Methanol → 2-{[4-(2-tert-Butylphenyl)piperazin-1-yl]carbonyl}-1-methyl-1H-indol-5-ol

HRID 534893Notes

Reaction equation

HRID 534893 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[C:13]([C:19]([N:21]1[CH2:26][CH2:25][N:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:23][CH2:22]1)=[O:20])=[CH:12]2)C1C=CC=CC=1.CO>[C].[Pd].O1CCCC1>[C:33]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[N:24]1[CH2:23][CH2:22][N:21]([C:19]([C:13]2[N:14]([CH3:18])[C:15]3[C:11]([CH:12]=2)=[CH:10][C:9]([OH:8])=[CH:17][CH:16]=3)=[O:20])[CH2:26][CH2:25]1)([CH3:36])([CH3:34])[CH3:35]

Participants

5

Reactant 2

HCID 887MethanolHCID 66751174HCID 66751174, compound

Product 1

HCID 667511892-{[4-(2-tert-Butylphenyl)piperazin-1-yl]carbonyl}-1-methyl-1H-indol-5-olYield 80%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-(benzyloxy)-2-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}-1-methyl-1H-indole obtained in Example 26 (830 mg), palladium carbon (contains 50% H2O, 100 mg), methanol (100 mL), and tetrahydrofuran (50 mL) was stirred at room temperature under hydrogen atmosphere (5 atm). The mixture was filtered and evaporated under reduced pressure to provide the title compound (540 mg, 80%) as a solid.

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f64c42b3ab894a1e81faa9fc9d879d87
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

Loading…