3-Cyanophenylboronic acid → HCID 25213276, compound

HRID 2382811Notes

Reaction equation

HRID 2382811 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]([C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1)#[N:21]>>[C:20]([C:22]1[CH:27]=[C:26]([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]=1)#[N:21]

Participants

3

Reactant 2

HCID 27343253-Cyanophenylboronic acidHCID 25212519N-(6-bromo[1,2,4]triazolo[1,5-a]pyridin-2-yl)nicotinamide

Product 1

HCID 25213276HCID 25213276, compoundYield 7.3%

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 3-cyanophenylboronic acid (69 mg; 0.47 mmol; 2.0 eq.). Purification by flash chromatography on silica (MeOH/DCM, gradient from 0:100 to 10:90) gave the title compound as a brown powder (6 mg, 7%). HPLC, Rt: 2.09 min. (purity 92.5%). LC/MS, M+(ESI): 341.4.

Workup

  1. customThe title compound was prepared following procedure
  2. customPurification by flash chromatography on silica (MeOH/DCM, gradient from 0:100 to 10:90)

Sources & evidence

ORD record
ord-a5a7747ffe41464eb3383a887d8deaee
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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