3,5-Dichlorophenylboronic acid → HCID 178428711, compound

HRID 2250376Notes

Reaction equation

HRID 2250376 reaction equation
NC1[C:7]([CH2:8][CH2:9][C:10]2[NH:19][C:13]3=[N:14][CH:15]=[C:16](Br)[CH:17]=[C:12]3[N:11]=2)=[C:6](C)[CH:5]=[CH:4]N=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:16]2[CH:17]=[C:12]3[N:11]=[C:10]([CH2:9][CH2:8][C:7]4[N:11]=[C:10]([NH2:19])[CH:9]=[C:5]([CH3:4])[CH:6]=4)[NH:19][C:13]3=[N:14][CH:15]=2)[CH:25]=[C:26]([Cl:28])[CH:27]=1

Participants

5

Reactant 2

HCID 27343313,5-Dichlorophenylboronic acidHCID 1784285642-[2-(2-amino-4-methylpyridin-yl)ethyl]-6-bromo-3H-imidazo[4,5-b]pyridine

Product 1

HCID 178428711HCID 178428711, compoundYield 61.7%

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-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-dd67314507b343568cbd4d6d65d9725a
Source dataset
uspto-grants-2008_01
Patent number
US07317021B2

Reaction notes

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