N-bromobutanimide → (+/-)-6-Bromo-2a-methyl-1,2,2a,5-tetrahydropyrrolo[4,3,2-de]quinolin-4(3H)-one

HRID 2426247Notes

Reaction equation

HRID 2426247 reaction equation
[CH3:1][C:2]12[CH2:13][NH:12][C:10]3[C:11]1=[C:6]([CH:7]=[CH:8][CH:9]=3)[NH:5][C:4](=[O:14])[CH2:3]2.[Br:15]N1C(=O)CCC1=O>C(Cl)Cl>[Br:15][C:7]1[C:6]2[NH:5][C:4](=[O:14])[CH2:3][C:2]3([CH3:1])[CH2:13][NH:12][C:10]([C:11]=23)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 576637472a-Methyl-1,2,2a,5-tetrahydropyrrolo[4,3,2-de]quinolin-4(3H)-one

Product 1

HCID 57955363(+/-)-6-Bromo-2a-methyl-1,2,2a,5-tetrahydropyrrolo[4,3,2-de]quinolin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (±)-2a-methyl-1,2,2a,5-tetrahydropyrrolo[4,3,2-de]quinolin-4(3H)-one from Step A (525 mg, 2.79 mmol) in CH2Cl2 (15 mL) at 0° C. was added N-bromosuccinimide (496 mg, 2.79 mmol) and the mixture was allowed to warm slowly to ambient temperature. After 5 h, the reaction mixture was quenched with saturated aqueous NaHCO3 (10 mL) and extracted with EtOAc (150 mL). The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:CH3CN—100:0 to 75:25, to give the title compound. MS: m/z=267 (M+1).

Workup

  1. customthe reaction mixture was quenched with saturated aqueous NaHCO3 (10 mL)
  2. extractionextracted with EtOAc (150 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by silica gel chromatography
  8. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-eef01fabf63a49d18df2954362447f20
Source dataset
uspto-grants-2011_06
Patent number
US07968540B2

Reaction notes

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