Potassium Carbonate → 4-Benzyl-2-methoxypyridin-3-amine

HRID 2205984Notes

Reaction equation

HRID 2205984 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[NH:9][C:8]=12.IC1C=CC=CC=1.N1CCC[C@H]1C(O)=O.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu]I>[CH2:11]([C:7]1[CH:6]=[CH:5][N:4]=[C:3]([O:2][CH3:1])[C:8]=1[NH2:9])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 145742L-ProlineHCID 1179880467-methoxy-3-phenyl-1H-pyrazolo[3,4-c]pyridine

Product 1

HCID 1179878384-Benzyl-2-methoxypyridin-3-amineYield 69.8%

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 (113 mg), iodobenzene (1.02 g), L-proline (23.0 mg), potassium carbonate (346 mg) and copper(I) iodide (19.1 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 (75 mg).

Workup

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

Sources & evidence

ORD record
ord-88632d28cfc94911a370e3314caacef4
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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