Acetic Anhydride → 1-Acetyl-7-bromo-beta-carboline

HRID 1393973Notes

Reaction equation

HRID 1393973 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.[OH-].[Na+].[C:17](OC(=O)C)(=[O:19])[CH3:18]>CN(C)C=O>[C:17]([C:10]1[C:11]2[NH:12][C:13]3[C:5](=[CH:4][CH:3]=[C:2]([Br:1])[CH:14]=3)[C:6]=2[CH:7]=[CH:8][N:9]=1)(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 145928Eudistomin O

Product 1

HCID 221852771-Acetyl-7-bromo-beta-carbolineYield 36.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Example 1 (25 mg, 0.1 mmol) in dimetylformamide (DMF; 2 ml) was treated with 0.10 ml of 1M aqueous NaOH (0.10 mmol). After stirring at RT for 30 minutes, acetic anhydride (0.010 ml, 0.095 mmol) was added and reaction stirred 18 h at RT. The reaction was partitioned in EtOAc and 5% citric acid and the organic layer washed with water, dried (brine; MgSO4), and concentrated to give 23 mg of crude product. The crude product was chromatographed (7:3 hexane-acetone) on silica gel to give 10 mg of 1-acetyl-7-bromo-β-carboline.

Workup

  1. customreaction
  2. stirringstirred 18 h at RT
  3. customThe reaction was partitioned in EtOAc
  4. wash5% citric acid and the organic layer washed with water
  5. dry with materialdried (brine; MgSO4)
  6. concentrationconcentrated
  7. customto give 23 mg of crude product
  8. customThe crude product was chromatographed (7:3 hexane-acetone) on silica gel

Sources & evidence

ORD record
ord-131799ddd4424559a30e01c7c6a82d56
Source dataset
uspto-grants-2008_03
Patent number
US07348336B2

Reaction notes

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