5-Chloropyridine-3-boronic acid → HCID 118195388, compound

HRID 923868Notes

Reaction equation

HRID 923868 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].[Cl:28][C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[N:33][CH:34]=1>>[Cl:28][C:29]1[CH:30]=[C:31]([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:18])([F:19])[F:20])=[CH:14][CH:15]=3)=[O:8])[CH:21]=2)[CH:32]=[N:33][CH:34]=1

Participants

3

Reactant 2

HCID 201118775-Chloropyridine-3-boronic acidHCID 86702593(R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 118195388HCID 118195388, 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 (5-chloropyridin-3-yl)boronic acid to afford a white solid. UPLC-MS (condition 1) tR=2.61 min, m/z=479.1-481.0 [M+H]+, m/z=477.1-479.1 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.70-1.79 (m, 1H) 1.80-1.91 (m, 1H) 2.89 (d, 1H) 3.18-3.28 (m, 2H) 3.35-3.44 (m, 1H) 4.18-4.24 (m, 1H) 4.87 (d, J=3.42 Hz, 1H) 7.35 (d, J=8.80 Hz, 2H) 7.83-7.88 (m, 2H) 8.03 (t, J=1.96 Hz, 1H) 8.08 (d, J=2.20 Hz, 1H) 8.58 (d, J=1.71 Hz, 1H) 8.64 (d, J=2.45 Hz, 1H) 8.78 (d, J=2.45 Hz, 1H) 10.16 (s, 1H).

Workup

  1. customto afford a white solid

Sources & evidence

ORD record
ord-41892c78add8461989587c436591c6a3
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

Loading…