Sodium Hydroxide → HCID 63749115, compound

HRID 1851891Notes

Reaction equation

HRID 1851891 reaction equation
[Br:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18]C)=[O:17])=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[Br:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([OH:18])=[O:17])=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71074609HCID 71074609, compound

Product 1

HCID 63749115HCID 63749115, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of methyl 1-(4-bromobenzyl)-1H-indole-5-carboxylate (1.09 g, 3.2 mmol, 1 equiv) in methanol (30 mL) was added a 5 N NaOH solution (6.3 mL, 32 mmol, 10 equiv). The reaction mixture was stirred 2 h at 40° C. The mixture was then acidified and extracted with DCM. After concentration in vacuo, the title compound was precipitated in Et2O to afford a white powder (1.03 g, 3.1 mmol, 99%). ESI-MS (m/z): 330/332 [M+H]+.

Workup

  1. extractionextracted with DCM
  2. concentrationAfter concentration in vacuo
  3. customthe title compound was precipitated in Et2O

Sources & evidence

ORD record
ord-74dd180a37064e16ac117a63a6dba131
Source dataset
uspto-grants-2015_02
Patent number
US08957093B2

Reaction notes

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