1-[-2-(3-Benzyloxy-6-bromo-2-nitro-phenyl)-vinyl]-pyrrolidine → 7-(Benzyloxy)-4-bromo-1H-indole

HRID 1159824ノート

反応式

HRID 1159824 の反応式
[CH2:1]([O:8][C:9]1[C:10]([N+:23]([O-])=O)=[C:11]([CH:16]=[CH:17]N2CCCC2)[C:12]([Br:15])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CC(O)=O.[Fe]>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[C:11]2[C:10]=1[NH:23][CH:17]=[CH:16]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 1

HCID 866182601-[-2-(3-Benzyloxy-6-bromo-2-nitro-phenyl)-vinyl]-pyrrolidine2 回

生成物 1

HCID 114608287-(Benzyloxy)-4-bromo-1H-indole

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 176Acetic Acid溶媒2 回

実験手順

1-[-2-(3-Benzyloxy-6-bromo-2-nitro-phenyl)-vinyl]-pyrrolidine (10 g, 24.8 mmol; Intermediate 82) suspended in HOAc (25 mL) was added to a boiling mixture of iron (4.15 g, 74.4 mmol) in HOAc. After 2 h boiling TLC indicated that no starting material is left. The reaction mixture was filtered while still warm. The residue was evaporated and dissolved in toluene. The toluene slurry was applied to a silica column and eluted with toluene/hexane 1/1. Obtained 3.1 g. MS (ESI+) for C15H12BrNO m/z 302, 304 (M+H)+.

後処理

  1. waitis left
  2. filtrationThe reaction mixture was filtered
  3. temperaturewhile still warm
  4. customThe residue was evaporated
  5. dissolutiondissolved in toluene
  6. washeluted with toluene/hexane 1/1
  7. customObtained 3.1 g

出典と根拠

ORDレコード
ord-d4dccfae83cf45858a017fcacec8131b
出典データセット
uspto-grants-2010_10
特許番号
US07812017B2

反応ノート

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