(5-Fluoropyridin-3-yl)boronic acid → 5'-Fluoro-2-((2-hydroxyethyl)(methyl)amino)-N-(4-(trifluoromethoxy)phenyl)-[3,3'-bipyridine]-5-carboxamide

HRID 923993Notes

Reaction equation

HRID 923993 reaction equation
Br[C:2]1[C:3]([N:22]([CH2:24][CH2:25][OH:26])[CH3:23])=[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].[F:27][C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[N:32][CH:33]=1>>[F:27][C:28]1[CH:29]=[C:30]([C:2]2[C:3]([N:22]([CH2:24][CH2:25][OH:26])[CH3:23])=[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])=[CH:12][CH:11]=3)=[O:8])[CH:21]=2)[CH:31]=[N:32][CH:33]=1

Participants

3

Reactant 2

HCID 44717403(5-Fluoropyridin-3-yl)boronic acidHCID 899068275-Bromo-6-((2-hydroxyethyl)(methyl)amino)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 1181953195'-Fluoro-2-((2-hydroxyethyl)(methyl)amino)-N-(4-(trifluoromethoxy)phenyl)-[3,3'-bipyridine]-5-carboxamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 151 using 5-bromo-6-((2-hydroxyethyl)(methyl)amino)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 151.1) and (5-fluoropyridin-3-yl)boronic acid to afford a white solid. UPLC-MS (Condition 3) tR=1.04 min, m/z=451.3 [M+H]+, m/z=449.2 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.71 (s, 3H) 3.44-3.51 (m, 2H) 3.56 (q, J=5.40 Hz, 2H) 4.68 (t, J=5.14 Hz, 1H) 7.36 (d, J=8.41 Hz, 2H) 7.82-7.87 (m, 2H) 7.87-7.93 (m, 1H) 8.12 (d, J=2.38 Hz, 1H) 8.58 (d, J=2.76 Hz, 1H) 8.61 (t, J=1.69 Hz, 1H) 8.75 (d, J=2.38 Hz, 1H) 10.22 (s, 1H).

Workup

  1. customto afford a white solid

Sources & evidence

ORD record
ord-fee4b1f428ba4eeea284f8603ef29daa
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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