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

HRID 1790902

Reaction equation

HRID 1790902 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].Cl[CH2:17][C:18]([N:20]([CH2:23][CH3:24])[CH2:21][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:19])[N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 16844Chloro-N,N-diethylacetamideHCID 90677Ethyl 5-hydroxy-1H-indole-2-carboxylate

Product 1

HCID 695867965-diethylcarbamoylmethoxy-1H-indole-2-carboxylic acid ethyl esterYield 32.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-hydroxy-1H-indole-2-carboxylic acid ethyl ester (1 g, 5 mmol), 2-chloro-N,N-diethylacetamide (1 mL, 7.5 mmol) and cesium carbonate (5 g, 15 mmol) in dimethylformamide (10 mL) was stirred at room temperature for 6 hours. The reaction was diluted with ethyl acetate (160 mL), washed with water (5×50 mL) and brine, dried and concentrated. The residue was recrystallized from ethyl acetate and hexane to give 0.52 g of 5-diethylcarbamoylmethoxy-1H-indole-2-carboxylic acid ethyl ester as an off-white solid.

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-729e14f27bc94bc7b5b3ec587e691c03
Source dataset
uspto-grants-2006_07
Patent number
US07071332B2

Linked notes

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