Dimethylformamide → HCID 22490569、化合物

HRID 2180870ノート

反応式

HRID 2180870 の反応式
C(O[C:4]([NH:6][C:7]1[CH:8]=[C:9]([C:14]([F:17])([F:16])[F:15])[CH:10]=[CH:11][C:12]=1I)=O)C.C[O:19][CH:20]1[CH:24]=[CH:23]C(OC)[O:21]1.C(N(C(C)C)CC)(C)C.CN(C=O)C>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.O>[F:17][C:14]([F:15])([F:16])[C:9]1[CH:8]=[C:7]2[C:12]([C:23]([CH2:24][C:20]([OH:21])=[O:19])=[CH:4][NH:6]2)=[CH:11][CH:10]=1

参加物

9

反応物 4

HCID 6228DimethylformamideHCID 789742,5-Dihydro-2,5-dimethoxyfuranHCID 81531DiisopropylethylamineHCID 22490680HCID 22490680、化合物

生成物 1

HCID 22490569HCID 22490569、化合物収率 6.3%

試薬・触媒・溶媒 4

HCID 66133Benzyl triethylammonium chloride触媒HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

A mixture of 3-ethoxycarbonylamino-4-iodobenzotrifluoride (1.8 g), 2,5-dihydro-2,5-dimethoxyfuran (1.3 g), palladium acetate (60 mg), diisopropylethylamine (2.0 g), benzyltriethylammonium chloride (1.2 g) and DMF (15 ml) was stirred for 20 hours under a nitrogen atmosphere at 80° C. Water and ethyl acetate were added to the reaction mixture, the insoluble portion was filtered out with celite, and extraction was performed with ethyl acetate. The organic layer was collected and dried over sodium sulfate and then concentrated under reduced pressure. Dichloromethane (25 ml) and trifluoroacetic acid (1.5 ml) were added to the obtained residue, and the mixture was stirred at room temperature for 2 hours. Saturated sodium bicarbonate water was added to the reaction mixture and vigorously stirred therewith. The organic layer was collected and dried over sodium sulfate and then concentrated under reduced pressure. A (1-ethoxycarbonyl-6-trifluoromethyl-1H-indol-3-yl)acetic acid methyl ester component was purified from the obtained residue by silica gel column chromatography using a mixed solvent of hexane and ethyl acetate. A 2 N sodium hydroxide aqueous solution (1 ml) and methanol (1 ml) were added to the obtained (1-ethoxycarbonyl-6-trifluoromethyl-1H-indol-3-yl)acetic acid methyl ester, and the mixture was heated to reflux for one hour. Water was added to the reaction mixture, which was then rendered acidic with concentrated aqueous hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure, to obtain 77 mg of the title compound as a colorless powder (5% yield).

後処理

  1. filtrationthe insoluble portion was filtered out with celite, and extraction
  2. customThe organic layer was collected
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionDichloromethane (25 ml) and trifluoroacetic acid (1.5 ml) were added to the obtained residue
  6. stirringthe mixture was stirred at room temperature for 2 hours
  7. additionSaturated sodium bicarbonate water was added to the reaction mixture
  8. stirringvigorously stirred
  9. customThe organic layer was collected
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customA (1-ethoxycarbonyl-6-trifluoromethyl-1H-indol-3-yl)acetic acid methyl ester component was purified from the obtained residue by silica gel column chromatography
  13. additionA 2 N sodium hydroxide aqueous solution (1 ml) and methanol (1 ml) were added to the obtained (1-ethoxycarbonyl-6-trifluoromethyl-1H-indol-3-yl)acetic acid methyl ester
  14. temperaturethe mixture was heated
  15. temperatureto reflux for one hour
  16. additionWater was added to the reaction mixture, which
  17. extractionrendered acidic with concentrated aqueous hydrochloric acid and extracted with ethyl acetate
  18. dry with materialThe organic layer was dried over sodium sulfate
  19. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-f41ddd91282a47c896cba5ec3733147b
出典データセット
uspto-grants-2005_05
特許番号
US06887890B2

反応ノート

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