Potassium Acetate → N-[3-(1-methyl-6-oxopyridin-3-yl)phenyl]methanesulfonamide

HRID 575586Notes

Reaction equation

HRID 575586 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[CH3:10][S:11]([NH:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1)(=[O:13])=[O:12].CC([O-])=O.[K+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:8][N:6]1[C:5](=[O:9])[CH:4]=[CH:3][C:2]([C:19]2[CH:20]=[C:15]([NH:14][S:11]([CH3:10])(=[O:12])=[O:13])[CH:16]=[CH:17][CH:18]=2)=[CH:7]1

Participants

6

Reactant 3

HCID 517044Potassium AcetateHCID 27735353-Methylsulfonylaminophenylboronic acidHCID 130240275-Bromo-1-methylpyridin-2(1H)-one

Product 1

HCID 118021604N-[3-(1-methyl-6-oxopyridin-3-yl)phenyl]methanesulfonamideYield 20.3%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5-bromo-1-methylpyridin-2-one (100 mg, 0.532 mmol), [3-(methanesulfonamido)phenyl]boronic acid (171.1 mg, 0.798 mmol), KOAc (130.0 mg, 1.326 mmol) and Pd(dppf)Cl2 (38.9 mg, 0.05 mmol) in dioxane/H2O (2 mL/0.5 mL) was stirred at 90° C. for 20 min. The mixture was concentrated and the residue was purified by column chromatography on silica gel (PE:EA=1:1) to give the title compound (30.0 mg, 20%) as a brown solid. 1H NMR (CDCl3, 400 MHz) δ 7.65-7.60 (dd, J1=7.6 Hz, J2=2.4 Hz, 1H), 7.54 (d, J=2.4 Hz, 1H), 7.41 (t, J=8.0 Hz, 1H), 7.33 (s, 1H), 7.24 (d, J=7.6 Hz, 1H), 7.17 (d, J=7.6 Hz, 1H), 6.86 (brs, 1H), 6.67 (d, J=9.2 Hz, 1H), 3.65 (s, 3H), 3.05 (s, 3H). LCMS (M+H)+ 279.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by column chromatography on silica gel (PE:EA=1:1)

Sources & evidence

ORD record
ord-533680c27cc74859b47f88f2fd167f46
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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