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

HRID 2117326

反応式

HRID 2117326 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

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

反応条件

温度
100 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-c15581be39c34d18b9460cca805cbd50
出典データセット
uspto-grants-2008_10
特許番号
US07442701B2

関連ノート

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