(2,3-Dihydro-1-benzofuran-5-yl)boronic acid → N-[6-(2,3-dihydro-1-benzofuran-5-yl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]benzamide

HRID 2382840Notes

Reaction equation

HRID 2382840 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.[O:20]1[C:24]2[CH:25]=[CH:26][C:27](B(O)O)=[CH:28][C:23]=2[CH2:22][CH2:21]1>>[O:20]1[C:24]2[CH:25]=[CH:26][C:27]([C:2]3[CH:3]=[CH:4][C:5]4[N:6]([N:8]=[C:9]([NH:11][C:12](=[O:19])[C:13]5[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=5)[N:10]=4)[CH:7]=3)=[CH:28][C:23]=2[CH2:22][CH2:21]1

Participants

3

Reactant 2

HCID 2773380(2,3-Dihydro-1-benzofuran-5-yl)boronic acidHCID 25212517N-(6-bromo[1,2,4]triazolo[1,5-a]pyridin-2-yl)benzamide

Product 1

HCID 59437443N-[6-(2,3-dihydro-1-benzofuran-5-yl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]benzamideYield 70%

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 2,3-dihydro-1-benzofuran-5-ylboronic acid (155 mg; 0.95 mmol; 2.0 eq.). Purification by flash chromatography on silica (EtOAc/c-Hex, gradient from 40:60 to 100:0) gave the title compound as a white solid (117.2 mg, 69%). HPLC, Rt: 3.18 min. (purity 84.6%). LC/MS, M+(ESI): 357.1, M−(ESI): 355.1.

Workup

  1. customThe title compound was prepared following procedure
  2. customPurification by flash chromatography on silica (EtOAc/c-Hex, gradient from 40:60 to 100:0)

Sources & evidence

ORD record
ord-2aabf307ea404f6f84db409ee67c675a
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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