2-Chloropyridine-5-boronic acid → HCID 118195314, compound

HRID 923910Notes

Reaction equation

HRID 923910 reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:26][CH2:25][C@H:24]([CH2:27][OH:28])[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:29][C:30]1[N:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1>>[Cl:29][C:30]1[N:35]=[CH:34][C:33]([C:2]2[C:3]([N:22]3[CH2:26][CH2:25][C@H:24]([CH2:27][OH:28])[CH2:23]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:19])([F:18])[F:20])=[CH:12][CH:11]=3)=[O:8])[CH:21]=2)=[CH:32][CH:31]=1

Participants

3

Reactant 2

HCID 38450342-Chloropyridine-5-boronic acidHCID 86702601(S)-5-bromo-6-(3-(hydroxymethyl)pyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 118195314HCID 118195314, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 86 using (S)-5-bromo-6-(3-(hydroxymethyl)pyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 78.1) and (6-chloropyridin-3-yl)boronic acid and to afford an off-white solid. UPLC-MS (condition 1) tR=2.51 min, m/z=493.0-495.0 [M+H]+, m/z=494.1-493.1 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.51-1.65 (m, 1H) 1.78-1.92 (m, 1H) 2.23 (ddd, J=13.63, 7.09, 6.91 Hz, 1H) 2.98 (dd, J=10.88, 6.97 Hz, 1H) 3.12-3.22 (m, 2H) 3.21-3.31 (m, 3H, in HDO) 4.62 (br. s, 1H) 7.35 (d, J=8.80 Hz, 2H) 7.61 (d, J=8.31 Hz, 1H) 7.85 (d, J=9.29 Hz, 2H) 7.89 (dd, J=8.31, 2.45 Hz, 1H) 8.03 (d, J=2.44 Hz, 1H) 8.49 (d, J=2.45 Hz, 1H) 8.77 (d, J=2.45 Hz, 1H) 10.17 (s, 1H).

Workup

  1. customto afford an off-white solid

Sources & evidence

ORD record
ord-3ba6a95537874fc6a839339c8e04f8e6
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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