3-Iodo-1-methyl-1H-pyrazole → Benzyl 2-(1-methyl-1H-pyrazol-3-yl)acrylate

HRID 887137노트

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HRID 887137 반응식
I[C:2]1[CH:6]=[CH:5][N:4]([CH3:7])[N:3]=1.C([Sn](CCCC)(CCCC)[C:13](=[CH2:24])[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])CCC>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]Cl>[CH3:7][N:4]1[CH:5]=[CH:6][C:2]([C:13](=[CH2:24])[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])=[N:3]1

참가 물질

6

반응물 2

HCID 133340573-Iodo-1-methyl-1H-pyrazoleHCID 66838741Benzyl 2-(tributylstannyl)acrylate

생성물 1

HCID 66839543Benzyl 2-(1-methyl-1H-pyrazol-3-yl)acrylate수율 67.8%

시약·촉매·용매 3

HCID 62652Cuprous chloride촉매HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매2회

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온도
55 °C

실험 절차

To a solution of 0.30 g (1.4 mmol) of 3-iodo-1-methyl-1H-pyrazole in 3 mL of anhydrous THF was added a solution of 0.82 g (1.8 mmol) of benzyl 2-(tributylstannyl)acrylate from step B above in 1 mL of anhydrous THF, 0.18 g (0.15 mmol) of tetrakis(triphenylphosphine)palladium(0) and 0.14 g (1.4 mmol) of copper (I) chloride. The reaction mixture was heated to 55° C. for 12 h, cooled and evaporated to dryness under reduced pressure. The residue was dissolved in 10 mL of a 1:1 mixture of hexane and EtOAc then filtered through a pad of Celite®. The pad was washed with 15 mL of a 1:1 mixture of hexane and EtOAc and the combined filtrates were evaporated to dryness. The crude residue was purified by silica gel chromatography eluting with a 0-80% EtOAc in hexanes gradient to afford the title compound as a colorless oil (0.23 g, 66%). LC-MS: m/z (ES) 265 (M+Na)+.

후처리

  1. temperaturecooled
  2. customevaporated to dryness under reduced pressure
  3. dissolutionThe residue was dissolved in 10 mL of a 1:1 mixture of hexane and EtOAc
  4. filtrationthen filtered through a pad of Celite®
  5. washThe pad was washed with 15 mL of a 1:1 mixture of hexane and EtOAc
  6. customthe combined filtrates were evaporated to dryness
  7. customThe crude residue was purified by silica gel chromatography
  8. washeluting with a 0-80% EtOAc in hexanes gradient

출처 및 근거

ORD 기록
ord-eee636d060f7434b9dec5b404e9b47c6
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247415B2

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