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

HRID 1958068노트

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HRID 1958068 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(C1C([CH2:29][O:30][C:31]2N=NC(I)=CC=2)=C(C)ON=1)CCC.C(=O)([O-])[O-:40].[Na+].[Na+]>CO.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>[CH3:31][O:30][C:29]([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:40]

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 86647344HCID 86647344, 화합물HCID 86647345HCID 86647345, 화합물

생성물 1

HCID 666438716-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid methyl ester수율 36%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 887Methanol용매

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온도
50 °C

실험 절차

A suspension of 3-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-6-chloro-pyridazine and 3-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-6-iodo-pyridazine (˜1:3 mixture, 2.6 g, ˜7.0 mmol) and sodium carbonate (738 mg, 7.0 mmol) in methanol (20 mL) was evacuated and filled with argon five times. 1,1′-Bis(diphenylphosphino)ferrocene (386 mg, 0.7 mmol) and palladium(II) acetate (156 mg, 0.7 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 (760 mg, ˜36%) as an orange solid. MS: m/e=306.1 [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-d4a30fb09bb042f398f2abb73ac628ab
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410104B2

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