5-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine → 4'-(2-Aminopyrimidin-5-yl)-N-ethyl-3'-fluoro-4-(trifluoromethyl)biphenyl-2-sulfonamide
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][CH3:17])(=[O:14])=[O:13].[F:18][C:19]1[CH:24]=[C:23](B2OC(C)(C)C(C)(C)O2)[CH:22]=[CH:21][C:20]=1[C:34]1[CH:35]=[N:36][C:37]([NH2:40])=[N:38][CH:39]=1>>[NH2:40][C:37]1[N:38]=[CH:39][C:34]([C:20]2[CH:21]=[CH:22][C:23]([C:2]3[C:3]([S:12]([NH:15][CH2:16][CH3:17])(=[O:14])=[O:13])=[CH:4][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:7]=3)=[CH:24][C:19]=2[F:18])=[CH:35][N:36]=1Participants
3
Procedure
The title compound was prepared in a manner similar to that described in Example 88 using 2-bromo-N-ethyl-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 C19H16F4N4O2S, 440.09; m/z found, 441.0 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 8.56-8.53 (d, J=1.4, 2H), 8.34-8.31 (m, 1H), 7.99-7.95 (m, 1H), 7.63-7.59 (d, J=8.0, 1H), 7.59-7.53 (m, 1H), 7.36-7.34 (dd, J=7.1, 1.6, 1H), 7.34-7.32 (m, 1H), 2.97-2.71 (q, J=7.2, 2H), 1.15-0.84 (t, J=7.2, 3H).
Sources & evidence
- ORD record
- ord-69ab5d2bff8a4560a12714fb51e52fd4
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079866B2
Reaction notes
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