3-Benzyloxy-phenylboronic acid → 6-{2-[6-(3-Benzyloxy-phenyl)-3H-imidazo[4,5-b]pyridin-2-yl]-ethyl}-4-methyl-pyridin-2-ylamine

HRID 2250375Notes

Reaction equation

HRID 2250375 reaction equation
NC1[C:7]([CH2:8][CH2:9][C:10]2[N:18](Br)[C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:12]3[N:11]=2)=[C:6](C)[CH:5]=[CH:4]N=1.[CH2:21]([O:28][C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][CH:34]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+]>[CH2:21]([O:28][C:29]1[CH:30]=[C:31]([C:16]2[CH:17]=[C:12]3[N:11]=[C:10]([CH2:9][CH2:8][C:7]4[N:11]=[C:10]([NH2:18])[CH:9]=[C:5]([CH3:4])[CH:6]=4)[NH:18][C:13]3=[N:14][CH:15]=2)[CH:32]=[CH:33][CH:34]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 27343133-Benzyloxy-phenylboronic acidHCID 691985872-[2-(2-amino-4-methylpyridinyl)ethyl]-bromo-3H-imidazo[4,5-b]pyridine

Product 1

HCID 1784287106-{2-[6-(3-Benzyloxy-phenyl)-3H-imidazo[4,5-b]pyridin-2-yl]-ethyl}-4-methyl-pyridin-2-ylamineYield 122%

Reagents, catalysts & solvents 2

HCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent

Procedure

The title compound is synthesized according to General Procedure A. 150 mg of 2-[2-(2-amino-4-methylpyridinyl)ethyl]-bromo-3H-imidazo[4,5-b]pyridine in 7.5 ml dioxane, 1.36 ml Na2CO3 solution, 116 mg of 3-benzyloxyphenylboronic acid, 20 mg of PdCl2(PCy3)2, 120° C. for 48 h, 20 ml of CH2Cl2/H2O, 220 mg of crude title compound is purified by recrystallization from 6.0 ml isopropyl alcohol to yield 120 mg of the title compound. M.p. 181° C. ESI-MS: 436.3 (MH+). TLC: Rf=0.30 (dichloromethane/methanol 10:1).

Workup

  1. customThe title compound is synthesized
  2. custom20 ml of CH2Cl2/H2O, 220 mg of crude title compound is purified by recrystallization from 6.0 ml isopropyl alcohol

Sources & evidence

ORD record
ord-66d7686582224433abaa57e8da00e135
Source dataset
uspto-grants-2008_01
Patent number
US07317021B2

Reaction notes

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