5-bromo-6-fluoro-2,3-dihydro-1H-indole-7-carboxylic acid → 5-bromo-6-fluoro-1H-indole-7-carboxylic acid

HRID 387306노트

반응식

HRID 387306 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:12]([OH:14])=[O:13])[C:10]=1[F:11])[NH:7][CH2:6][CH2:5]2>C1COCC1.Cl.O=[Mn]=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:12]([OH:14])=[O:13])[C:10]=1[F:11])[NH:7][CH:6]=[CH:5]2

참가 물질

5

반응물 1

HCID 593326645-bromo-6-fluoro-2,3-dihydro-1H-indole-7-carboxylic acid

생성물 1

HCID 593327305-bromo-6-fluoro-1H-indole-7-carboxylic acid수율 61.7%

시약·촉매·용매 3

HCID 14801Manganese dioxide촉매HCID 313Hydrochloric Acid용매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 5-bromo-6-fluoro-2,3-dihydro-1H-indole-7-carboxylic acid (5.8 g, 0.022 mol) in THF (120 mL) was added MnO2 (11.6 g, 0.134 mol). The reaction mixture was stirred at reflux overnight and then filtered (hot) through celite, washing with hot THF (2×75 mL). The filtrate was concentrated, giving a brown solid, which was suspended in 1M HCl (150 mL). The mixture stirred at reflux overnight to remove traces of Mn and then cooled to room temperature. The solid was filtered off, dried, and recrystallised from IPA, giving 3.5 g (61%) of the title compound.

후처리

  1. temperatureat reflux overnight
  2. filtrationfiltered (hot) through celite
  3. washwashing with hot THF (2×75 mL)
  4. concentrationThe filtrate was concentrated
  5. customgiving a brown solid, which
  6. stirringThe mixture stirred
  7. temperatureat reflux overnight
  8. customto remove traces of Mn
  9. filtrationThe solid was filtered off
  10. customdried
  11. customrecrystallised from IPA

출처 및 근거

ORD 기록
ord-e454036211f046d8979dc2edad596eef
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372875B2

반응 노트

불러오는 중…