3-Aminophenylboronic acid → HCID 25213275, compound

HRID 2382810Notes

Reaction equation

HRID 2382810 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.[NH2:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1>>[NH2:20][C:21]1[CH:26]=[C:25]([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:24]=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 922693-Aminophenylboronic acidHCID 25212519N-(6-bromo[1,2,4]triazolo[1,5-a]pyridin-2-yl)nicotinamide

Product 1

HCID 25213275HCID 25213275, compoundYield 40%

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-aminobenzeneboronic acid (64 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 dark red solid (31 mg, 40%). HPLC, Rt: 1.07 min. (purity 96.3%). LC/MS, M+(ESI): 331.4, M−(ESI): 329.4.

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-29ae695c9efd4fba8a5fee7185b08290
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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