Chloroform → 7,9-Dibromo-beta-carboline hydrochloride

HRID 1168719Notes

Reaction equation

HRID 1168719 reaction equation
[Br:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][N:9]=[CH:10][C:11]=3[NH:12]2)=[CH:4][CH:3]=1.[Br:15]Br.C(Cl)(Cl)[Cl:18]>C1COCC1>[ClH:18].[Br:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][N:9]=[CH:10][C:11]=3[N:12]2[Br:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 24408BromineHCID 145928Eudistomin O

Product 1

HCID 221852417,9-Dibromo-beta-carboline hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product from example 1 (140 mg, 0.58 mmol) in THF (2 ml) was treated with bromine (0.50 ml). After 10 min at RT, the reaction was diluted with chloroform and the product was filtered. The filtered product was taken up in methanol and treated with 1M HCl in ether and concentrated. The residue was triturated with ether to provide 160 mg of 7,9-dibromo-β-carboline hydrochloride.

Workup

  1. filtrationthe product was filtered
  2. additiontreated with 1M HCl in ether
  3. concentrationconcentrated
  4. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-52b42d2aed7643979ed7dd67d71e2d1c
Source dataset
uspto-grants-2003_09
Patent number
US06627637B2

Reaction notes

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