2-Cyanopyridine-5-boronic acid → (S)-6'-Cyano-2-(3-(hydroxymethyl)pyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)-[3,3'-bipyridine]-5-carboxamide

HRID 923913Notes

Reaction equation

HRID 923913 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].[C:29]([C:31]1[N:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1)#[N:30]>>[C:29]([C:31]1[N:36]=[CH:35][C:34]([C:2]2[C:3]([N:22]3[CH2:26][CH2:25][C@H:24]([CH2:27][OH:28])[CH2:23]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:19])[F:18])=[CH:12][CH:11]=3)=[O:8])[CH:21]=2)=[CH:33][CH:32]=1)#[N:30]

Participants

3

Reactant 2

HCID 547588122-Cyanopyridine-5-boronic acidHCID 86702601(S)-5-bromo-6-(3-(hydroxymethyl)pyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 118195340(S)-6'-Cyano-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 86 using (S)-5-bromo-6-(3-(hydroxymethyl)pyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 78.1) and (6-cyanopyridin-3-yl)boronic acid to afford a light green solid. UPLC-MS (condition 1) tR=2.46 min, m/z=484.1 [M+H]+, m/z=482.1 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.47-1.65 (m, 1H) 1.78-1.93 (m, 1H) 2.17-2.29 (m, 1H) 2.96 (dd, J=10.64, 6.97 Hz, 1H) 3.11-3.23 (m, 2H) 3.24-3.40 (m, 3H in HDO) 4.62 (br. s, 1H) 7.35 (d, J=8.31 Hz, 2H) 7.85 (d, J=8.56 Hz, 2H) 8.02-8.17 (m, 3H) 8.79 (d, J=1.22 Hz, 1H) 8.84 (s, 1H) 10.19 (s, 1H).

Workup

  1. customto afford a light green solid

Sources & evidence

ORD record
ord-1892c607308f4b0e9e1bf2660eead035
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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