Dichloromethane → HCID 68835338, compound

HRID 2112965Notes

Reaction equation

HRID 2112965 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](B(O)O)[CH:2]=1.C([O-])([O-])=O.[Na+].[Na+].Cl[C:17]1[N:22]2[N:23]=[C:24]([NH2:26])[N:25]=[C:21]2[CH:20]=[C:19]([C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)[CH:18]=1.C(Cl)Cl>C1(C)C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:17]2[N:22]3[N:23]=[C:24]([NH2:26])[N:25]=[C:21]3[CH:20]=[C:19]([C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)[CH:18]=2)[CH:2]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 57643138HCID 57643138, compound

Product 1

HCID 68835338HCID 68835338, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-pyridine boronic acid pinacolate ester (500 mg, 2.44 mmol), Na2CO3 (649 mg, 6.12 mmol) and 5-chloro-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine, which may be produced as in Example 1A, (500 mg, 2.04 mmol) in toluene (30 mL), ethanol (15 mL) and water (15 mL) was degassed by purging with N2 for 10 min. [PdCl2(dppf)].CH2Cl2 (56 mg, 0.082 mmol) was added and the mixture was brought to reflux for 36 h. The solvent was evaporated and the residue was extracted into hot EtOH/MeOH, filtered through Celite, and pre-adsorbed onto SiO2. Column chromatography (0-10% MeOH in CH2Cl2) afforded the product 5,7-di-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine as a solid. MS m/z 289 (M+H+).

Workup

  1. customethanol (15 mL) and water (15 mL) was degassed
  2. customby purging with N2 for 10 min. [PdCl2(dppf)]
  3. temperatureto reflux for 36 h
  4. customThe solvent was evaporated
  5. extractionthe residue was extracted into hot EtOH/MeOH
  6. filtrationfiltered through Celite

Sources & evidence

ORD record
ord-212b59ee5cb2437eb4506ca3b6741675
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

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