Pyridine → methyl 1-phenyl-1H-indazole-3-carboxylate

HRID 2090989Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([O:12][CH3:13])=[O:11])=[N:2]1.[C:14]1(B(O)O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N1C=CC=CC=1>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.CN(C)C=O>[C:14]1([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]([C:10]([O:12][CH3:13])=[O:11])=[N:2]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 30 °C

Procedure

To a mixture of methyl 1H-indazole-3-carboxylate (3.44 g), phenylboronic acid (4.76 g), pyridine (2.84 mL) and N,N-dimethylformamide (70 mL) was added copper (II) acetate (5.32 g), and the mixture was stirred at 30° C. overnight. The insoluble material was filtered off, saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated sodium hydrogen carbonate and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4, volume ratio) to give the title object compound (1.58 g, 32%) as a pale-yellow oil.

Workup

filtrationThe insoluble material was filtered off
additionsaturated aqueous ammonium chloride solution was added
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with saturated sodium hydrogen carbonate and saturated brine
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4, volume ratio)

Sources & evidence

ORD record: ord-20d36dff82c7444e8f19e5d12bb6ec70
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436043B2

Reaction notes

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