Triethylamine → 7-Bromo-9-fluoro-4-pyridin-3-yl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazin-2(1H)-one

HRID 589135Notes

Reaction equation

HRID 589135 reaction equation
C(N(CC)CC)C.[Br:8][C:9]1[CH:10]=[C:11]([F:26])[C:12]([NH2:25])=[C:13]2[C:18]=1[O:17][CH2:16][CH:15]([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)[NH:14]2.Cl[C:28](Cl)([O:30]C(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1.O>[Br:8][C:9]1[C:18]2[O:17][CH2:16][CH:15]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[N:14]3[C:28](=[O:30])[NH:25][C:12]([C:13]=23)=[C:11]([F:26])[CH:10]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 904097398-Bromo-6-fluoro-3-pyridin-3-yl-3,4-dihydro-2H-1,4-benzoxazin-5-amine

Product 1

HCID 904103367-Bromo-9-fluoro-4-pyridin-3-yl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (140 μL, 1.0 mmol) was added to a solution of 8-bromo-6-fluoro-3-pyridin-3-yl-3,4-dihydro-2H-1,4-benzoxazin-5-amine (160 mg, 0.50 mmol)) in THF (6.0 mL), followed by addition of triphosgene (60 mg, 0.2 mmol), and the mixture was subsequently stirred at room temperature for 10 min. The mixture was diluted with water and extracted with ethyl acetate. The organic extracts were washed with brine and concentrated. Purification on silica gel eluting ethyl acetate in hexanes afforded the title compound. LCMS calc. for C14H10BrFN3O2 (M+H)+: m/z=350.0. found: 350.0.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic extracts were washed with brine
  3. concentrationconcentrated
  4. customPurification on silica gel
  5. washeluting ethyl acetate in hexanes

Sources & evidence

ORD record
ord-8782d4cde2ce498ab54724fb7674bc83
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

Loading…