1-(Bromomethyl)-4-chlorobenzene → 1-(4-chlorobenzyl)-4-(2-hydroxyethyl)-5-(4-methoxyphenyl)pyridin-2(1H)-one

HRID 1948269Notes

Reaction equation

HRID 1948269 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][OH:11])[C:6]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:5][N:4]=1.Br[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1>>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][N:4]2[CH:5]=[C:6]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[C:7]([CH2:9][CH2:10][OH:11])=[CH:8][C:3]2=[O:2])=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 693450622-(2-Methoxy-5-(4-methoxyphenyl)pyridin-4-yl)ethanol

Product 1

HCID 693503681-(4-chlorobenzyl)-4-(2-hydroxyethyl)-5-(4-methoxyphenyl)pyridin-2(1H)-oneYield 36%

Procedure

According to Scheme 30 Step 3: The title compound was prepared from 2-(2-methoxy-5-(4-methoxyphenyl)pyridin-4-yl)ethanol (1 eq, 0.62 mmol, 0.16 g) and 1-(bromomethyl)-4-chlorobenzene (1.5 eq, 0.93 mmol, 0.19 g) according to the procedure described for Example 6 Step 2. Reaction conditions: 19 hours under 90° C. The crude product was purified by silica gel chromatography (AIT Flashsmart prepacked column 10 g SiO2) using CH2Cl2/MeOH 98/2 as eluent afford 1-(4-chlorobenzyl)-4-(2-hydroxyethyl)-5-(4-methoxyphenyl)pyridin-2(1H)-one (0.22 mmol, 82 mg, 36%) as a pale yellow solid.

Workup

  1. customReaction conditions
  2. custom19 hours
  3. customunder 90° C
  4. customThe crude product was purified by silica gel chromatography (AIT Flashsmart prepacked column 10 g SiO2)

Sources & evidence

ORD record
ord-1d42d1a20e54462e8f170b75d82b48e3
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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