4-Iodoanisole → N-[3-(1-{[1-(4-Methoxyphenyl)-1H-indol-5-YL]methyl}-4-piperidinyl)phenyl]-2-methylpropanamide

HRID 1832230

Reaction equation

HRID 1832230 reaction equation
CC1C=CC(N2C3C(=CC=CC=3)C=C2)=CC=1.[NH:17]1[C:25]2[C:20](=[CH:21][C:22]([CH2:26][N:27]3[CH2:32][CH2:31][CH:30]([C:33]4[CH:34]=[C:35]([NH:39][C:40](=[O:44])[CH:41]([CH3:43])[CH3:42])[CH:36]=[CH:37][CH:38]=4)[CH2:29][CH2:28]3)=[CH:23][CH:24]=2)[CH:19]=[CH:18]1.I[C:46]1[CH:51]=[CH:50][C:49]([O:52][CH3:53])=[CH:48][CH:47]=1>>[CH3:53][O:52][C:49]1[CH:50]=[CH:51][C:46]([N:17]2[C:25]3[C:20](=[CH:21][C:22]([CH2:26][N:27]4[CH2:32][CH2:31][CH:30]([C:33]5[CH:34]=[C:35]([NH:39][C:40](=[O:44])[CH:41]([CH3:42])[CH3:43])[CH:36]=[CH:37][CH:38]=5)[CH2:29][CH2:28]4)=[CH:23][CH:24]=3)[CH:19]=[CH:18]2)=[CH:47][CH:48]=1

Participants

4

Reactant 3

HCID 696764-IodoanisoleHCID 9794286N-(4-methylphenyl)indoleHCID 22049334N-{3-[1-(1H-indol-5-ylmethyl)-4-piperidinyl]phenyl)-2-methylpropanamide

Product 1

HCID 22049409N-[3-(1-{[1-(4-Methoxyphenyl)-1H-indol-5-YL]methyl}-4-piperidinyl)phenyl]-2-methylpropanamideYield 56.1%

Procedure

According to the procedure used for the synthesis of 1-(4-methylphenyl)1H-indole, N-{3-[1-(1H-indol-5-ylmethyl)-4-piperidinyl]phenyl}-2-methylpropanamide (37.5 mg, 0.100 mmol) and 1-iodo-4-methoxybenzene (46.8 mg, 0.200 mmol) gave the desired product (27 mg, 56%). 1H NMR (400 MHz, CDCl3) δ 7.70–6.58 (m, 14H), 3.88 (s, 3H), 3.67 (s, 2H), 3.14–3.01 (m, 2H), 2.57–2.41 (m, 2H), 2.25–2.01 (m, 2H), 1.93–1.69 (m, 4H), 1.24 (d, 6H, J=7.2 Hz); ESMS m/e: 482.2 (M+H)+.

Sources & evidence

ORD record
ord-a6fd79f82bb248b28b9a25fc8204e6b9
Source dataset
uspto-grants-2006_06
Patent number
US07067534B1

Linked notes

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