Methyl iodide → 1-(4-chlorobenzyl)-4-(2-methoxyethyl)-5-(4-methoxyphenyl)pyridin-2(1H)-one

HRID 1948270Notes

Reaction equation

HRID 1948270 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[C:10]([CH2:21][CH2:22][OH:23])=[CH:9][C:8]2=[O:24])=[CH:4][CH:3]=1.I[CH3:28]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH:10]([CH2:21][CH2:22][O:23][CH3:28])[CH2:9][C:8]2=[O:24])=[CH:25][CH:26]=1.[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[C:10]([CH2:21][CH2:22][O:23][CH3:28])=[CH:9][C:8]2=[O:24])=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 693503681-(4-chlorobenzyl)-4-(2-hydroxyethyl)-5-(4-methoxyphenyl)pyridin-2(1H)-one

Product 2

HCID 589669471-(4-chlorobenzyl)-4-(2-methoxyethyl)-5-(4-methoxyphenyl)pyridin-2(1H)-oneYield 171.4%HCID 694427411-(4-Chlorobenzyl)-4-(2-methoxyethyl)-5-(4-methoxyphenyl)pyridin-2(4H)-one

Procedure

According to Scheme 30 Step 4: The title compound was prepared from 1-(4-chlorobenzyl)-4-(2-hydroxyethyl)-5-(4-methoxyphenyl)pyridin-2(1H)-one (1 eq, 0.14 mmol, 50 mg) and iodomethane (3 eq, 0.41 mmol, 58 mg) according to the procedure described for Example 34 Step 3. The product was further purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 5 g SiO2) using Et2O/pentane 90/10 to afford 1-(4-chlorobenzyl)-4-(2-methoxyethyl)-5-(4-methoxyphenyl)pyridin-2(1H)-one (0.12 mmol, 47 mg, 91%) as a colorless oil.

Workup

  1. customThe product was further purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 5 g SiO2)

Sources & evidence

ORD record
ord-bd47c347013a405faf28101f1efaebf5
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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