[5-(3-pyrrolidin-1-yl-propyl)-1H-indol-2-yl]-methanol → 5-(3-pyrrolidin-1-yl-propyl)-1H-indole-2-carbaldehyde

HRID 49060Notes

Reaction equation

HRID 49060 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13]([CH2:18][OH:19])=[CH:12]3)[CH2:5][CH2:4][CH2:3][CH2:2]1>ClCCl.C1(C)C=CC=CC=1.[O-2].[Mn+4].[O-2]>[N:1]1([CH2:6][CH2:7][CH2:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13]([CH:18]=[O:19])=[CH:12]3)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 1

HCID 22042173[5-(3-pyrrolidin-1-yl-propyl)-1H-indol-2-yl]-methanol

Product 1

HCID 220421225-(3-pyrrolidin-1-yl-propyl)-1H-indole-2-carbaldehydeYield 72.6%

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

Manganese (IV) oxide (4.7 g, 54 mmol) was added to a mixture of [5-(3-pyrrolidin-1-yl-propyl)-1H-indol-2-yl]-methanol (940 mg, 3.6 mmol) in dichloromethane (150 mL) and toluene (150 mL). The mixture was stirred at room temperature for overnight. The reaction was filtered through a pad of celite and the filtrate was concentrated to give 670 mg (72%) of 5-(3-pyrrolidin-1-yl-propyl)-1H-indole-2-carbaldehyde.

Workup

  1. filtrationThe reaction was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-853f4baa99d24863b3a950a94c54b118
Source dataset
uspto-grants-2004_03
Patent number
US06706709B2

Reaction notes

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