4-Fluoroiodobenzene → HCID 22048933, compound

HRID 1832231Notes

Reaction equation

HRID 1832231 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.[F:45][C:46]1[CH:51]=[CH:50][C:49](I)=[CH:48][CH:47]=1>>[F:45][C:46]1[CH:51]=[CH:50][C:49]([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:48][CH:47]=1

Participants

4

Reactant 3

HCID 96054-FluoroiodobenzeneHCID 9794286N-(4-methylphenyl)indoleHCID 22049334N-{3-[1-(1H-indol-5-ylmethyl)-4-piperidinyl]phenyl)-2-methylpropanamide

Product 1

HCID 22048933HCID 22048933, compoundYield 45%

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-fluoro-4-iodobenzene (44.4 mg, 0.200 mmol) gave the desired product (21 mg, 45%). 1H NMR (400 MHz, CDCl3) δ 7.71–6.60 (m, 14H), 3.69 (s, 2H), 3.19–2.99 (m, 2H), 2.62–2.41 (m, 2H), 2.22–2.07 (m, 2H), 1.94–1.70 (m, 4H), 1.24 (d, 6H, J=6.8 Hz); ESMS m/e: 470.2 (M+H)+.

Sources & evidence

ORD record
ord-0fedb83da6084f22a85ced80ccd1ce07
Source dataset
uspto-grants-2006_06
Patent number
US07067534B1

Reaction notes

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