Potassium Carbonate → 5-Cyanomethoxy-2-methyl-1H-indole-3-carboxylic Acid Benzyl Ester

HRID 966511Notes

Reaction equation

HRID 966511 reaction equation
Br[CH2:2][C:3]#[N:4].[CH3:5][C:6]1[NH:7][C:8]2[C:13]([C:14]=1[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])=[CH:12][C:11]([OH:25])=[CH:10][CH:9]=2.C(=O)([O-])[O-].[K+].[K+].CCCCCC.C(OCC)(=O)C>C(#N)C>[CH2:18]([O:17][C:15]([C:14]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:25][CH2:2][C:3]#[N:4])[CH:12]=2)[NH:7][C:6]=1[CH3:5])=[O:16])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 109239755-Hydroxy-2-methyl-1H-indole-3-carboxylic acid benzyl esterHCID 21226206Ethyl acetate hexane

Product 1

HCID 233938845-Cyanomethoxy-2-methyl-1H-indole-3-carboxylic Acid Benzyl EsterYield 51%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

α-Bromoacetonitrile (0.209 mL, 3.00 mmol, 1.0 eq.) was dissolved in dry acetonitrile (30 mL) and treated with 2-methyl-3-benzyloxycarbonyl-5-hydroxyindole (0.972 g, 3.46 mmol, 1.2 eq.) and potassium carbonate (0.690 g, 5.0 mmol, 1.7 eq.). The reaction was heated to reflux and followed by TLC (hexane/ethyl acetate 3/2). After 6 hours, the reaction was quenched with water and extracted with ethyl acetate. The resulting organic layers were concentrated, taken up in methylene chloride, and filtered. The filtrate was evaporated to afford a brown solid: 0.490 g (51% yield).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. customthe reaction was quenched with water
  4. extractionextracted with ethyl acetate
  5. concentrationThe resulting organic layers were concentrated
  6. filtrationfiltered
  7. customThe filtrate was evaporated
  8. customto afford a brown solid

Sources & evidence

ORD record
ord-2bdbdd4182d74e7489fd491c0af4d5ef
Source dataset
uspto-grants-2005_10
Patent number
US06951848B2

Reaction notes

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