3-Pyridinylboronic acid → 2-(3-(2-Hydroxypropan-2-yl)azetidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)-[3,3'-bipyridine]-5-carboxamide
Reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:25][CH:24]([C:26]([OH:29])([CH3:28])[CH3:27])[CH2:23]2)=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[N:30]1[CH:35]=[CH:34][CH:33]=[C:32](B(O)O)[CH:31]=1>>[OH:29][C:26]([CH:24]1[CH2:25][N:22]([C:3]2[C:2]([C:32]3[CH:31]=[N:30][CH:35]=[CH:34][CH:33]=3)=[CH:21][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])=[CH:12][CH:11]=3)=[O:8])=[CH:5][N:4]=2)[CH2:23]1)([CH3:28])[CH3:27]Participants
3
Procedure
The title compound was prepared in an analogous fashion to that described in Example 128 using 5-bromo-6-(3-(2-hydroxypropan-2-yl)azetidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 142.1) and pyridin-3-ylboronic acid to afford an off-white powder. HPLC (Condition 4) tR=4.61 min, UPLC-MS (Condition 7) m/z=473.1 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 0.93 (s, 6H) 3.24-3.34 (m, 1H) 3.59 (m, J=8.60 Hz, 4H) 4.36 (s, 1H) 7.33 (d, J=8.60 Hz, 2H) 7.49 (dd, J=7.82, 4.69 Hz, 1H) 7.84 (d, J=8.99 Hz, 3H) 8.00 (d, J=1.95 Hz, 1H) 8.53-8.62 (m, 1H) 8.65 (d, J=1.95 Hz, 1H) 8.74 (d, J=1.96 Hz, 1H) 10.18 (s, 1H).
Workup
- customto afford an off-white powder
Sources & evidence
- ORD record
- ord-ab6791229d7f44248d24f0ff83362be1
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09278981B2
Reaction notes
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