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

HRID 269956

反応式

HRID 269956 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-0b0ef256a0644ea5beb904af44b7387e
出典データセット
uspto-grants-2008_11
特許番号
US07449478B2

関連ノート

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