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

HRID 1159824노트

반응식

HRID 1159824 반응식
[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

참가 물질

4

반응물 1

HCID 866182601-[-2-(3-Benzyloxy-6-bromo-2-nitro-phenyl)-vinyl]-pyrrolidine2회

생성물 1

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

시약·촉매·용매 2

HCID 23925Iron촉매HCID 176Acetic Acid용매2회

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-d4dccfae83cf45858a017fcacec8131b
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812017B2

반응 노트

불러오는 중…