(5-Fluoropyridin-3-yl)boronic acid → (R)-5'-Fluoro-N-(3-fluoro-4-(trifluoromethoxy)phenyl)-2-(3-hydroxypyrrolidin-1-yl)-[3,3'-bipyridine]-5-carboxamide

HRID 924058Notes

Reaction equation

HRID 924058 reaction equation
Br[C:2]1[C:3]([N:23]2[CH2:27][CH2:26][C@@H:25]([OH:28])[CH2:24]2)=[N:4][CH:5]=[C:6]([CH:22]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[C:12]([F:21])[CH:11]=1)=[O:8].[F:29][C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[N:34][CH:35]=1>>[F:29][C:30]1[CH:31]=[C:32]([C:2]2[C:3]([N:23]3[CH2:27][CH2:26][C@@H:25]([OH:28])[CH2:24]3)=[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:18])[F:19])=[C:12]([F:21])[CH:11]=3)=[O:8])[CH:22]=2)[CH:33]=[N:34][CH:35]=1

Participants

3

Reactant 2

HCID 44717403(5-Fluoropyridin-3-yl)boronic acidHCID 86702607(R)-5-bromo-N-(3-fluoro-4-(trifluoromethoxy)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide

Product 1

HCID 118195343(R)-5'-Fluoro-N-(3-fluoro-4-(trifluoromethoxy)phenyl)-2-(3-hydroxypyrrolidin-1-yl)-[3,3'-bipyridine]-5-carboxamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 151 using (R)-5-bromo-N-(3-fluoro-4-(trifluoromethoxy)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide (Stage 198.1) and (5-fluoropyridin-3-yl)boronic acid to afford a yellow wax. UPLC-MS (Condition 3) tR=1.06 min, m/z=481.3 [M+H]+, m/z=479.3 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.70-1.80 (m, 1H) 1.80-1.91 (m, 1H) 2.89 (d, J=11.25 Hz, 1H) 3.19-3.29 (m, 2H) 3.35-3.46 (m, 1H) 4.21 (br. s, 1H) 4.86 (d, J=3.67 Hz, 1H) 7.55 (m, J=8.56 Hz, 1H) 7.61 (m, J=1.47 Hz, 1H) 7.83 (m, J=1.96 Hz, 1H) 7.98 (dd, J=13.20, 2.20 Hz, 1H) 8.07 (d, J=2.20 Hz, 1H) 8.51 (br. s, 1H) 8.60 (d, J=2.69 Hz, 1H) 8.78 (d, J=2.20 Hz, 1H) 10.30 (s, 1H).

Workup

  1. customto afford a yellow wax

Sources & evidence

ORD record
ord-b9ed2870f30c45409fc101593df46efb
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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