Ethyl Acetate → tert-butyl N-[7-(2,4-dimethoxy-6-methylphenyl)-2-methoxypyrazolo[1,5-a]pyridin-3-yl]carbamate

HRID 1865029노트

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HRID 1865029 반응식
Br[C:2]1[N:7]2[N:8]=[C:9]([O:19][CH3:20])[C:10]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[C:6]2[CH:5]=[CH:4][CH:3]=1.[CH3:21][C:22]1[C:27](OB(O)O)=[C:26]([O:32][CH3:33])[CH:25]=[C:24]([O:34][CH3:35])[CH:23]=1.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].C(OCC)(=O)C>COCCOC.O>[CH3:35][O:34][C:24]1[CH:25]=[C:26]([O:32][CH3:33])[CH:27]=[C:22]([CH3:21])[C:23]=1[C:2]1[N:7]2[N:8]=[C:9]([O:19][CH3:20])[C:10]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[C:6]2[CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 17749109Barium hydroxide, octahydrateHCID 21984642tert-butyl N-(7-bromo-2-methoxypyrazolo[1,5-a]pyridin-3-yl)carbamateHCID 219847402,4-Dimethoxy-6-methylphenylboric acid

생성물 1

HCID 21984512tert-butyl N-[7-(2,4-dimethoxy-6-methylphenyl)-2-methoxypyrazolo[1,5-a]pyridin-3-yl]carbamate수율 63.4%

시약·촉매·용매 2

HCID 962Water용매2회HCID 80711,2-Dimethoxyethane용매

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온도
80 °C

실험 절차

After dissolving tert-butyl N-(7-bromo-2-methoxypyrazolo[1,5-a]pyridin-3-yl)carbamate (300 mg) in 1,2-dimethoxyethane (10 mL) and water (5 mL), 6-methyl-2,4-dimethoxyphenylboric acid (258 mg), tetrakis (triphenylphosphine)palladium(0) complex (203 mg) and barium hydroxide octahydrate (415 mg) were added and the mixture was heated and stirred at 80° C. for 3 hours. Water was added to the reaction mixture, extraction was performed with ethyl acetate and the extract washed with brine. After drying the obtained organic layer over anhydrous magnesium sulfate and filtering it, the solvent was concentrated under reduced pressure, the residue was purified by silica gel column chromatography, and the title compound (230 mg) was obtained from the n-hexane:ethyl acetate (5:1) fraction as a brown oil.

후처리

  1. additionwere added
  2. temperaturethe mixture was heated
  3. washthe extract washed with brine
  4. dry with materialAfter drying the obtained organic layer over anhydrous magnesium sulfate
  5. filtrationfiltering it
  6. concentrationthe solvent was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-2a711de7fca84702889f9ff597939656
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07625925B2

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