Potassium Iodide → 6-[3-(1H-indol-4-yloxy)-propoxy]-7-propyl-3-trifluoromethyl-benzo[d]isoxazole

HRID 269956

반응식

HRID 269956 반응식
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2.[CH2:15]([C:18]1[C:26]2[O:25][N:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[C:22]=2[CH:21]=[CH:20][C:19]=1[OH:31])[CH2:16][CH3:17].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(OCC)(=O)C.O.CN(C=O)C>[NH:10]1[C:11]2[C:7](=[C:6]([O:5][CH2:4][CH2:3][CH2:2][O:31][C:19]3[CH:20]=[CH:21][C:22]4[C:23]([C:27]([F:30])([F:29])[F:28])=[N:24][O:25][C:26]=4[C:18]=3[CH2:15][CH2:16][CH3:17])[CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:9]1

참가 물질

8

반응물 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 116941694-(3-chloropropoxy)-1H-indoleHCID 1358008127-Propyl-3-(trifluoromethyl)benzo[d]isoxazol-6-ol

생성물 1

HCID 115245536-[3-(1H-indol-4-yloxy)-propoxy]-7-propyl-3-trifluoromethyl-benzo[d]isoxazole수율 78%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
110 °C

실험 절차

4-(3-Chloropropoxy)-1H-indole (0.100 g, 0.48 mmol), 7-propyl-3-trifluoromethyl-benzo[d]isoxazol-6-ol (0.117 g, 0.48 mmol), potassium carbonate (0.099 g, 0.72 mmol), potassium iodide (0.016 g, 0.10 mmol), and DMF (5 mL) were mixed and heated at 110° C. for 1.5 hours. The mixture was cooled to room temperature. Water (10 mL) and ethyl acetate (10 mL) were added and the resultant mixture was stirred for five minutes. The organic layer was separated and aqueous layer was extracted again with ethyl acetate (10 mL). The organic layer was combined, washed with water (6×20 mL) and brine (2×20 mL), and dried over anhydrous Na2SO4. The solvent was removed in vacuo to give an oily residue, which was purified by filtering through a short silica column using hexane/dichloromethane (50/50) as an eluant to afford 6-[3-(1H-indol-4-yloxy)-propoxy]-7-propyl-3-trifluoromethyl-benzo[d]isoxazole (0.156 g, yield: 78%).

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. extractionaqueous layer was extracted again with ethyl acetate (10 mL)
  4. washwashed with water (6×20 mL) and brine (2×20 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. customThe solvent was removed in vacuo
  7. customto give an oily residue, which
  8. customwas purified
  9. filtrationby filtering through a short silica column

출처 및 근거

ORD 기록
ord-0b0ef256a0644ea5beb904af44b7387e
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449478B2

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