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

HRID 656067ノート

反応式

HRID 656067 の反応式
[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

参加物

5

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 14801Manganese dioxide触媒HCID 313Hydrochloric Acid溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5925b50d9a064015900ea213439de480
出典データセット
uspto-grants-2011_12
特許番号
US08071584B2

反応ノート

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