Potassium Carbonate → 5-(Propan-2-yl)-1H-indole

HRID 356018Notes

Reaction equation

HRID 356018 reaction equation
[CH3:1][CH:2]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9](C(=O)C(F)(F)F)[CH:8]=[CH:7]2)[CH3:3].C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:3][CH:2]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)[CH3:1]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 105629375-Isopropyl-1-trifluoroacetylindole

Product 1

HCID 105589185-(Propan-2-yl)-1H-indoleYield 88.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The trifluoroacetyl indole (D16, 0.25 g, 0.99 mmol) was stirred with potassium carbonate (0.20 g, 1.5 mmol) in methanol (7.5 ml) at 550 C for 1.5 h. Solvent was evaporated and the residue was partitioned between water and dichloromethane. The organic extract was dried and evaporated to give the title compound (0.14 g, 86%). NMR (CDCl3) δ: 1.30 (6H, d, J=7), 3.00 (1H, m, J=7), 6.48 (1H, m), 7.01 (1H, m), 7.09 (1H, d, J=8), 7.20 (1H, d, J=8), 7.49 (1H, s), 7.71 (1H, broad).

Workup

  1. customSolvent was evaporated
  2. customthe residue was partitioned between water and dichloromethane
  3. extractionThe organic extract
  4. customwas dried
  5. customevaporated

Sources & evidence

ORD record
ord-82010b4377ef47d98a105abfb41d9c23
Source dataset
uspto-grants-1998_11
Patent number
US05834494

Reaction notes

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