3-Fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → (S)-5'-Fluoro-N-(3-fluoro-4-(trifluoromethoxy)phenyl)-2-(3-(hydroxymethyl)pyrrolidin-1-yl)-[3,3'-bipyridine]-5-carboxamide

HRID 924062Notes

Reaction equation

HRID 924062 reaction equation
Br[C:2]1[C:3]([N:23]2[CH2:27][CH2:26][C@H:25]([CH2:28][OH:29])[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:30][C:31]1[CH:32]=[N:33][CH:34]=[C:35](B2OC(C)(C)C(C)(C)O2)[CH:36]=1>>[F:30][C:31]1[CH:36]=[C:35]([C:2]2[C:3]([N:23]3[CH2:27][CH2:26][C@H:25]([CH2:28][OH:29])[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:18])([F:19])[F:20])=[C:12]([F:21])[CH:11]=3)=[O:8])[CH:22]=2)[CH:34]=[N:33][CH:32]=1

Participants

3

Reactant 2

HCID 164142683-Fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 86702609(S)-5-bromo-N-(3-fluoro-4-(trifluoromethoxy)phenyl)-6-(3-(hydroxymethyl)pyrrolidin-1-yl)nicotinamide

Product 1

HCID 118195144(S)-5'-Fluoro-N-(3-fluoro-4-(trifluoromethoxy)phenyl)-2-(3-(hydroxymethyl)pyrrolidin-1-yl)-[3,3'-bipyridine]-5-carboxamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 185 using (S)-5-bromo-N-(3-fluoro-4-(trifluoromethoxy)phenyl)-6-(3-(hydroxymethyl)pyrrolidin-1-yl)nicotinamide (Stage 201.1) and 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine to afford a white powder. HPLC (Condition 4) tR=5.4 min, UPLC-MS (Condition 3) tR=1.07 min, m/z=495.3 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.46-1.64 (m, 1H) 1.73-1.92 (m, 1H) 2.11-2.27 (m, 1H) 2.85-3.03 (m, 1H) 3.11-3.39 (m, 5H) 4.60 (t, J=1.00 Hz, 1H) 7.41-7.64 (m, 2H) 7.74-7.87 (m, 1H) 7.91-8.00 (m, 1H) 8.04 (d, J=2.35 Hz, 1H) 8.50 (s, 1H) 8.58 (d, J=2.74 Hz, 1H) 8.76 (d, J=1.00 Hz, 1H) 10.29 (s, 1H).

Workup

  1. customto afford a white powder

Sources & evidence

ORD record
ord-39048912159b46d490a235912c253dfb
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

Loading…