Benzhydryl-2-methyl-1H-indol-7-yl-ether → 2-methyl-1H-indol-7-ol

HRID 132590Notes

Reaction equation

HRID 132590 reaction equation
C([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[O:23]C2C=CC=C3C=2N(C(C2C=CC=CC=2)C2C=CC=CC=2)C(C)=C3)[CH:16]=[C:15]1[CH3:47])(C1C=CC=CC=1)C1C=CC=CC=1>CO.C1(C)C=CC=CC=1.[OH-].[Pd+2].[OH-]>[CH3:47][C:15]1[NH:14][C:22]2[C:17]([CH:16]=1)=[CH:18][CH:19]=[CH:20][C:21]=2[OH:23]

Participants

5

Reactant 1

HCID 69197050Benzhydryl-2-methyl-1H-indol-7-yl-ether

Product 1

HCID 187652222-methyl-1H-indol-7-olYield 50.1%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

Benzhydryl-2-methyl-1H-indol-7-yl-ether (85 mg, 0.271 mmol) in methanol (MeOH) (3 mL) and toluene (3 mL) was hydrogenated in the presence of 20% palladium hydroxide (Pd(OH)2) (40 mg) at 40 p.s.i for 70 min at room temperature. The catalyst was filtered off, filtrate concentrated and the residue purified by silica gel flash chromatography to give subtitled compound (20 mg).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationfiltrate concentrated
  3. customthe residue purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-3988c418b5d546f7bfa026cb218613d3
Source dataset
uspto-grants-2008_06
Patent number
US07388020B2

Reaction notes

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