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

HRID 1795082Notes

Reaction equation

HRID 1795082 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-6eb329c436024a6182d9a087d081bb92
Source dataset
uspto-grants-2006_04
Patent number
US07026331B2

Reaction notes

Loading…