2-Bromo-N-methyl-5-(trifluoromethyl)benzenesulfonamide → 4'-(2-Aminopyrimidin-5-yl)-3'-fluoro-N-methyl-4-(trifluoromethyl)biphenyl-2-sulfonamide

HRID 1523891Notes

Reaction equation

HRID 1523891 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[S:12]([NH:15][CH3:16])(=[O:14])=[O:13].[F:17][C:18]1[CH:23]=[C:22](B2OC(C)(C)C(C)(C)O2)[CH:21]=[CH:20][C:19]=1[C:33]1[CH:34]=[N:35][C:36]([NH2:39])=[N:37][CH:38]=1>>[NH2:39][C:36]1[N:37]=[CH:38][C:33]([C:19]2[CH:20]=[CH:21][C:22]([C:2]3[C:3]([S:12]([NH:15][CH3:16])(=[O:14])=[O:13])=[CH:4][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:7]=3)=[CH:23][C:18]=2[F:17])=[CH:34][N:35]=1

Participants

3

Reactant 2

HCID 903129992-Bromo-N-methyl-5-(trifluoromethyl)benzenesulfonamideHCID 903131425-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine

Product 1

HCID 903126624'-(2-Aminopyrimidin-5-yl)-3'-fluoro-N-methyl-4-(trifluoromethyl)biphenyl-2-sulfonamide

Procedure

The title compound was prepared in a manner similar to that described in Example 88 using 2-bromo-N-methyl-5-(trifluoromethyl)benzenesulfonamide and 5-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine. MS (ESI): mass calcd. for C18H14F4N4O2S, 426.08; m/z found, 427.0 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 8.57-8.52 (d, J=1.4, 2H), 8.33-8.27 (m, 1H), 8.02-7.94 (m, 1H), 7.66-7.60 (d, J=7.9, 1H), 7.60-7.52 (m, 1H), 7.38-7.31 (m, 2H), 2.46 (s, 3H).

Sources & evidence

ORD record
ord-aee845841d8b400eba549411e6a990a4
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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