(5-Fluoropyridin-3-yl)boronic acid → HCID 118195377, compound

HRID 923997Notes

Reaction equation

HRID 923997 reaction equation
Br[C:2]1[C:3]([N:22]([CH2:26][CH3:27])[CH2:23][CH2:24][OH:25])=[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[CH:30]=[C:31](B(O)O)[CH:32]=[N:33][CH:34]=1>>[CH2:26]([N:22]([CH2:23][CH2:24][OH:25])[C:3]1[C:2]([C:31]2[CH:32]=[N:33][CH:34]=[C:29]([F:28])[CH:30]=2)=[CH:21][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=2)=[O:8])=[CH:5][N:4]=1)[CH3:27]

Participants

3

Reactant 2

HCID 44717403(5-Fluoropyridin-3-yl)boronic acidHCID 899065775-bromo-6-(ethyl(2-hydroxyethyl)amino)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 118195377HCID 118195377, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 151 using 5-bromo-6-(ethyl(2-hydroxyethyl)amino)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 156.1) and (5-fluoropyridin-3-yl)boronic acid to afford a white solid. UPLC-MS (Condition 3) tR=1.09 min, m/z=465.3 [M+H]+, m/z=463.4 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 0.90 (t, J=7.03 Hz, 3H) 3.16 (q, J=7.03 Hz, 2H) 3.35-3.42 (m, 2H) 3.49 (br. s, 2H) 4.62 (br. s, 1H) 7.36 (d, J=8.41 Hz, 2H) 7.80-7.89 (m, 2H) 7.98 (m, J=2.70, 1.82 Hz, 1H) 8.08 (d, J=2.38 Hz, 1H) 8.60 (d, J=2.76 Hz, 1H) 8.64 (t, J=1.63 Hz, 1H) 8.76 (d, J=2.38 Hz, 1H) 10.26 (s, 1H).

Workup

  1. customto afford a white solid

Sources & evidence

ORD record
ord-59cdb31520ff42ca8b571afa78c92d23
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

Loading…