Water → ethyl 1-{[4-(3-acetylphenyl)-1,3-thiazol-2-yl]methyl}-1H-pyrazole-4-carboxylate

HRID 1257342노트

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HRID 1257342 반응식
Br[C:2]1[N:3]=[C:4]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:10]=[N:9]2)[S:5][CH:6]=1.[C:18]([C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1)(=[O:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+].O>COCCOC.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:18]([C:21]1[CH:26]=[C:25]([C:2]2[N:3]=[C:4]([CH2:7][N:8]3[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:10]=[N:9]3)[S:5][CH:6]=2)[CH:24]=[CH:23][CH:22]=1)(=[O:20])[CH3:19]

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27343103-Acetylphenylboronic acidHCID 58127892ethyl 1-[(4-bromo-1,3-thiazol-2-yl)methyl]-1H-pyrazole-4-carboxylate

생성물 1

HCID 58127487ethyl 1-{[4-(3-acetylphenyl)-1,3-thiazol-2-yl]methyl}-1H-pyrazole-4-carboxylate수율 67%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

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온도
120 °C

실험 절차

Under an argon atmosphere, to a solution (4 mL) of the compound (250 mg, 0.79 mmol) obtained in Example 30c in 1,2-dimethoxyethane were added (3-acetylphenyl)boronic acid (156 mg, 0.95 mmol), potassium carbonate (218 mg, 1.58 mmol) and tetrakistriphenylphosphinepalladium (91 mg, 0.079 mmol), and the mixture was stirred at 120° C. for 15 min under microwave conditions. The mixture was allowed to cool to room temperature, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The obtained crude product was purified by column chromatography (hexane-hexane/ethyl acetate=1/1) to give the title compound (188 mg, 67%) as a pale-brown oil.

후처리

  1. temperatureto cool to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe obtained organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe obtained crude product
  7. customwas purified by column chromatography (hexane-hexane/ethyl acetate=1/1)

출처 및 근거

ORD 기록
ord-06dc9de19fe84b49830064949771c52e
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461348B2

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