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Water → 4-{5-[3-(trifluoromethyl)-4-(2,2,2-trifluoro-1-methylethoxy)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indole-3-carboaldehyde

HRID 552862
ノート
印刷プレビュー

反応式

HRID 552862 の反応式
O=P(Cl)(Cl)Cl.[F:6][C:7]([F:36])([F:35])[C:8]1[CH:9]=[C:10]([C:21]2[O:25][N:24]=[C:23]([C:26]3[CH:34]=[CH:33][CH:32]=[C:31]4[C:27]=3[CH:28]=[CH:29][NH:30]4)[N:22]=2)[CH:11]=[CH:12][C:13]=1[O:14][CH:15]([CH3:20])[C:16]([F:19])([F:18])[F:17].[OH-].[Na+].O.CN([CH:43]=[O:44])C>>[F:36][C:7]([F:6])([F:35])[C:8]1[CH:9]=[C:10]([C:21]2[O:25][N:24]=[C:23]([C:26]3[CH:34]=[CH:33][CH:32]=[C:31]4[C:27]=3[C:28]([CH:43]=[O:44])=[CH:29][NH:30]4)[N:22]=2)[CH:11]=[CH:12][C:13]=1[O:14][CH:15]([CH3:20])[C:16]([F:17])([F:18])[F:19]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 5

HCID 962WaterHCID 6228Dimethylformamide2 回HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 592141764-{5-[3-(trifluoromethyl)-4-(2,2,2-trifluoro-1-methylethoxy)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indole

生成物 1

HCID 59214403
4-{5-[3-(trifluoromethyl)-4-(2,2,2-trifluoro-1-methylethoxy)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indole-3-carboaldehyde

実験手順

POCl3 (158.4 μl) was added dropwise to a DMF solution (4 ml) at 0° C. After warming to room temperature, it was stirred for 0.5 hour. Then, a solution of 4-{5-[3-(trifluoromethyl)-4-(2,2,2-trifluoro-1-methylethoxy)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indole (500.0 mg) in DMF (1 ml) was added thereto at 0° C., followed by stirring at room temperature for 15 hours. After cooling to 0° C., to the reaction solution was added a 1M aqueous NaOH solution for adjustment of its pH to 9 to 10. This solution was stirred at 100° C. for 1 hour. After being left to be cooled, to the reaction solution was added water (30 ml), followed by extraction three times with EtOAc (20 ml). The organic layer was combined, washed with saturated brine, dried over anhydrous MgSO4, and then filtered, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (automatic purifier, n-hexane, EtOAc=90:10 to 70:30) to obtain 4-{5-[3-(trifluoromethyl)-4-(2,2,2-trifluoro-1-methylethoxy)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indole-3-carboaldehyde (456.7 mg) as a white solid.

後処理

  1. customat 0° C.
  2. stirringby stirring at room temperature for 15 hours
  3. temperatureAfter cooling to 0° C., to the reaction solution
  4. stirringThis solution was stirred at 100° C. for 1 hour
  5. waitAfter being left
  6. temperatureto be cooled, to the reaction solution
  7. extractionfollowed by extraction three times with EtOAc (20 ml)
  8. washwashed with saturated brine
  9. dry with materialdried over anhydrous MgSO4
  10. filtrationfiltered
  11. concentrationthe filtrate was concentrated
  12. customThe residue was purified by silica gel column chromatography (automatic purifier, n-hexane, EtOAc=90:10 to 70:30)

出典と根拠

ORDレコード
ord-fbf3a5d5b1624876a07428c7fbd5e0ba
出典データセット
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07951825B2

反応ノート

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