Potassium Carbonate → Methyl 6-bromo-1-methyl-1H-indole-3-carboxylate

HRID 1689811Notes

Reaction equation

HRID 1689811 reaction equation
[C:1](=O)(OC)OC.[CH3:7][O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][C:16]([Br:20])=[CH:17][CH:18]=2)[NH:13][CH:12]=1)=[O:10].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:7][O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][C:16]([Br:20])=[CH:17][CH:18]=2)[N:13]([CH3:1])[CH:12]=1)=[O:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12021Dimethyl CarbonateHCID 11499811Methyl 6-Bromo-1H-Indole-3-Carboxylate

Product 1

HCID 57443279Methyl 6-bromo-1-methyl-1H-indole-3-carboxylateYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

Alternate procedure: Add dimethyl carbonate (1.3 L, 12.4 mol) to a mixture of 6-bromo-1H-indole-3-carboxylic acid methyl ester (1.3 kg, 5.1 mol) and potassium carbonate (1.41 kg, 10.2 mol) in DMF (6.0 L) at room temperature. Heat the mixture to 130° C. and stir overnight. Cool the reaction mixture to ˜3° C. and add ice-cold water (6 L). Filter the resulting solid, wash with methanol (2 L) and dry in a vacuum oven to afford 1.1 kg (82%) of the title compound.

Workup

  1. temperatureCool the reaction mixture to ˜3° C.
  2. filtrationFilter the resulting solid
  3. washwash with methanol (2 L)
  4. customdry in a vacuum oven

Sources & evidence

ORD record
ord-b251dc916bf34306afd81533946edd08
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

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