(4-Methoxyphenyl)boronic acid → 1-[(4-Chloro-2-fluorophenyl)methyl]-5-(4-methoxyphenyl)-2(1H)-pyridinone

HRID 1948216Notes

Reaction equation

HRID 1948216 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[CH:12]=[C:11](Br)[CH:10]=[CH:9][C:8]2=[O:14])=[C:4]([F:17])[CH:3]=1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1>>[F:17][C:4]1[CH:3]=[C:2]([Cl:1])[CH:16]=[CH:15][C:5]=1[CH2:6][N:7]1[CH:12]=[C:11]([C:23]2[CH:24]=[CH:25][C:20]([O:19][CH3:18])=[CH:21][CH:22]=2)[CH:10]=[CH:9][C:8]1=[O:14]

Participants

3

Reactant 2

HCID 201262(4-Methoxyphenyl)boronic acidHCID 69349998HCID 69349998, compound

Product 1

HCID 115230231-[(4-Chloro-2-fluorophenyl)methyl]-5-(4-methoxyphenyl)-2(1H)-pyridinoneYield 100%

Procedure

According to Scheme 3 Method A: The title compound was prepared from 1-(4-chloro-2-fluorobenzyl)-5-bromopyridin-2(1H)-one (1 eq, 16.4 mmol, 5.20 g, Example 1 Step 2) and 4-methoxyphenylboronic acid (1.5 eq, 25.0 mmol, 3.80 g) according to the procedure described for Example 1 Step 3. The crude product was purified by flash chromatography over silica gel using CH2Cl2/AcOEt 95/5 to 80/20 as eluent to afford 1-(2-fluoro-4-chlorobenzyl)-5-(4-methoxyphenyl)pyridin-2(1H)-one (16.4 mmol, 5.64 g, 100%) as a white solid.

Workup

  1. customThe crude product was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-6f6782915e94407f9255784ea40f233d
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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