Barium hydroxide, octahydrate → 2-Ethyl-4-methoxy-7-(2-methoxy-4,6-dimethylphenyl)-3-nitropyrazolo[1,5-a]pyridine

HRID 1864993

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5](OB(O)O)=[C:4]([O:13][CH3:14])[CH:3]=1.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].Br[C:27]1[N:32]2[N:33]=[C:34]([CH2:39][CH3:40])[C:35]([N+:36]([O-:38])=[O:37])=[C:31]2[C:30]([O:41][CH3:42])=[CH:29][CH:28]=1>C(OCCOCC)C.O>[CH2:39]([C:34]1[C:35]([N+:36]([O-:38])=[O:37])=[C:31]2[C:30]([O:41][CH3:42])=[CH:29][CH:28]=[C:27]([C:5]3[C:6]([CH3:8])=[CH:7][C:2]([CH3:1])=[CH:3][C:4]=3[O:13][CH3:14])[N:32]2[N:33]=1)[CH3:40]

Participants

Conditions

Temperature: 80 °C

Procedure

After adding 4,6-dimethyl-2-methoxyphenylboric acid (191 mg), barium hydroxide octahydrate (334 mg) and tetrakis(triphenylphosphine)palladium(0) complex (123 mg) to a solution of 7-bromo-2-ethyl-4-methoxy-3-nitropyrazolo[1,5-a]pyridine (159 mg) in a mixture of ethyleneglycol diethyl ether (15 mL) and water (7.5 mL), the mixture was heated at 80° C. for 30 minutes. Water was added, extraction was performed with ethyl acetate, the extract was washed with saturated aqueous sodium hydrogencarbonate and brine and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (20 g), and the title compound (185 mg) was obtained from the n-hexane:ethyl acetate (5:1) fraction as yellow crystals.

Workup

extractionextraction
washthe extract was washed with saturated aqueous sodium hydrogencarbonate and brine
dry with materialdried over magnesium sulfate
distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-902febfe5f9c416d9859e624697a29c7
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625925B2

Linked notes

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