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

HRID 923898Notes

Reaction equation

HRID 923898 reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:26][CH2:25][C@@H:24]([CH2:27][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][CH2:27][C@@H:24]1[CH2:25][CH2:26][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 89906134(R)-5-Bromo-6-(3-(hydroxymethyl)pyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 118195130(R)-2-(3-(Hydroxymethyl)pyrrolidin-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 75 using (R)-5-bromo-6-(3-(hydroxymethyl)pyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 75.1) and pyridin-3-ylboronic acid to afford a white solid. UPLC-MS (condition 1) tR=1.89 min, m/z=459.1-460.1 [M+H]+, m/z=458.2-457.2 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.50-1.61 (m, 1H) 1.79-1.88 (m, 1H) 2.17-2.26 (m, 1H) 2.93-3.00 (m, 1H) 3.10-3.37 (m, 5H) 4.60 (t, J=5.14 Hz, 1H) 7.34 (d, J=8.80 Hz, 2H) 7.48 (dd, J=7.82, 4.89 Hz, 1H) 7.79-7.83 (m, 1H) 7.85 (d, J=9.05 Hz, 2H) 8.03 (d, J=2.20 Hz, 1H) 8.57 (dd, J=4.89, 1.47 Hz, 1H) 8.64 (d, J=2.20 Hz, 1H) 8.76 (d, J=2.20 Hz, 1H) 10.17 (s, 1H).

Workup

  1. customto afford a white solid

Sources & evidence

ORD record
ord-bcdaf29928d745768d06953b39c127d3
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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