Hydrogen Bromide → HCID 19431936, compound

HRID 1077560Notes

Reaction equation

HRID 1077560 reaction equation
N[C:2]1[N:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[C:14]=1[CH2:15][O:16][CH3:17])=[CH:11][C:10]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:9][CH:8]=3.[BrH:26].C(ON=O)CC(C)C>C(Br)(Br)Br.C(Cl)Cl.[Cu]Br>[Br:26][C:2]1[N:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[C:14]=1[CH2:15][O:16][CH3:17])=[CH:11][C:10]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:9][CH:8]=3

Participants

7

Reactant 3

HCID 260Hydrogen BromideHCID 8053Isoamyl NitriteHCID 10837375HCID 10837375, compound

Product 1

HCID 19431936HCID 19431936, compound

Reagents, catalysts & solvents 3

HCID 24593copper(I) bromideCatalystHCID 5558BromoformSolventHCID 6344DichloromethaneSolvent

Procedure

1 g of 3-amino-6-benzyloxy-4-methoxymethyl-β-carboline in 32 ml of bromoform is mixed with 0.6 ml of HBr/glacial acetic acid (33%) and 5 g of PGE200. 0.46 ml of isoamylnitrite is added at 9° C. and it is maintained for 30 minutes at this temperature. Then 0.56 g of copper(I) bromide is added to this batch. After heating of the batch to room temperature it is diluted with methylene chloride within one hour and extracted once each with dilute ammonia solution and with water. The organic phase is dried, filtered and concentrated by evaporation. The residue is chromatographed on silica gel with methylene chloride: ethanol=15:1. The corresponding combined fractions are concentrated by evaporation and absorptively precipitated with ethyl acetate/hexane. 0.54 g of 3-bromo-6-benzyloxy-4-methoxymethyl-β-carboline is obtained.

Workup

  1. temperatureit is maintained for 30 minutes at this temperature
  2. extractionextracted once each with dilute ammonia solution
  3. customThe organic phase is dried
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation
  6. customThe residue is chromatographed on silica gel with methylene chloride
  7. concentrationThe corresponding combined fractions are concentrated by evaporation
  8. customabsorptively precipitated with ethyl acetate/hexane

Sources & evidence

ORD record
ord-600592837c93491bb682924f1b5726ab
Source dataset
uspto-grants-1996_08
Patent number
US05543519

Reaction notes

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