HCID 10180234, compound → HCID 10112809, compound

HRID 1781979Notes

Reaction equation

HRID 1781979 reaction equation
[CH3:1][N:2]1[CH2:7][CH:6]=[C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH:17][S:18]([C:21]4[C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[CH:24]=[CH:23][CH:22]=4)(=[O:20])=[O:19])[CH:15]=3)[NH:10][CH:9]=2)[CH2:4][CH2:3]1.[H][H]>CO.[Pd].C(OCC)C>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH:17][S:18]([C:21]4[C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[CH:24]=[CH:23][CH:22]=4)(=[O:20])=[O:19])[CH:15]=3)[NH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 2

HCID 10180234HCID 10180234, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10112809HCID 10112809, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 417 mg (1 mMol) of N-[3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl]naphthalene-1-sulphonamide in 50 ml of methanol are added 100 mg of 5% palladium on carbon. The mixture is hydrogenated at ambient temperature at an initial hydrogen pressure of 3 atmospheres for 20 hours. The reaction mixture is filtered and the filtrate is concentrated at reduced pressure to provide a crude that is suspended in ethyl ether, yielding 272 mg (65%) of N-[3-(1-methyl-piperidin-4-yl)-1H-indol-5-yl]naphthalene-1-sulphonamide as a solid with m.p.=254-256° C.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated at reduced pressure
  3. customto provide a crude that

Sources & evidence

ORD record
ord-89760789d5364662a7531ad6c3dacc80
Source dataset
uspto-grants-2009_03
Patent number
US07498328B2

Reaction notes

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