3-Pyridinylboronic acid → 2-(3-Hydroxy-3-methylazetidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)-[3,3'-bipyridine]-5-carboxamide

HRID 923963Notes

Reaction equation

HRID 923963 reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:25][C:24]([OH:27])([CH3:26])[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:28]1[CH:33]=[CH:32][CH:31]=[C:30](B(O)O)[CH:29]=1>>[OH:27][C:24]1([CH3:26])[CH2:25][N:22]([C:3]2[C:2]([C:30]3[CH:29]=[N:28][CH:33]=[CH:32][CH:31]=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

Participants

3

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 899064985-Bromo-6-(3-hydroxy-3-methylazetidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 1181951552-(3-Hydroxy-3-methylazetidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)-[3,3'-bipyridine]-5-carboxamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 128 using 5-bromo-6-(3-hydroxy-3-methylazetidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 128.1) and pyridin-3-ylboronic acid. HPLC (Condition 4) tR=4.45 min, UPLC-MS (Condition 3) tR=0.95 min, m/z=445.3 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.27 (s, 3H) 3.46-3.61 (m, 4H) 5.43 (s, 1H) 7.33 (d, J=8.99 Hz, 2H) 7.44-7.54 (m, 1H) 7.74-7.90 (m, 3H) 8.02 (d, J=1.95 Hz, 1H) 8.58 (dd, J=4.69, 1.56 Hz, 1H) 8.64 (d, J=2.35 Hz, 1H) 8.75 (d, J=2.35 Hz, 1H) 10.19 (s, 1H).

Sources & evidence

ORD record
ord-292b502240a7477eb1ae310f62da7001
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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