1H-Indole-2-carboxylic acid, 1-methyl-5-(phenylmethoxy)-, ethyl ester → Ethyl 3-bromo-1-methyl-5-(phenylmethoxy)-1H-indole-2-carboxylate

HRID 21584Notes

Reaction equation

HRID 21584 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:19]([O:21][CH2:22][CH3:23])=[O:20].C1C=C[NH+]=CC=1.[Br:30][Br-]Br>N1C=CC=CC=1>[Br:30][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:6]=2)[N:2]([CH3:1])[C:3]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

3

Reactant 1

HCID 114836801H-Indole-2-carboxylic acid, 1-methyl-5-(phenylmethoxy)-, ethyl ester

Product 1

HCID 15366237Ethyl 3-bromo-1-methyl-5-(phenylmethoxy)-1H-indole-2-carboxylateYield 76%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of ethyl 1-methyl-5-(phenylmethoxy)-1H-indole-2-carboxylate (60.9 g, 197 mmol; Monge Vega A, et al., An. Ouim. 1976;72:267) in 550 mL of pyridine is cooled in ice and treated dropwise with a solution of pyridinium bromide perbromide (67.0 g, 209 mmol) in 200 mL of pyridine. The cooling bath is removed, and the mixture is stirred for 16 hours, then added to 4.0 L of cold water. The precipitated solid is filtered, washed with water, and recrystallized from ethyl acetate-hexane to give 58.4 g (76%) of product; mp 125-127° C.

Workup

  1. customThe cooling bath is removed
  2. additionadded to 4.0 L of cold water
  3. filtrationThe precipitated solid is filtered
  4. washwashed with water
  5. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-4d6bfc25f1c240d4afa3ad89347851df
Source dataset
uspto-grants-1995_06
Patent number
US05424329

Reaction notes

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