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

HRID 551094Notes

Reaction equation

HRID 551094 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:CH3CN —100:0 to 75:25

Sources & evidence

ORD record
ord-f30f865b87304f0cae03f9503ec43730
Source dataset
uspto-grants-2011_05
Patent number
US07947677B2

Reaction notes

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