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

HRID 1864993

반응식

HRID 1864993 반응식
[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]

참가 물질

6

반응물 3

HCID 17749109Barium hydroxide, octahydrateHCID 219845347-Bromo-2-ethyl-4-methoxy-3-nitropyrazolo[1,5-a]pyridineHCID 219847594,6-Dimethyl-2-methoxyphenylboric acid

생성물 1

HCID 219847432-Ethyl-4-methoxy-7-(2-methoxy-4,6-dimethylphenyl)-3-nitropyrazolo[1,5-a]pyridine수율 98.3%

시약·촉매·용매 2

HCID 962Water용매2회HCID 12375Ethylene glycol diethyl ether용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-902febfe5f9c416d9859e624697a29c7
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07625925B2

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