Potassium Carbonate → Ethyl 2-(3-methanesulphonylphenyl)thiazole-4-carboxylate

HRID 1695517노트

반응식

HRID 1695517 반응식
Br[C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.[CH3:12][S:13]([C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1)(=[O:15])=[O:14].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C(N1C=CN(C(C)C)C1=[Pd-3](Cl)(Cl)C1C(Cl)=CC=CN=1)(C)C>[CH3:12][S:13]([C:16]1[CH:21]=[C:20]([C:2]2[S:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=2)[CH:19]=[CH:18][CH:17]=1)(=[O:15])=[O:14]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 353965Ethyl 2-bromo-1,3-thiazole-4-carboxylateHCID 27735423-(Methylsulfonyl)phenylboronic acid

생성물 1

HCID 67277205Ethyl 2-(3-methanesulphonylphenyl)thiazole-4-carboxylate수율 47.7%

시약·촉매·용매 2

HCID 178456358HCID 178456358, 화합물촉매HCID 312751,4-Dioxane용매

실험 절차

Ethyl 2-bromothiazole-4-carboxylate (1 g), 3-(methylsulphonyl)phenyl-boronic acid (1.02 g, 1.2 equivalents) and potassium carbonate (1.76 g) are introduced in dioxane (12.5 ml). (1,3-Diisopropylimidazol-2-ylidene)(3-chloropyridyl)palladium(II) dichloride (288 mg) is added, and the mixture is stirred under reflux under protective gas for 18 h. Dioxane is then removed in a rotary evaporator, and the residue is taken up in ethyl acetate and water. The organic phase is separated off and the aqueous phase is back-extracted twice with ethyl acetate. The combined organic phases are washed with brine and dried over sodium sulphate and concentrated. Purification by column chromatography on silica gel (ethyl acetate/hexane) results in a white solid (629 mg).

후처리

  1. temperatureunder reflux under protective gas for 18 h
  2. customDioxane is then removed in a rotary evaporator
  3. customThe organic phase is separated off
  4. extractionthe aqueous phase is back-extracted twice with ethyl acetate
  5. washThe combined organic phases are washed with brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated
  8. customPurification by column chromatography on silica gel (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-75f1eea9453248d1a790e15de0fcd9c2
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163739B2

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