Ethyl Acetate → 7-(2-Chloro-4-methoxyphenyl)-2-ethyl-3-nitropyrazolo[1,5-a]pyridine

HRID 1864987

反応式

HRID 1864987 の反応式
Br[C:2]1[N:7]2[N:8]=[C:9]([CH2:14][CH3:15])[C:10]([N+:11]([O-:13])=[O:12])=[C:6]2[CH:5]=[CH:4][CH:3]=1.[Cl:16][C:17]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:18]=1OB(O)O.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].C(OCC)(=O)C>COCCOC.O>[Cl:16][C:17]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:18]=1[C:2]1[N:7]2[N:8]=[C:9]([CH2:14][CH3:15])[C:10]([N+:11]([O-:13])=[O:12])=[C:6]2[CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 17749109Barium hydroxide, octahydrateHCID 219844817-Bromo-2-ethyl-3-nitropyrazolo[1,5-a]pyridineHCID 219846962-Chloro-4-methoxyphenylboric acid

生成物 1

HCID 219845837-(2-Chloro-4-methoxyphenyl)-2-ethyl-3-nitropyrazolo[1,5-a]pyridine収率 73.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

After dissolving 7-bromo-2-ethyl-3-nitropyrazolo[1,5-a]pyridine (100 mg) in 1,2-dimethoxyethane (6 mL) and water (1 mL), 2-chloro-4-methoxyphenylboric acid (138 mg), tetrakis(triphenylphosphine)palladium(0) complex (86 mg) and barium hydroxide octahydrate (233 mg) were added and the mixture was heated and stirred at 80° C. for 3 hours under a nitrogen stream. Water was added to the reaction mixture, extraction was performed with ethyl acetate and the extract washed with saturated aqueous sodium hydrogencarbonate and brine, in that order. After drying over anhydrous magnesium sulfate and filtration, the solvent was concentrated under reduced pressure, the residue was purified by silica gel column chromatography, and the title compound (90 mg) was obtained from the n-hexane:ethyl acetate (30:1) fraction as yellow crystals.

後処理

  1. additionwere added
  2. temperaturethe mixture was heated
  3. washthe extract washed with saturated aqueous sodium hydrogencarbonate and brine, in that order
  4. dry with materialAfter drying over anhydrous magnesium sulfate and filtration
  5. concentrationthe solvent was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-3577c595748149abaeeb3f032f135b28
出典データセット
uspto-grants-2009_12
特許番号
US07625925B2

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