Sodium Carbonate → 5-(4-tert-Butylphenyl)pyridazin-3(2H)-one

HRID 2117326노트

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HRID 2117326 반응식
Cl[C:2]1[CH:7]=[N:6][NH:5][C:4](=[O:8])[CH:3]=1.[C:9]([C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1)([CH3:12])([CH3:11])[CH3:10].C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O1CCOCC1>[C:9]([C:13]1[CH:18]=[CH:17][C:16]([C:2]2[CH:7]=[N:6][NH:5][C:4](=[O:8])[CH:3]=2)=[CH:15][CH:14]=1)([CH3:12])([CH3:11])[CH3:10]

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 27343204-tert-Butylphenylboronic acidHCID 199057185-Chloropyridazin-3(2H)-one

생성물 1

HCID 691585885-(4-tert-Butylphenyl)pyridazin-3(2H)-one수율 45.9%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

A mixture of 5-chloropyridazin-3(2H)-one (2.94 g, 22.5 mmol), 4-tert-butylphenylboronic acid (8 g, 44.9 mmol), dioxane (100 ml), 2M aqueous sodium carbonate solution (25 ml) and [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium (0.5 g) was degassed (N2), then heated at 100° C. for 18 hours under nitrogen. After cooling to room temperature and standing 24 hours, ethyl acetate (250 ml) was added. The mixture was filtered and the collected solid washed with ethyl acetate to give the title compound 2.36 g. The layers of the filtrate were separated, the aqueous phase extracted with ethyl acetate (100 ml) and the combined organic phases evaporated. Ethyl acetate (100 ml) was added to the residue and the mixture left to stand. A second crop of crystals (2.26 g) was collected and washed with ethyl acetate, giving a combined yield of 4.62 g, 90%.

후처리

  1. customwas degassed (N2)
  2. temperatureAfter cooling to room temperature
  3. additionethyl acetate (250 ml) was added
  4. filtrationThe mixture was filtered
  5. washthe collected solid washed with ethyl acetate

출처 및 근거

ORD 기록
ord-c15581be39c34d18b9460cca805cbd50
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07442701B2

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