2-Iodotoluene → 2-Methyl-N-[3-(1-{[1-(2-methylphenyl)-1H-indol-5-YL]methyl}-4-piperidinyl)phenyl]propanamide

HRID 1832998Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8].[NH:9]1[C:17]2[C:12](=[CH:13][C:14]([CH2:18][N:19]3[CH2:24][CH2:23][CH:22]([C:25]4[CH:26]=[C:27]([NH:31][C:32](=[O:36])[CH:33]([CH3:35])[CH3:34])[CH:28]=[CH:29][CH:30]=4)[CH2:21][CH2:20]3)=[CH:15][CH:16]=2)[CH:11]=[CH:10]1>>[CH3:35][CH:33]([CH3:34])[C:32]([NH:31][C:27]1[CH:28]=[CH:29][CH:30]=[C:25]([CH:22]2[CH2:23][CH2:24][N:19]([CH2:18][C:14]3[CH:13]=[C:12]4[C:17](=[CH:16][CH:15]=3)[N:9]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[CH3:8])[CH:10]=[CH:11]4)[CH2:20][CH2:21]2)[CH:26]=1)=[O:36]

Participants

Reactant 2

HCID 51282-Iodotoluene

HCID 22049334N-{3-[1-(1H-indol-5-ylmethyl)-4-piperidinyl]phenyl)-2-methylpropanamide

Product 1

HCID 220493012-Methyl-N-[3-(1-{[1-(2-methylphenyl)-1H-indol-5-YL]methyl}-4-piperidinyl)phenyl]propanamide

Procedure

Prepared by Procedure C and Scheme Q1, with CuBr in place of Cu, using 1-iodo-2-methylbenzene and N-{3-[1-(1H-indol-5-ylmethyl)-4-piperidinyl]phenyl}-2-methylpropanamide: ESMS m/e: 466.2 (M+H)+.

Sources & evidence

ORD record: ord-7bbccf74e3404dd4ba216f486cc9e91f
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067534B1

Reaction notes

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