Potassium Acetate → 4-chloro-6-(2-methoxypyridin-4-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridine

HRID 241971Notes

Reaction equation

HRID 241971 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]2[N:9]([CH3:12])[N:10]=[CH:11][C:3]=12.[CH3:13][O:14][C:15]1[CH:20]=[C:19](B(O)O)[CH:18]=[CH:17][N:16]=1.CC([O-])=O.[K+]>C(#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([C:19]2[CH:18]=[CH:17][N:16]=[C:15]([O:14][CH3:13])[CH:20]=2)[N:5]=[C:4]2[N:9]([CH3:12])[N:10]=[CH:11][C:3]=12

Participants

5

Reactant 3

HCID 517044Potassium AcetateHCID 23546919(2-Methoxypyridin-4-yl)boronic acidHCID 580832354,6-dichloro-1-methyl-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 580832394-chloro-6-(2-methoxypyridin-4-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridineYield 51.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

4,6-Dichloro-1-methyl-1H-pyrazolo[3,4-b]pyridine 5 (0.5 g, 4.9 mmol) was dissolved in acetonitrile (8 mL) and 2-methoxypyridine-4-boronic acid (0.4 g) and 1 M KOAc (8 mL) were added in a microwave tube. Nitrogen was bubbled through the solution for 5 minutes. 1,1′-Bis(diphenylphosphino)ferrocenepalladium (II) chloride (1.21 g) was added and the resultant mixture was then heated by microwave at 120° C. for 5 minutes. The reaction mixture was concentrated in vacuo and purified by flash chromatography (30% EtOAc in hexane) to provide 4-chloro-6-(2-methoxypyridin-4-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridine (0.37 g).

Workup

  1. customNitrogen was bubbled through the solution for 5 minutes
  2. addition1,1′-Bis(diphenylphosphino)ferrocenepalladium (II) chloride (1.21 g) was added
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. custompurified by flash chromatography (30% EtOAc in hexane)

Sources & evidence

ORD record
ord-a3293c49556c410280c7edec9a89e509
Source dataset
uspto-grants-2014_02
Patent number
US08653098B2

Reaction notes

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