5-Bromoindole → 5-bromo-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole

HRID 1028411Notes

Reaction equation

HRID 1028411 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[CH3:11][N:12]1[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:15]1[CH2:16][CH2:17][N:12]([CH3:11])[CH2:13][CH:14]=1

Participants

3

Reactant 2

HCID 249055-BromoindoleHCID 740491-Methyl-4-piperidone

Product 1

HCID 149732085-bromo-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole

Procedure

U.S. Pat. No. 5,786,473 describes a reaction of 5-bromoindole with N-methyl-4-piperidone to obtain 5-bromo-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole which is condensed with N-methylvinylsulfonamide to afford N-methyl-2-[3-(1,2,3,6-tertahydro-1-methyl-4-pyridinyl)-1H-indol-5-yl]ethenesulfonamide which is reduced under heterogeneous hydrogenation conditions to obtain naratritpan.

Sources & evidence

ORD record
ord-03f06f98bac24ae2b883bbc0d6543229
Source dataset
uspto-grants-2014_05
Patent number
US08735589B2

Reaction notes

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