][CH3:20])(=[O:5])[CH:2]([CH3:4])[CH3:3].[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Br)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][N:8]2[C:9]3[C:14](=[CH:13][CH:12]=[C:11]([C:15]([NH2:17])=[O:16])[CH:10]=3)[C:6]([C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])=[C:7]2[CH2:18][CH2:19][CH3:20])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 22627338HCID 22627338, compound

Product 1

HCID 22627363HCID 22627363, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-isobutyryl-2-propylindole-6-carboxamide (100 mg), 4-chlorobenzyl bromine (113 mg) and potassium carbonate (152 mg) in dimethylformamide (2 ml) was heated at 60° C. or 2 hours, and partitioned between ethyl acetate and water. The organic layer was washed with water and brine, and dried over magnesium sulfate. After evaporation of solvent, the residue was crystallized from a mixture of ethyl acetate and hexane. The crude crystals were recrystallized from a mixture of ethyl acetate and hexane to give 1-(4-chlorobenzyl)-3-isobutyryl-2-propylindole-6-carboxamide (97 mg) as colorless crystals.

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customAfter evaporation of solvent
  5. customthe residue was crystallized from a mixture of ethyl acetate and hexane
  6. customThe crude crystals were recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-677bcd30462f4f91bbc8db1dbc2bfb54
Source dataset
uspto-grants-2002_03
Patent number
US06358992B1

Reaction notes

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