HCID 89995372, compound → N-cyclohexyl-6-hydroxy-4-methyl-1H-indole-2-carboxamide

HRID 62662Notes

Reaction equation

HRID 62662 reaction equation
C([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[C:14]([C:18]([NH:20][CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[O:19])[NH:15]2)=[C:11]([CH3:27])[CH:10]=1)C1C=CC=CC=1>C(O)C.[Pd]>[CH:21]1([NH:20][C:18]([C:14]2[NH:15][C:16]3[C:12]([CH:13]=2)=[C:11]([CH3:27])[CH:10]=[C:9]([OH:8])[CH:17]=3)=[O:19])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

4

Reactant 1

HCID 89995372HCID 89995372, compound

Product 1

HCID 89995412N-cyclohexyl-6-hydroxy-4-methyl-1H-indole-2-carboxamideYield 106.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 6-(benzyloxy)-N-cyclohexyl-4-methyl-1H-indole-2-carboxamide (I-9A-a: 1.5 g, 4.14 mmol) in ethanol (30 mL) was added 10% Pd—C (300 mg) and the mixture placed in a Parr hydrogenator (50 psi) at room temperature for 6 h. The reaction mixture was filtered through celite pad and washed with ethanol (30 mL), concentrated under reduced pressure to afford 1.2 g (90%) of N-cyclohexyl-6-hydroxy-4-methyl-1H-indole-2-carboxamide (I-9A-b) as an off-white solid.

Workup

  1. filtrationThe reaction mixture was filtered through celite pad
  2. washwashed with ethanol (30 mL)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d5f9a767edbc4f40815495f349f13dd1
Source dataset
uspto-grants-2016_09
Patent number
US09447039B2

Reaction notes

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