Potassium Carbonate → HCID 11550771, compound

HRID 907111Notes

Reaction equation

HRID 907111 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([CH:16]=[O:17])=[CH:10][N:11]2[CH2:14][CH3:15])=[CH:7][CH:6]=1)=[O:4].CC1C=CC(S([CH2:28][N+:29]#[C-:30])(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+]>CO>[CH2:14]([N:11]1[C:12]2[C:8](=[CH:7][CH:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:13]=2)[C:9]([C:16]2[O:17][CH:30]=[N:29][CH:28]=2)=[CH:10]1)[CH3:15]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 59425156Methyl 1-ethyl-3-formyl-1H-indole-6-carboxylate

Product 1

HCID 11550771HCID 11550771, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Ethyl-3-formyl-1H-indole-6-carboxylic acid methyl ester (100 mg, 0.42 mmol), TOSMIC (100 mg, 0.52 mmol), K2CO3 (178 mg, 1.29 mmol), and MeOH (800 μL) were heated at 80° C. overnight. The reaction mixture was then partitioned between H2O and ether. After drying and concentrating the organic phase, the product was purified by silica gel chromatography (EtOAc/CH2Cl2, 10/90) to give methyl 1-ethyl-3-oxazol-5-yl-1H-indole-6-carboxylate (26 mg, 23%) as an off-white solid.

Workup

  1. customThe reaction mixture was then partitioned between H2O and ether
  2. customAfter drying
  3. concentrationconcentrating the organic phase
  4. customthe product was purified by silica gel chromatography (EtOAc/CH2Cl2, 10/90)

Sources & evidence

ORD record
ord-4dcb3f1129f447a89eec41371d458b2c
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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