(6-Fluoropyridin-3-yl)boronic acid → HCID 118195313, compound

HRID 923865Notes

Reaction equation

HRID 923865 reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:26][CH2:25][C@@H:24]([OH:27])[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:28][C:29]1[N:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1>>[F:28][C:29]1[N:34]=[CH:33][C:32]([C:2]2[C:3]([N:22]3[CH2:26][CH2:25][C@@H:24]([OH:27])[CH2:23]3)=[N:4][CH:5]=[C:6]([C:7]([NH:9][C:10]3[CH:11]=[CH:12][C:13]([O:16][C:17]([F:20])([F:18])[F:19])=[CH:14][CH:15]=3)=[O:8])[CH:21]=2)=[CH:31][CH:30]=1

Participants

3

Reactant 2

HCID 2783397(6-Fluoropyridin-3-yl)boronic acidHCID 86702593(R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 118195313HCID 118195313, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 54 using (R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 35.1) and (6-fluoropyridin-3-yl)boronic acid to afford a white solid. LC-MS (Condition 2) tR=1.91 min, m/z=463.2-464.2 [M+H]+, m/z=461 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.69-1.78 (m, 1H) 1.79-1.89 (m, 1H) 2.89 (d, J=11.49 Hz, 1H) 3.17-3.28 (m, 2H) 3.34-3.44 (m, 1H) 4.20 (s, 1H) 4.85 (s, 1H) 7.29 (dd, J=8.44, 2.57 Hz, 1H) 7.35 (d, J=8.80 Hz, 2H) 7.85 (d, J=9.29 Hz, 2H) 7.98-8.05 (m, 2H) 8.30 (d, J=1.96 Hz, 1H) 8.77 (d, J=2.20 Hz, 1H) 10.16 (s, 1H).

Workup

  1. customto afford a white solid

Sources & evidence

ORD record
ord-ae2d78f266e447ce8a729c7d7eec4ccb
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

Loading…