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

HRID 1159824Notes

Reaction equation

HRID 1159824 reaction equation
[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

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-d4dccfae83cf45858a017fcacec8131b
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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