Dimethylformamide → 6-Chloro-1-isopropyl-2-methyl-1H-indole-3-carboxylic acid methyl ester

HRID 250254Notes

Reaction equation

HRID 250254 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[NH:7][C:6]=1[CH3:15])=[O:4].Br[CH:17]([CH3:19])[CH3:18].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[N:7]([CH:17]([CH3:19])[CH3:18])[C:6]=1[CH3:15])=[O:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 57443356methyl 6-chloro-2-methyl-1H-indole-3-carboxylate

Product 1

HCID 672714736-Chloro-1-isopropyl-2-methyl-1H-indole-3-carboxylic acid methyl esterYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-chloro-2-methyl-1H-indole-3-carboxylic acid methyl ester (300 mg, 1.34 mmol), 2-bromopropane (1.75 mL, 18.6 mmol), potassium carbonate (743 mg, 5.37 mmol) and DMF (3.5 mL) is heated to 100° C. for 14 h. The mixture is diluted with water and extracted with ether. The ether layers are washed with water and brine and dried over MgSO4. The residue is purified via flash chromatography eluting with 80% CH2Cl2-heptane to give the title compound (217 mg, 61%) as a white solid. ES/MS m/e 266.0 (M+1).

Workup

  1. extractionextracted with ether
  2. washThe ether layers are washed with water and brine
  3. dry with materialdried over MgSO4
  4. customThe residue is purified via flash chromatography
  5. washeluting with 80% CH2Cl2-heptane

Sources & evidence

ORD record
ord-d6921fcffa254d0e94782db7fe0eecdc
Source dataset
uspto-grants-2011_01
Patent number
US07863302B2

Reaction notes

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