Furan-3-boronic acid → N-[6-(3-furyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide

HRID 2382801Notes

Reaction equation

HRID 2382801 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]=[N:15][CH:14]=3)[N:10]=2)[CH:7]=1.[O:20]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21]1>>[O:20]1[CH:24]=[CH:23][C:22]([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]=[N:15][CH:14]=4)[N:10]=3)[CH:7]=2)=[CH:21]1

Participants

3

Reactant 2

HCID 2734358Furan-3-boronic acidHCID 25212519N-(6-bromo[1,2,4]triazolo[1,5-a]pyridin-2-yl)nicotinamide

Product 1

HCID 59437564N-[6-(3-furyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamideYield 21.3%

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)nicotinamide ((B6), 75 mg; 0.24 mmol; 1.0 eq.) and furan-3-boronic acid (57 mg; 0.47 mmol; 2.0 eq.). Purification by flash chromatography on silica (MeOH/EtOAc, 5:95) gave the title compound as a beige powder (15.6 mg, 21%). HPLC, Rt: 1.82 min. (purity 92.2%). LC/MS, M+(ESI): 306.3, M−(ESI): 304.3.

Workup

  1. customThe title compound was prepared following procedure
  2. customPurification by flash chromatography on silica (MeOH/EtOAc, 5:95)

Sources & evidence

ORD record
ord-2331fdc0b7014a4ca3380deb4b498925
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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