5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile → (R)-5'-Cyano-N-(3-fluoro-4-(trifluoromethoxy)phenyl)-2-(3-hydroxypyrrolidin-1-yl)-[3,3'-bipyridine]-5-carboxamide
반응식
Br[C:2]1[C:3]([N:23]2[CH2:27][CH2:26][C@@H:25]([OH:28])[CH2:24]2)=[N:4][CH:5]=[C:6]([CH:22]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[C:12]([F:21])[CH:11]=1)=[O:8].CC1(C)C(C)(C)OB([C:37]2[CH:38]=[N:39][CH:40]=[C:41]([CH:44]=2)[C:42]#[N:43])O1>>[C:42]([C:41]1[CH:44]=[C:37]([C:2]2[C:3]([N:23]3[CH2:27][CH2:26][C@@H:25]([OH:28])[CH2:24]3)=[N:4][CH:5]=[C:6]([C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[C:12]([F:21])[CH:11]=3)=[O:8])[CH:22]=2)[CH:38]=[N:39][CH:40]=1)#[N:43]참가 물질
3
반응물 2
생성물 1
실험 절차
The title compound was prepared in an analogous fashion to that described in Example 151 using (R)-5-bromo-N-(3-fluoro-4-(trifluoromethoxy)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide (Stage 198.1) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile to afford a yellow solid. UPLC-MS (Condition 3) tR=1.05 min, m/z=488.3 [M+H]+, m/z=486.3 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.75 (s, 1H) 1.81-1.92 (m, 1H) 2.87 (d, J=11.25 Hz, 1H) 3.15-3.27 (m, 2H) 3.33-3.44 (m, 1H) 4.21 (br. s, 1H) 4.87 (d, J=3.42 Hz, 1H) 7.51-7.64 (m, 2H) 7.98 (dd, J=13.20, 2.20 Hz, 1H) 8.08 (d, J=2.20 Hz, 1H) 8.40 (t, J=1.96 Hz, 1H) 8.79 (d, J=2.20 Hz, 1H) 8.90 (d, J=1.96 Hz, 1H) 9.03 (d, J=1.96 Hz, 1H) 10.31 (s, 1H).