3-(1-{[3-(dimethylamino)propyl]sulfonyl}-4-piperidinyl)-5-[3-(hydroxymethyl)phenyl]-1H-indole-7-carboxamide → 3-(1-{[3-(dimethylamino)propyl]sulfonyl}-4-piperidinyl)-5-(3-formylphenyl)-1H-indole-7-carboxamide

HRID 2267502Notes

Reaction equation

HRID 2267502 reaction equation
[CH3:1][N:2]([CH3:35])[CH2:3][CH2:4][CH2:5][S:6]([N:9]1[CH2:14][CH2:13][CH:12]([C:15]2[C:23]3[C:18](=[C:19]([C:32]([NH2:34])=[O:33])[CH:20]=[C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30][OH:31])[CH:25]=4)[CH:22]=3)[NH:17][CH:16]=2)[CH2:11][CH2:10]1)(=[O:8])=[O:7]>C1COCC1.O=[Mn]=O>[CH3:35][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][S:6]([N:9]1[CH2:14][CH2:13][CH:12]([C:15]2[C:23]3[C:18](=[C:19]([C:32]([NH2:34])=[O:33])[CH:20]=[C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]=[O:31])[CH:25]=4)[CH:22]=3)[NH:17][CH:16]=2)[CH2:11][CH2:10]1)(=[O:8])=[O:7]

Participants

4

Reactant 1

HCID 116057133-(1-{[3-(dimethylamino)propyl]sulfonyl}-4-piperidinyl)-5-[3-(hydroxymethyl)phenyl]-1H-indole-7-carboxamide

Product 1

HCID 590033553-(1-{[3-(dimethylamino)propyl]sulfonyl}-4-piperidinyl)-5-(3-formylphenyl)-1H-indole-7-carboxamideYield 65%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(1-{[3-(dimethylamino)propyl]sulfonyl}-4-piperidinyl)-5-[3-(hydroxymethyl)phenyl]-1H-indole-7-carboxamide (230 mg, 0.47 mmol) in THF (60 mL) was added MnO2 (1.3 g, 14.05 mmol). The reaction mixture was stirred at room temperature overnight and filtered through a pad of celite after that. The filtrate was collected and concentrated at reduced pressure to give the crude product (150 mg, 65%), which was used in the next step without further purification.

Workup

  1. filtrationfiltered through a pad of celite after that
  2. customThe filtrate was collected
  3. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-cc62cc7f843041a68530c3cb37189044
Source dataset
uspto-grants-2010_12
Patent number
US07858796B2

Reaction notes

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