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

HRID 1523892Notes

Reaction equation

HRID 1523892 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][CH2:16][CH2:17][OH:18])(=[O:14])=[O:13].[F:19][C:20]1[CH:25]=[C:24](B2OC(C)(C)C(C)(C)O2)[CH:23]=[CH:22][C:21]=1[C:35]1[CH:36]=[N:37][C:38]([NH2:41])=[N:39][CH:40]=1>>[NH2:41][C:38]1[N:39]=[CH:40][C:35]([C:21]2[CH:22]=[CH:23][C:24]([C:2]3[C:3]([S:12]([NH:15][CH2:16][CH2:17][OH:18])(=[O:14])=[O:13])=[CH:4][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:7]=3)=[CH:25][C:20]=2[F:19])=[CH:36][N:37]=1

Participants

3

Reactant 2

HCID 903127382-Bromo-N-(2-hydroxyethyl)-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 903129614'-(2-Aminopyrimidin-5-yl)-3'-fluoro-N-(2-hydroxyethyl)-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-(2-hydroxyethyl)-5-(trifluoromethyl)benzene-sulfonamide 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 C19H16F4N4O3S, 456.09; m/z found, 457.0 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 8.57-8.53 (d, J=1.4, 2H), 8.38-8.35 (m, 1H), 8.00-7.96 (dd, J=8.1, 1.5, 1H), 7.63-7.60 (d, J=8.0, 1H), 7.59-7.54 (m, 1H), 7.38-7.36 (dd, J=6.1, 1.6, 1H), 7.36-7.34 (m, 1H), 3.51-3.45 (t, J=5.9, 2H), 2.95-2.86 (t, J=5.9, 2H).

Sources & evidence

ORD record
ord-e649f6aea17047419ca9513eaeeb5dc5
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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