Potassium Carbonate → 7-methoxy-3-phenyl-1-(3-thienyl)-1H-pyrazolo[3,4-c]pyridine

HRID 2205986Notes

Reaction equation

HRID 2205986 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[CH:5][CH:6]=[C:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:10][NH:9][C:8]=12.I[C:19]1[CH:23]=[CH:22][S:21][CH:20]=1.N1CCC[C@H]1C(O)=O.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu]I>[CH3:1][O:2][C:3]1[N:4]=[CH:5][CH:6]=[C:7]2[C:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[N:10][N:9]([C:19]3[CH:23]=[CH:22][S:21][CH:20]=3)[C:8]=12

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 663323-IodothiopheneHCID 145742L-ProlineHCID 1179880467-methoxy-3-phenyl-1H-pyrazolo[3,4-c]pyridine

Product 1

HCID 1179879517-methoxy-3-phenyl-1-(3-thienyl)-1H-pyrazolo[3,4-c]pyridineYield 9.3%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 7-methoxy-3-phenyl-1H-pyrazolo[3,4-c]pyridine (225 mg) obtained in Step C of Example 10, 3-iodothiophene (1.05 g), L-proline (46.1 mg), potassium carbonate (691 mg) and copper(I) iodide (38.1 mg) in DMSO (10 mL) was stirred under nitrogen atmosphere at 180° C. for 1 hr. The reaction mixture was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (28.5 mg).

Workup

  1. customThe reaction mixture was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-570f7907048b47b0b99e76bb4701b7d8
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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