Bromine → Eudistomin O

HRID 1168715Notes

Reaction equation

HRID 1168715 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[NH:13][C:12]3[CH:11]=[N:10][CH:9]=[CH:8][C:7]=3[C:5]=2[CH:6]=1.[Br:14]Br>O1CCCC1>[Br:14][C:2]1[CH:3]=[C:4]2[C:5]([C:7]3[CH:8]=[CH:9][N:10]=[CH:11][C:12]=3[NH:13]2)=[CH:6][CH:1]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 64961Beta-Carboline

Product 1

HCID 145928Eudistomin OYield 65.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of norharmane (600 mg, 3.57 mmol) in tetrahydrofuran (THF; 50 ml) was treated with bromine (0.40 ml, 7.80 mmol) at RT while stirring. After stirring for 18 h at RT, the reaction was concentrated under reduced pressure and the resulting residue was sonicated in 10% aqueous Na2CO3 (100 ml). The product was filtered and washed with water to give 905 mg of crude product. The crude product was crystallized from xylenes to provide in two crops 580 mg of 7-bromo-β-carboline.

Workup

  1. stirringAfter stirring for 18 h at RT
  2. concentrationthe reaction was concentrated under reduced pressure
  3. customthe resulting residue was sonicated in 10% aqueous Na2CO3 (100 ml)
  4. filtrationThe product was filtered
  5. washwashed with water
  6. customto give 905 mg of crude product
  7. customThe crude product was crystallized from xylenes

Sources & evidence

ORD record
ord-4d0ad88717a943eeb5254d57152975b3
Source dataset
uspto-grants-2003_09
Patent number
US06627637B2

Reaction notes

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