N-(3-bromo-4-(2,4-difluorophenoxy)phenyl)ethanesulfonamide → US10023592, Example 281

HRID 518491Notes

Reaction equation

HRID 518491 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:43]([NH:56]S(CC)(=O)=O)[CH:44]=[CH:45][C:46]=1OC1C=CC(F)=CC=1F>>[F:34][C:28]1[CH:29]=[C:30]([F:33])[CH:31]=[CH:32][C:27]=1[O:26][C:25]1[CH:24]=[CH:23][C:22]([NH:35][S:36]([CH3:39])(=[O:38])=[O:37])=[CH:21][C:20]=1[C:6]1[CH:7]=[C:2]([N:56]2[CH2:46][CH2:45][CH2:44][CH2:43]2)[C:3](=[O:18])[N:4]([CH3:17])[CH:5]=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 118022534US10023592, Example 281

Procedure

The title compound was prepared in a manner similar to Example 122, substituting 1-methyl-3-pyrrolidin-1-yl-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-difluorophenoxyl)phenyl]methanesulfonamide for N-[3-Bromo-4-(2,4-difluorophenoxyl)phenyl]ethanesulfonamide. LCMS (M+H)+=476.

Sources & evidence

ORD record
ord-757779ef60574c9eaad2ec366c675fee
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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