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

HRID 924108Notes

Reaction equation

HRID 924108 reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:26][C@@H:25]([OH:27])[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].[F:29][C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[N:34][CH:35]=1>>[OH:28][C@H:24]1[C@@H:25]([OH:27])[CH2:26][N:22]([C:3]2[C:2]([C:32]3[CH:33]=[N:34][CH:35]=[C:30]([F:29])[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 44717403(5-Fluoropyridin-3-yl)boronic acidHCID 899078595-Bromo-6-((3S,4R)-3,4-dihydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 1181952942-(cis-3,4-Dihydroxypyrrolidin-1-yl)-5'-fluoro-N-(4-(trifluoromethoxy)phenyl)-[3,3'-bipyridine]-5-carboxamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 71 using 5-bromo-6-((3S,4R)-3,4-dihydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 71.1) and 5-fluoropyridin-3-ylboronic acid to afford a brown solid. UPLC-MS (Condition 3) tR=0.92 min, m/z=479.1 [M+H]+, m/z=477.2 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 3.05 (dd, J=10.88, 4.28 Hz, 2H) 3.25 (dd, J=10.64, 5.01 Hz, 2H) 3.92-4.02 (m, 2H) 4.90 (d, J=3.79 Hz, 2H) 7.35 (d, J=8.44 Hz, 2H) 7.80-7.84 (m, 1H) 7.84-7.90 (m, 2H) 8.08 (d, J=2.32 Hz, 1H) 8.47-8.53 (m, 1H) 8.61 (d, J=2.69 Hz, 1H) 8.77 (d, J=2.32 Hz, 1H) 10.19 (s, 1H).

Workup

  1. customto afford a brown solid

Sources & evidence

ORD record
ord-d27fb0488af84271b11fe23146c67a25
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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