HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Methylpyridine-5-boronic acid → (R)-2-(3-(hydroxymethyl)pyrrolidin-1-yl)-6'-methyl-N-(4-(trifluoromethoxy)phenyl)-[3,3'-bipyridine]-5-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Methylpyridine-5-boronic acid | HCID 2763081 | — |
| Reactant | (R)-5-Bromo-6-(3-(hydroxymethyl)pyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide | HCID 89906134 | — |
| Product | (R)-2-(3-(hydroxymethyl)pyrrolidin-1-yl)-6'-methyl-N-(4-(trifluoromethoxy)phenyl)-[3,3'-bipyridine]-5-carboxamide | HCID 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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09278981B2 |
| Source dataset | uspto-grants-2016_03 |
| ORD ID | ord-3d7e04a9a9324acf85ce9e0c8aecddaa |
| Source note | uspto-grants-2016_03 |