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

HRID 9191

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.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[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-b861c7d6b3d849a4a898b1f520c04f67
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091215B2

Linked notes

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