(3-hydroxyphenyl)boronic Acid → N-[6-(3-hydroxyphenyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]benzamide

HRID 2382833Notes

Reaction equation

HRID 2382833 reaction equation
S1C=CC(C2N3N=C(N)N=C3C=CC=2)=C1.Br[C:17]1[CH:18]=[CH:19][C:20]2[N:21]([N:23]=[C:24]([NH:26][C:27](=[O:34])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:25]=2)[CH:22]=1.[OH:35][C:36]1[CH:37]=[C:38](B(O)O)[CH:39]=[CH:40][CH:41]=1>>[OH:35][C:36]1[CH:41]=[C:40]([C:17]2[CH:18]=[CH:19][C:20]3[N:21]([N:23]=[C:24]([NH:26][C:27](=[O:34])[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[N:25]=3)[CH:22]=2)[CH:39]=[CH:38][CH:37]=1

Participants

4

Reactant 3

HCID 2734359(3-hydroxyphenyl)boronic AcidHCID 25212517N-(6-bromo[1,2,4]triazolo[1,5-a]pyridin-2-yl)benzamideHCID 252159375-(3-Thienyl)[1,2,4]triazolo[1,5-a]pyridin-2-amine

Product 1

HCID 59437437N-[6-(3-hydroxyphenyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]benzamideYield 12%

Procedure

The title compound was prepared following procedure described for intermediate A1, step a), but starting from N-(6-bromo[1,2,4]triazolo[1,5-a]pyridin-2-yl)benzamide ((B5), 75 mg; 0.24 mmol; 1.0 eq.) and 3-hydroxyphenylboronic acid (65 mg; 0.47 mmol; 2.0 eq.). Purification by flash chromatography on silica (EtOAc/c-Hex, gradient from 50:50 to 100:0) gave the title compound as a brown solid (9.5 mg, 12%). HPLC, Rt: 2.59 min. (purity 91.6%). LC/MS, M+(ESI): 331.1, M−(ESI): 329.1.

Workup

  1. customThe title compound was prepared following procedure
  2. customPurification by flash chromatography on silica (EtOAc/c-Hex, gradient from 50:50 to 100:0)

Sources & evidence

ORD record
ord-6d42a4ec4dec46d998b7d308dc760fb4
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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