Ethanol → 6-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid ethyl ester

HRID 1958075노트

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HRID 1958075 반응식
[CH2:1]([C:5]1[C:9]([CH2:10][O:11][C:12]2[N:13]=[N:14][C:15](Cl)=[CH:16][CH:17]=2)=[C:8]([CH3:19])[O:7][N:6]=1)[CH2:2][CH2:3][CH3:4].[C:20](=[O:23])([O-])[O-:21].[Na+].[Na+].[CH2:26](O)[CH3:27]>C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:26]([O:21][C:20]([C:15]1[N:14]=[N:13][C:12]([O:11][CH2:10][C:9]2[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:6][O:7][C:8]=2[CH3:19])=[CH:17][CH:16]=1)=[O:23])[CH3:27]

참가 물질

6

반응물 3

HCID 702EthanolHCID 10340Sodium CarbonateHCID 86647344HCID 86647344, 화합물

생성물 1

HCID 666439586-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid ethyl ester수율 88%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매

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온도
50 °C

실험 절차

A suspension of 3-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-6-chloro-pyridazine (1.2 g, 3.6 mmol) and sodium carbonate (379 mg, 3.6 mmol) in ethanol (20 mL) was evacuated and filled with argon five times. 1,1′-Bis(diphenylphosphino)ferrocene (198 mg, 3.6 mmol) and palladium(II) acetate (80 mg, 0.36 mmol) were added then the flask was evacuated again and filled with carbon monoxide. The reaction mixture was then heated to 50° C. After 15 h the reaction mixture was cooled, filtered through decalite and evaporated. The residue was purified by chromatography (silica, 0 to 50% ethyl acetate in heptane) to give the title compound (1.0 g, 88%) as a light yellow oil. MS: m/e=320.2 [M+H]+.

후처리

  1. customwas evacuated
  2. additionfilled with argon five times
  3. customthe flask was evacuated again
  4. additionfilled with carbon monoxide
  5. temperatureAfter 15 h the reaction mixture was cooled
  6. filtrationfiltered through decalite
  7. customevaporated
  8. customThe residue was purified by chromatography (silica, 0 to 50% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-0b3fdf0604c04c9b856d069e84307171
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410104B2

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