Carbon Dioxide → 5-chloro-1H-indole-7-carboxylic acid

HRID 855236

반응식

HRID 855236 반응식
Br[C:2]1[CH:3]=[C:4]([Cl:11])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.C([Li])CCC.[C:17](=[O:19])=[O:18].O>C1COCC1.CCCCCC>[Cl:11][C:4]1[CH:5]=[C:6]2[C:10](=[C:2]([C:17]([OH:19])=[O:18])[CH:3]=1)[NH:9][CH:8]=[CH:7]2

참가 물질

7

반응물 4

HCID 280Carbon DioxideHCID 962WaterHCID 247295047-bromo-5-chloro-1H-indoleHCID 178418339Butyllithium

생성물 1

HCID 668685635-chloro-1H-indole-7-carboxylic acid수율 72%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

반응 조건

온도
5 °C

실험 절차

1.15 g (5 mmol) of 7-bromo-5-chloro-1H-indole were dissolved in 30 ml THF. At a temperature of −75° C. under argon 9.4 ml (15 mmol) of a 1.6 M n-butyl lithium solution in hexane were added dropwise. After complete addition the reaction mixture was stirred at 5° C. for 30 min, cooled to −75° C. and 10 g dry ice was added. The reaction mixture was warmed to rt and stirred for 15 min. It was poured onto 100 ml of water and extracted twice with EtOAc. The aqueous layer was acidified with 1N aqueous HCl solution and extracted twice with DCM. The combined organic layers were dried over sodium sulfate, filtered and the solvent was evaporated. The residue was treated with hexane and stirred for 10 min. The precipitate was filtered, washed with hexane and dried to yield 700 mg (72%) of 5-chloro-1H-indole-7-carboxylic acid as a white solid. MS (ISP) 194.0 (M−H)−.

후처리

  1. additionAfter complete addition the reaction mixture
  2. temperaturecooled to −75° C.
  3. temperatureThe reaction mixture was warmed to rt
  4. stirringstirred for 15 min
  5. extractionextracted twice with EtOAc
  6. extractionextracted twice with DCM
  7. dry with materialThe combined organic layers were dried over sodium sulfate
  8. filtrationfiltered
  9. customthe solvent was evaporated
  10. additionThe residue was treated with hexane
  11. stirringstirred for 10 min
  12. filtrationThe precipitate was filtered
  13. washwashed with hexane
  14. customdried

출처 및 근거

ORD 기록
ord-97b659aed26e4d91af804825204b3d7b
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259183B2

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