HCID 25210765, compound → HCID 59529905, compound

HRID 1894948Notes

Reaction equation

HRID 1894948 reaction equation
[CH3:1][C:2]([OH:25])([CH3:24])[CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([C:12]2[NH:13][C:14]3[C:19]([CH:20]=2)=[CH:18][C:17]([N+:21]([O-])=O)=[CH:16][CH:15]=3)=[O:11])[CH2:6][CH2:5]1>CO.[C].[Pd]>[NH2:21][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([C:10]([N:7]1[CH2:8][CH2:9][CH:4]([CH2:3][C:2]([CH3:24])([OH:25])[CH3:1])[CH2:5][CH2:6]1)=[O:11])=[CH:20]2

Participants

4

Reactant 1

HCID 25210765HCID 25210765, compound

Product 1

HCID 59529905HCID 59529905, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 838 mg of 2-methyl-1-{1-[(5-nitro-1H-indol-2-yl)carbonyl]piperidin-4-yl}propan-2-ol in 15 mL of methanol was added 80 mg of 10% palladium-carbon, followed by stirring under a hydrogen atmosphere at room temperature for 1 day. Insoluble material was removed by filtration through Celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography [chloroform:methanol=1:0-10:1], and then solidified from hexane-ethyl acetate to obtain 576 mg of 1-{1-[(5-amino-1H-indol-2-yl)carbonyl]piperidin-4-yl}-2-methylpropan-2-ol as a pale brown solid.

Workup

  1. customInsoluble material was removed by filtration through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography [chloroform:methanol=1:0-10:1]

Sources & evidence

ORD record
ord-5aabf934f9804c5e95c25ba02b6fba31
Source dataset
uspto-grants-2013_08
Patent number
US08513422B2

Reaction notes

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