3,5-Dichlorophenylboronic acid → HCID 178428711, compound

HRID 505409Notes

Reaction equation

HRID 505409 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH2:9][CH2:10][C:11]2[NH:20][C:14]3=[N:15][CH:16]=[C:17](Br)[CH:18]=[C:13]3[N:12]=2)[N:3]=1.[Cl:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[C:26]([Cl:28])[CH:27]=1>O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+]>[Cl:21][C:22]1[CH:23]=[C:24]([C:17]2[CH:18]=[C:13]3[N:12]=[C:11]([CH2:10][CH2:9][C:4]4[N:3]=[C:2]([NH2:1])[CH:7]=[C:6]([CH3:8])[CH:5]=4)[NH:20][C:14]3=[N:15][CH:16]=2)[CH:25]=[C:26]([Cl:28])[CH:27]=1

Participants

5

Reactant 2

HCID 27343313,5-Dichlorophenylboronic acidHCID 178428704HCID 178428704, compound

Product 1

HCID 178428711HCID 178428711, compoundYield 30.9%

Reagents, catalysts & solvents 2

HCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent

Procedure

The title compound is synthesized according to General Procedure A. 100 mg of 2-[2-(2-amino-4-methylpyridin-6-yl)ethyl]-6-bromo-3H-imidazo[4,5-b]pyridine in 5.0 ml dioxane, 903 μl Na2CO3 solution, 65 mg of 3,5-dichlorophenylboronic acid, 13 mg of PdCl2(PCy3)2, 120° C. for 64 h. During extraction with 20 ml of CH2Cl2/H2O the title compound starts precipitating in the organic layer. Subsequently, 37 mg of the pure title compound can be obtained as a colorless powder after filtration and lyophilization from 2.0 ml dioxane and 1.0 ml water. M.p. 224° C. ESI-MS: 398.3, 400.2, 402.3 (MH+; 100%, 65%, 13%). TLC: Rf=0.24 (dichloromethane/methanol 10:1).

Workup

  1. customThe title compound is synthesized
  2. extractionDuring extraction with 20 ml of CH2Cl2/H2O the title compound
  3. customstarts precipitating in the organic layer

Sources & evidence

ORD record
ord-5a336b6f22664a4fbc683e04d3cca55c
Source dataset
uspto-grants-2010_08
Patent number
US07781453B2

Reaction notes

Loading…