N-bromobutanimide → HCID 90409014, compound

HRID 589020Notes

Reaction equation

HRID 589020 reaction equation
[C:1]1([CH:7]2[N:12]3[C:13](=[O:19])[NH:14][C:15]4=[CH:16][CH:17]=[CH:18][C:10](=[C:11]34)[O:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20]N1C(=O)CCC1=O>CC(O)=O>[Br:20][C:18]1[C:10]2[O:9][CH2:8][CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:12]3[C:13](=[O:19])[NH:14][C:15]([C:11]=23)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 90409251HCID 90409251, compound

Product 1

HCID 90409014HCID 90409014, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4-phenyl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazin-2(1H)-one (400 mg, 2 mmol) and N-bromosuccinimide (310 mg, 1.7 mmol) in AcOH (10 mL) was stirred at room temperature for 2 h. The reaction mixture was allowed to cool and was concentrated to remove AcOH. The residue was taken up in EtOAc and was washed with water saturated NaHCO3, brine, dried over magnesium sulfate, filtered and concentrated to give crude product. The product was purified by flash column chromatography on a Biotage system eluting with a hexane: EtOAc gradient (0-40%) to give 7-bromo-4-phenyl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazin-2(1H)-one as an amber oil (0.30 g, 60%). LCMS calc. for C15H12BrN2O2 (M+H)+: m/z=331.1, 333.1. found: 331.0, 333.0. 1H NMR (300 MHz, CD3OD) δ 7.42-7.23 (m, 3H), 7.23-7.09 (m, 3H), 6.70 (d, J=8.4 Hz, 1H), 5.46 (dd, J=2.6 Hz, 1H), 4.66 (dd, J=11.6, 2.4 Hz, 1H), 4.47 (dd, J=11.6, 3.1 Hz, 1H).

Workup

  1. temperatureto cool
  2. concentrationwas concentrated
  3. customto remove AcOH
  4. washwas washed with water saturated NaHCO3, brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give crude product
  9. customThe product was purified by flash column chromatography on a Biotage system
  10. washeluting with a hexane

Sources & evidence

ORD record
ord-b89eafa6c4d94639a129e7f97f8bbb92
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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