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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 923899Generated: October 31, 2026

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

https://huagongshe.com/reaction/923899

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2-Methylpyridine-5-boronic acidHCID 2763081—
Reactant(R)-5-Bromo-6-(3-(hydroxymethyl)pyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamideHCID 89906134—
Product(R)-2-(3-(hydroxymethyl)pyrrolidin-1-yl)-6'-methyl-N-(4-(trifluoromethoxy)phenyl)-[3,3'-bipyridine]-5-carboxamideHCID 118195363—

Reaction Steps

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 (6-methylpyridin-3-yl)boronic acid to afford a white solid. UPLC-MS (condition 1) tR=1.81 min, m/z=473.1-474.1 [M+H]+, m/z=472.2-471.2 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.52-1.61 (m, 1H) 1.78-1.87 (m, 1H) 2.17-2.26 (m, 1H) 2.53 (s, 3H) 2.99 (dd, J=11.00, 6.85 Hz, 1H) 3.11-3.20 (m, 2H) 3.21-3.29 (m, 2H) 3.33-3.37 (m, 1H) 4.60 (t, J=5.14 Hz, 1H) 7.34 (dd, J=8.44, 3.06 Hz, 2H) 7.69 (dd, J=7.82, 2.20 Hz, 1H) 7.85 (d, J=9.05 Hz, 2H) 7.98 (d, J=2.20 Hz, 1H) 8.49 (d, J=1.96 Hz, 1H) 8.74 (d, J=2.20 Hz, 1H) 10.16 (s, 1H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09278981B2
Source datasetuspto-grants-2016_03
ORD IDord-3d7e04a9a9324acf85ce9e0c8aecddaa
Source noteuspto-grants-2016_03