Ethyl 5-methoxyindole-2-carboxylate → Ethyl 4-bromo-5-methoxy-1H-indole-2-carboxylate

HRID 515727Notes

Reaction equation

HRID 515727 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6]2.[Br:17]Br>C(O)(=O)C>[Br:17][C:4]1[C:3]([O:2][CH3:1])=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:8]2

Participants

4

Reactant 2

HCID 20926Ethyl 5-methoxyindole-2-carboxylateHCID 24408Bromine

Product 1

HCID 11460715Ethyl 4-bromo-5-methoxy-1H-indole-2-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of ethyl 5-methoxy-1H-indole-2-carboxylate (5 g, 22.81 mmol) in acetic acid (100 mL) was added bromine (1.169 mL, 22.81 mmol) slowly at room temperature. The reaction mixture was stirred at room temperature for 2 days. The solid was filtered off, washed with acetic acid and hexanes, and dried to give the title compound as a white solid (6.8 g). LCMS m/z=298.6 [M+H]+.

Workup

  1. filtrationThe solid was filtered off
  2. washwashed with acetic acid and hexanes
  3. customdried

Sources & evidence

ORD record
ord-44b0e97028664c8189804bdb98e3a482
Source dataset
uspto-grants-2015_08
Patent number
US09108969B2

Reaction notes

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