3-Methylsulfonylaminophenylboronic acid → N-[3-(1,5-dimethyl-6-oxopyridin-3-yl)phenyl]methanesulfonamide

HRID 575589Notes

Reaction equation

HRID 575589 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:10])[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[CH3:11][S:12]([NH:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1)(=[O:14])=[O:13]>>[CH3:8][N:6]1[C:5](=[O:9])[C:4]([CH3:10])=[CH:3][C:2]([C:20]2[CH:21]=[C:16]([NH:15][S:12]([CH3:11])(=[O:13])=[O:14])[CH:17]=[CH:18][CH:19]=2)=[CH:7]1

Participants

3

Reactant 2

HCID 27735353-Methylsulfonylaminophenylboronic acidHCID 122726645-Bromo-1,3-dimethylpyridin-2(1H)-one

Product 1

HCID 118022363N-[3-(1,5-dimethyl-6-oxopyridin-3-yl)phenyl]methanesulfonamide

Procedure

5-Bromo-1,3-dimethylpyridin-2-one was treated with [3-(methanesulfonamido)phenyl]boronic acid in a manner similar to Example 94 to give the title compound as a white solid. 1H NMR (DMSO-d6, 400 MHz): 9.74 (s, 1H), 7.91 (d, J=2.4 Hz, 1H), 7.62 (s, 1H), 7.37 (t, J=7.6 Hz, 1H), 7.32 (s, 1H), 7.29 (d, J=7.6 Hz, 1H), 7.13 (d, J=7.6 Hz, 1H), 3.52 (s, 3H), 3.02 (s, 3H), 2.08 (s, 3H). LCMS (M+H)+ 293.

Sources & evidence

ORD record
ord-f78b212f9210469ebd9fc5c056a8bf93
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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