Sodium Carbonate → 1-(6-Fluoro-2-pyridyl)-6-(5-isopropenyl-3-pyridyl)pyrazolo[4,3-c]pyridine

HRID 57813

Reaction equation

Cl[C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[N:12]=3)[C:4]=2[CH:3]=1.[C:18]([C:21]1[CH:22]=[N:23][CH:24]=[C:25](B2OC(C)(C)C(C)(C)O2)[CH:26]=1)([CH3:20])=[CH2:19].O.C([O-])(=O)C.[K+].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl>[F:17][C:13]1[N:12]=[C:11]([N:10]2[C:4]3[CH:3]=[C:2]([C:25]4[CH:24]=[N:23][CH:22]=[C:21]([C:18]([CH3:20])=[CH2:19])[CH:26]=4)[N:7]=[CH:6][C:5]=3[CH:8]=[N:9]2)[CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 6-chloro-1-(6-fluoro-2-pyridyl)pyrazolo[4,3-c]pyridine (1.759 mmol; 437.3 mg), 3-isopropenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (2.638 mmol; 646.6 mg), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (0.1759 mmol; 147 mg), potassium acetate hydrate (2.638 mmol; 1.3 mL) and sodium carbonate (2.638 mmol; 1.3 mL) in Acetonitrile (10 mL) in a pressure tube was heated under microwave at 150° C. for 5 min. The mixture was cooled to room temperature. The layers were separated. The aqueous layer was extracted with EtOAc. The combined organic layer was concentrated. The residue was purified on silica eluted with 0 to 6% MeOH in DCM to afford 1-(6-fluoro-2-pyridyl)-6-(5-isopropenyl-3-pyridyl)pyrazolo[4,3-c]pyridine.

Workup

temperatureThe mixture was cooled to room temperature
customThe layers were separated
extractionThe aqueous layer was extracted with EtOAc
concentrationThe combined organic layer was concentrated
customThe residue was purified on silica
washeluted with 0 to 6% MeOH in DCM

Sources & evidence

ORD record: ord-46c1ff7a52d94e9c8438720064bfdcd0
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434725B2

Linked notes

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