3-Methylsulfonylaminophenylboronic acid → HCID 58966942, compound

HRID 1948192Notes

Reaction equation

HRID 1948192 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5](=[O:13])[N:6]([CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])[CH:7]=1.[CH3:14][S:15]([NH:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1)(=[O:17])=[O:16]>>[CH2:8]([N:6]1[C:5](=[O:13])[CH:4]=[CH:3][C:2]([C:23]2[CH:24]=[C:19]([NH:18][S:15]([CH3:14])(=[O:16])=[O:17])[CH:20]=[CH:21][CH:22]=2)=[CH:7]1)[CH2:9][CH:10]([CH3:12])[CH3:11]

Participants

3

Reactant 2

HCID 27735353-Methylsulfonylaminophenylboronic acidHCID 60746897HCID 60746897, compound

Product 1

HCID 58966942HCID 58966942, compoundYield 78%

Procedure

According to scheme 3 Method A: The title compound was prepared from 5-bromo-1-isopentylpyridin-2(1H)-one (1 eq, 0.41 mmol, 0.10 g) and 3-(methylsulfonamido)phenylboronic acid (1.5 eq, 0.61 mmol, 0.13 g) according to the procedure described for Example 2 Step 2. The crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 15 g SiO2) using CH2Cl2/AcOEt (80/20) as the eluent to afford N-(3-(1-isopentyl-6-oxo-1,6-dihydropyridin-3-yl)phenyl)methanesulfonamide (0.32 mmol, 0.11 g, 77%) as a white solid.

Workup

  1. customThe crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 15 g SiO2)

Sources & evidence

ORD record
ord-0e93bc85458e4a50875dc90259a6f1b7
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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