Dimethylformamide → 3-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indole-2-carbaldehyde

HRID 352090

反応式

HRID 352090 の反応式
P(Cl)(Cl)(Cl)=O.[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([CH:22]([CH3:24])[CH3:23])[CH:14]=2)=[CH:9][CH:8]=1.[OH-].[Na+].CN([CH:30]=[O:31])C>O>[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([CH:22]([CH3:24])[CH3:23])[C:14]=2[CH:30]=[O:31])=[CH:9][CH:8]=1

参加物

6

反応物 4

HCID 6228Dimethylformamide3 回HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 7362293-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indole

生成物 1

HCID 113120613-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indole-2-carbaldehyde

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
3 °C

実験手順

5.77 g (78.96 mmol) of DMF are weighed into a 100 ml three-necked round-bottomed flask, equipped with a magnetic stirrer, thermometer, dropping funnel, reflux condenser and nitrogen delivery line, and cooled, with stirring, to 3° C. 12.11 g (78.96 mmol) of phosphorus oxychloride are then slowly added dropwise so that the internal temperature does not exceed 10° C. The reaction mixture is then heated to 80° C. and 10 g (39.48 mmol) of 3-(4-fluorophenyl)-1-isopropyl-1H-indole, dissolved in 10 ml of DMF, are added dropwise in the course of 30 min. Stirring is subsequently carried out for 1.5 hours at that temperature. Cooling and dilution with 10 ml of DMF are then carried out. The reaction mixture is transferred into a dropping funnel and, with stirring, slowly added dropwise at 40° C. to 10 g (0.25 mol) of sodium hydroxide in 200 ml of water. The aqueous phase is extracted four times with 50 ml of toluene and the combined organic phases are washed six times with 100 ml of water. Subsequently, 10 g of silica gel are added, the mixture is stirred for 1 hour and filtration is carried out, followed by washing three times with 50 ml of toluene and concentration by evaporation. 10.17 g of a brown oil are obtained, which is dissolved in 100 ml of hexane under reflux. 10 g of silica gel are added, and filtration is carried out while hot, followed by washing three times with 50 ml of hot hexane. The filtrate is concentrated by evaporation and the residue is recrystallised from 94% ethanol. Slightly beige crystals having a melting point of from 89.5 to 91° C. are obtained.

後処理

  1. customequipped with a magnetic stirrer
  2. temperaturereflux condenser
  3. temperaturenitrogen delivery line, and cooled
  4. customdoes not exceed 10° C
  5. temperatureThe reaction mixture is then heated to 80° C.
  6. additionare added dropwise in the course of 30 min
  7. stirringStirring
  8. temperatureCooling
  9. customThe reaction mixture is transferred into a dropping funnel
  10. stirringwith stirring
  11. extractionThe aqueous phase is extracted four times with 50 ml of toluene
  12. washthe combined organic phases are washed six times with 100 ml of water
  13. additionSubsequently, 10 g of silica gel are added
  14. stirringthe mixture is stirred for 1 hour
  15. filtrationfiltration
  16. washby washing three times
  17. concentrationwith 50 ml of toluene and concentration
  18. customby evaporation

出典と根拠

ORDレコード
ord-6bd3a8920a744189bd3e256dea8ef4eb
出典データセット
uspto-grants-2004_06
特許番号
US06743926B2

関連ノート

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