4-Hydroxyphenylboronic acid → N-[6-(4-hydroxyphenyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]benzamide

HRID 2382846Notes

Reaction equation

HRID 2382846 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:8]=[C:9]([NH:11][C:12](=[O:19])[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:10]=2)[CH:7]=1.[OH:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1>>[OH:20][C:21]1[CH:26]=[CH:25][C:24]([C:2]2[CH:3]=[CH:4][C:5]3[N:6]([N:8]=[C:9]([NH:11][C:12](=[O:19])[C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[N:10]=3)[CH:7]=2)=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 27343604-Hydroxyphenylboronic acidHCID 25212517N-(6-bromo[1,2,4]triazolo[1,5-a]pyridin-2-yl)benzamide

Product 1

HCID 25214208N-[6-(4-hydroxyphenyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]benzamide

Procedure

The title compound was prepared following procedure described for example 56 but starting from N-(6-bromo[1,2,4]triazolo[1,5-a]pyridin-2-yl)benzamide ((B5), 150 mg; 0.47 mmol; 1.0 eq.) and 4-hydroxyphenylboronic acid (131 mg; 0.95 mmol; 2.0 eq.) as a white solid (15 mg, 9%). HPLC, Rt: 2.60 min. (purity 97.2%). LC/MS, M+(ESI): 331.1, M−(ESI): 329.1.

Sources & evidence

ORD record
ord-1514ab2f2ea144daacca532dffb81cba
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

Loading…