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

HRID 923958Notes

Reaction equation

HRID 923958 reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:27][CH2:26][CH2:25][C@H:24]([OH:28])[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:29]1[CH:34]=[CH:33][CH:32]=[C:31](B(O)O)[CH:30]=1>>[OH:28][C@H:24]1[CH2:25][CH2:26][CH2:27][N:22]([C:3]2[C:2]([C:31]3[CH:30]=[N:29][CH:34]=[CH:33][CH:32]=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 89908069HCID 89908069, compound

Product 1

HCID 118195096(S)-2-(3-Hydroxypiperidin-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 118 using (S)-5-bromo-6-(3-hydroxypiperidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 124.1) and pyridin-3-ylboronic acid to afford a white solid. UPLC-MS (condition 1) tR=1.97 min, m/z=459.1 [M+H]+, m/z=457.1 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.19-1.37 (m, 2H) 1.53-1.61 (m, 1H) 1.82 (d, J=8.56 Hz, 1H) 2.58 (dd, J=12.23, 9.05 Hz, 1H) 2.69-2.78 (m, 1H) 3.34-3.40 (m, 1H) 3.41-3.51 (m, 1H) 3.55-3.62 (m, 1H) 4.73 (d, J=4.40 Hz, 1H) 7.36 (d, J=8.56 Hz, 2H) 7.52 (dd, J=7.95, 4.77 Hz, 1H) 7.83-7.89 (m, 2H) 8.02 (dt, J=7.82, 1.83 Hz, 1H) 8.10 (d, J=2.20 Hz, 1H) 8.59 (dd, J=4.65, 1.22 Hz, 1H) 8.76 (d, J=2.20 Hz, 1H) 8.81 (d, J=1.71 Hz, 1H) 10.29 (s, 1H).

Workup

  1. customto afford a white solid

Sources & evidence

ORD record
ord-9b6a55bc7571486ea94a52309e250400
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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