Methanol → 3-cyclohexyl-1H-indole-6-carboxylic Acid

HRID 1982917Notes

Reaction equation

HRID 1982917 reaction equation
[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([OH:18])=[O:17])=[CH:13][CH:14]=3)[NH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.CO>C1COCC1>[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([OH:18])=[O:17])=[CH:13][CH:14]=3)[NH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 887MethanolHCID 111840773-(Cyclohex-1-en-1-yl)-1H-indole-6-carboxylic acid

Product 1

HCID 112419893-cyclohexyl-1H-indole-6-carboxylic AcidYield 79.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Cyclohexenyl-1H-indole-6-carboxylic acid (38 g) was added to a Parr bottle, followed by methanol (100 mL) and THF (100 mL). The bottle was flushed with argon and 10% palladium on carbon (1.2 g) was added. The flask was then evacuated and subsequently refilled with H2 to a pressure of 55 psi, and the resultant mixture was shaken for 18 hours at RT. The catalyst was then removed by filtration through celite. Concentration of the filtrate provided the desired product as a pale purple solid (30.6 g, 79%). ESI-MS m/z 244 (MH+).

Workup

  1. customThe bottle was flushed with argon and 10% palladium on carbon (1.2 g)
  2. additionwas added
  3. customThe flask was then evacuated
  4. additionsubsequently refilled with H2 to a pressure of 55 psi
  5. customThe catalyst was then removed by filtration through celite

Sources & evidence

ORD record
ord-99018730d0ed46bdb62efbfc75aad55d
Source dataset
uspto-grants-2009_06
Patent number
US07541351B2

Reaction notes

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