N-(3-bromo-4-(2,4-difluorophenoxy)phenyl)ethanesulfonamide → US10023592, Example 279

HRID 575759Notes

Reaction equation

HRID 575759 reaction equation
F[C:2]1[C:3](=[O:18])[N:4]([CH3:17])[CH:5]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:7]=1.Br[C:20]1[CH:21]=[C:22]([NH:35][S:36]([CH3:39])(=[O:38])=[O:37])[CH:23]=[CH:24][C:25]=1[O:26][C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=1[F:34].BrC1C=C(NS(CC)(=O)=O)C=CC=1O[C:48]1[CH:53]=[CH:52]C(F)=CC=1F>>[CH:52]1([C:2]2[C:3](=[O:18])[N:4]([CH3:17])[CH:5]=[C:6]([C:20]3[CH:21]=[C:22]([NH:35][S:36]([CH3:39])(=[O:38])=[O:37])[CH:23]=[CH:24][C:25]=3[O:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=3[F:34])[CH:7]=2)[CH2:53][CH2:48]1

Participants

4

Reactant 3

HCID 117770988N-(3-bromo-4-(2,4-difluorophenoxy)phenyl)ethanesulfonamideHCID 118022469N-[3-bromo-4-(2,4-difluorophenoxy)phenyl]methanesulfonamideHCID 1238237903-Fluoro-1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one

Product 1

HCID 118021466US10023592, Example 279

Procedure

The title compound was prepared in a manner similar to Example 122, substituting 3-cyclopropyl-1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one for 3-Fluoro-1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one and N-[3-bromo-4-(2,4-difluorophenoxy)phenyl]methanesulfonamide for N-[3-Bromo-4-(2,4-difluorophenoxy)phenyl]ethanesulfonamide. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.46-0.54 (m, 2H) 0.77-0.88 (m, 2H) 1.93-2.07 (m, 1H) 2.98-3.05 (m, 3H) 3.44-3.51 (m, 3H) 6.89-6.95 (m, 1H) 7.00-7.12 (m, 3H) 7.13-7.19 (m, 1H) 7.21-7.25 (m, 1H) 7.39-7.48 (m, 1H) 7.71 (s, 1H) 9.56-9.82 (bs, 1H). LCMS (M+H)+=447.

Sources & evidence

ORD record
ord-85d60fe76bce4a9faf8b30c9b606b419
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

Loading…