Phenylboronic Acid → N-(6-phenyl[1,2,4]triazolo[1,5-a]pyridin-2-yl)nicotinamide

HRID 2382800Notes

Reaction equation

HRID 2382800 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.[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[C:20]1([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:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 66827Phenylboronic AcidHCID 25212519N-(6-bromo[1,2,4]triazolo[1,5-a]pyridin-2-yl)nicotinamide

Product 1

HCID 59437498N-(6-phenyl[1,2,4]triazolo[1,5-a]pyridin-2-yl)nicotinamideYield 56%

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 phenylboronic 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 (42 mg, 56%). HPLC, Rt: 2.26 min. (purity 98.7%).

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-6b6590337b6b406a8dc9f53bf830e0a3
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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