Water → Ethyl 2-(4-nitrophenyl)-1,3-thiazole-5-carboxylate

HRID 1425032노트

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HRID 1425032 반응식
O.[N+:2]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)([O-:4])=[O:3].Br[C:15]1[S:16][C:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][N:19]=1.C(=O)(O)[O-].[Na+]>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.C(OCC)(=O)C.O1CCOCC1>[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([C:15]2[S:16][C:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][N:19]=2)=[CH:7][CH:6]=1)([O-:4])=[O:3]

참가 물질

8

반응물 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 27735524-Nitrophenylboronic acidHCID 3614103Ethyl 2-bromothiazole-5-carboxylate

생성물 1

HCID 53403660Ethyl 2-(4-nitrophenyl)-1,3-thiazole-5-carboxylate수율 54%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

Water (5 mL) and 1,4-dioxane (5 mL) were added to 4-nitrophenylboronic acid (667 mg, 4 mmol), ethyl 2-bromo-1,3-thiazole-5-carboxylate (448 μL, 4 mmol), sodium bicarbonate (1.01 g, 12 mmol) and tetrakis(triphenylphosphine)palladium (462 mg, 0.4 mmol), and the mixture was stirred in a nitrogen atmosphere at 100° C. for 1.5 hours. Ethyl acetate was added to the reaction solution, and the organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. Following concentration under reduced pressure, the residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=10/1, 4/1, 2/1) to obtain 0.6 g of the title compound as a colorless solid (54%).

후처리

  1. washthe organic layer was washed with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentration under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=10/1, 4/1, 2/1)

출처 및 근거

ORD 기록
ord-7c3f11bf0f204cd684a4e093e10407b7
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927588B2

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