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

HRID 1958068ノート

反応式

HRID 1958068 の反応式
[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]

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 86647344HCID 86647344、化合物HCID 86647345HCID 86647345、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-d4a30fb09bb042f398f2abb73ac628ab
出典データセット
uspto-grants-2013_04
特許番号
US08410104B2

反応ノート

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