Sodium Carbonate → 4-(Benzo[b]thiophen-5-yl)-3,5-dimethylisoxazole

HRID 1009003노트

반응식

HRID 1009003 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.[CH3:11][C:12]1[C:16](C(B(O)O)=O)=[C:15]([CH3:22])[O:14][N:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C(O)C>[S:9]1[CH:8]=[CH:7][C:6]2[CH:10]=[C:2]([C:16]3[C:12]([CH3:11])=[N:13][O:14][C:15]=3[CH3:22])[CH:3]=[CH:4][C:5]1=2

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 27765785-Bromo-1-benzothiopheneHCID 673054143,5-Dimethyl-4-isoxazoylboronic acid

생성물 1

HCID 534868054-(Benzo[b]thiophen-5-yl)-3,5-dimethylisoxazole수율 60.2%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
80 °C

실험 절차

To a solution of 5-bromo-1-benzothiophene (ABCR, CAS: 133150-64-8, 1.0 6 g, 5.0 mmol) in dimethoxyethane (60 mL) and ethanol (6.0 mL) was added 3,5-dimethyl-4-isoxazoylboronic acid (1.0 g, 7.5 mmol), and 2 m sodium carbonate (2.0 mL). The reaction mixture was degassed 2-3 times, tetrakis-(triphenylphosphine)palladium (0.813 g, 0.7 mmol) was added, and the mixture was stirred for 6 h at 80° C. and concentrated. The residue was taken up in water and extracted with ethyl acetate. The organics were washed, dried and concentrated. The crude product was chromatographed on silica gel using heptane/ethyl acetate as eluent to obtain 4-benzo[b]thiophen-5-yl-3,5-dimethyl-isoxazole (0.69 g) as a light yellow solid. MS (ISP): m/e 230.1 (M+H)+

후처리

  1. additionwas added
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate
  4. washThe organics were washed
  5. customdried
  6. concentrationconcentrated
  7. customThe crude product was chromatographed on silica gel

출처 및 근거

ORD 기록
ord-38a7e0a2adcd4b80ab7c45ce2197dfc2
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973051B2

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