Dimethylformamide → 1-Acetyl-7-bromo-beta-carboline

HRID 1393978Notes

Reaction equation

HRID 1393978 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:16]=[C:15]2[C:7]([C:8]3[CH:9]=[CH:10][N:11]=[CH:12][C:13]=3[NH:14]2)=[CH:6][CH:5]=1.[CH3:17]S(Cl)(=O)=O.CN([CH:25]=[O:26])C>>[C:25]([C:12]1[C:13]2[NH:14][C:15]3[C:7](=[CH:6][CH:5]=[C:4]([Br:3])[CH:16]=3)[C:8]=2[CH:9]=[CH:10][N:11]=1)(=[O:26])[CH3:17]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 145928Eudistomin O

Product 1

HCID 221852771-Acetyl-7-bromo-beta-carboline

Procedure

To a suspension of NaH (95%, 14 mg, 0.60 mmol) in DMF (1.0 ml) at 5° C. to 10° C. was added the product from example 1 (74 mg, 0.30 mmol). The resulting mixture was stirred for 15 min at 5° C. to 10° C. before adding methanesulfonylchloride (0.030 ml, 0.38 mmol). The reaction was allowed to warm to RT and stirred for 2 h before partitioning into saturated aqueous NaHCO3 and EtOAc. After stirring the mixture overnight, the organic layer was washed with water, dried (brine; MgSO4), and concentrated. The residue was purified by chromatography (1:1 hexane-ethyl acetate) on silica gel to give 23 mg of 1-acetyl-7-bromo-β-carboline.

Workup

  1. stirringstirred for 2 h
  2. custombefore partitioning into saturated aqueous NaHCO3 and EtOAc
  3. stirringAfter stirring the mixture overnight
  4. washthe organic layer was washed with water
  5. dry with materialdried (brine; MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (1:1 hexane-ethyl acetate) on silica gel

Sources & evidence

ORD record
ord-92d5ea1af9074618ac412cf4169730b1
Source dataset
uspto-grants-2008_03
Patent number
US07348336B2

Reaction notes

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