5-Bromo-1-[(4-chlorophenyl)methyl]-1,2-dihydropyridin-2-one → HCID 11683170, compound

HRID 1948194Notes

Reaction equation

HRID 1948194 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])=[CH:4][CH:3]=1.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][C:20]=1[NH:28][S:29]([CH3:32])(=[O:31])=[O:30]>>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[C:8](=[O:14])[CH:9]=[CH:10][C:11]([C:22]3[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[C:20]([NH:28][S:29]([CH3:32])(=[O:30])=[O:31])[CH:21]=3)=[CH:12]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 603727735-Bromo-1-[(4-chlorophenyl)methyl]-1,2-dihydropyridin-2-oneHCID 69345138HCID 69345138, compound

Product 1

HCID 11683170HCID 11683170, compoundYield 41%

Procedure

According to Scheme 3 Method A: The title compound was prepared from 1-(4-chlorobenzyl)-5-bromopyridin-2(1H)-one (1 eq, 1.80 mmol, 0.55 g, Example 2 Step 1) and 4-methoxy-3-(methylsulfonamido)phenylboronic acid (1.1 eq, 2.00 mmol, 0.49 g) according to the procedure described for Example 1 Step 3. Reaction conditions: 4 hours at 80° C. The crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 25 g SiO2) using CH2Cl2/AcOEt (90/10) then recrystallized from pentane/Et2O to afford N-(5-(1-(4-chlorobenzyl)-6-oxo-1,6-dihydropyridin-3-yl)-2-methoxyphenyl)methanesulphonamide (0.31 mmol, 0.32 g, 41%) as a white solid.

Workup

  1. customReaction conditions
  2. custom4 hours
  3. customat 80° C
  4. customThe crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 25 g SiO2)
  5. customthen recrystallized from pentane/Et2O

Sources & evidence

ORD record
ord-b11ce2e3bf444ba4a15c51cd548ecdf4
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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