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

HRID 241969Notes

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[N:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.CC([O-])=O.[K+]>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[C:6]([C:18]2[CH:19]=[N:20][C:15]([O:14][CH3:13])=[CH:16][CH:17]=2)[N:5]=[C:4]2[N:9]([CH3:12])[N:10]=[CH:11][C:3]=12

Participants

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 1,4-dioxane (8 mL) and 6-methoxypyridin-3-ylboronic acid (0.4 g) and 1 M KOAc (8 mL) were added in a microwave tube. Nitrogen was bubbled through the solution for 1 minute. 1,1′-Bis(diphenylphosphino)ferrocenepalladium (II) chloride (1.2 g) was added and the resultant mixture was 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-(6-methoxypyridin-3-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridine (0.32 g).

Workup

customNitrogen was bubbled through the solution for 1 minute
addition1,1′-Bis(diphenylphosphino)ferrocenepalladium (II) chloride (1.2 g) was added
concentrationThe reaction mixture was concentrated in vacuo
custompurified by flash chromatography (30% EtOAc in hexane)

Sources & evidence

ORD record: ord-d687c3c8a7104f0f9695edd2963bb56b
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653098B2

Reaction notes

Loading…