Eudistomin O → 7-Cyano-beta-carboline

HRID 1168718Notes

Reaction equation

HRID 1168718 reaction equation
Br[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.[C:15]([Cu])#[N:16]>CN1CCCC1=O>[C:15]([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)#[N:16]

Participants

4

Reactant 2

HCID 145928Eudistomin OHCID 178418546HCID 178418546, compound

Product 1

HCID 221852237-Cyano-beta-carbolineYield 6.7%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A dark solution of example 1 (190 mg, 0.62 mmol) and CuCN (110 mg, 1.22 mmol) in N-methyl 2-pyrrolidone (1.5 ml) was heated in a sealed reaction tube at 200° C. for 48 h. The mixture was filtered and the filtrate was diluted with water (50 ml). A brown solid that precipitated was filtered, washed with water, saturated aqueous NaHCO3, and then methanol. This material was dissolved in DMSO and diluted with aqueous HCl. This homogeneous dark solution was decolorized with charcoal, filtered and concentrated to give a concentrated solution in DMSO. This DMSO solution was partitioned in (1:1) EtOAc-THF and saturated aqueous NaHCO3. The organic solution was dried (MgSO4) and concentrate to give 8 mg of 7-cyano-β-carboline.

Workup

  1. filtrationThe mixture was filtered
  2. additionthe filtrate was diluted with water (50 ml)
  3. filtrationA brown solid that precipitated was filtered
  4. washwashed with water, saturated aqueous NaHCO3
  5. dissolutionThis material was dissolved in DMSO
  6. additiondiluted with aqueous HCl
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a concentrated solution in DMSO
  10. customThis DMSO solution was partitioned in (1:1) EtOAc-THF
  11. dry with materialThe organic solution was dried (MgSO4)
  12. concentrationconcentrate

Sources & evidence

ORD record
ord-b6aaa8ecf0cc43f7bc9c1aa7d9273098
Source dataset
uspto-grants-2003_09
Patent number
US06627637B2

Reaction notes

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