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Cesium carbonate → 5-tert-butoxycarbonylmethoxy-1H-indole-2-carboxylic acid ethyl ester

HRID 49047
Notes
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Reaction equation

HRID 49047 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([OH:15])=[CH:10][CH:9]=2)=[O:5])[CH3:2].Br[CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:10][CH:9]=2)=[O:5])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 90677Ethyl 5-hydroxy-1H-indole-2-carboxylate

Product 1

HCID 695874395-tert-butoxycarbonylmethoxy-1H-indole-2-carboxylic acid ethyl esterYield 63%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent
HCID 8857
Ethyl Acetate
Solvent

Procedure

A mixture of 5-hydroxy-1H-indole-2-carboxylic acid ethyl ester (2 g, 10 mmol), tert-butyl bromoacetate (2.35 g, 12 mmol) and cesium carbonate (10.5 g, 30 mmol) in dimethylformamide (10 mL) was stirred at room temperature for 16 hours. The reaction was diluted with ethyl acetate (150 mL), washed with water (5×50 mL) and brine, dried and concentrated. The residue was recrystallized from ethyl acetate and hexane to give 2 g (63%) 5-tert-butoxycarbonylmethoxy-1H-indole-2-carboxylic acid ethyl ester.

Workup

  1. washwashed with water (5×50 mL) and brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-2164c929345b4daca0809a4439a86791
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06706709B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes