Water → 8-bromo-6-fluoro-5-nitro-3-pyridin-3-yl-3,4-dihydro-2H-1,4-benzoxazin-3-ol

HRID 928553Notes

Reaction equation

HRID 928553 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([F:11])[CH:5]=[C:4]([Br:12])[C:3]=1[OH:13].C(=O)([O-])[O-].[K+].[K+].Br.Br[CH2:22][C:23]([C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1)=[O:24].O>CC(C)=O>[Br:12][C:4]1[C:3]2[O:13][CH2:22][C:23]([C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)([OH:24])[NH:1][C:2]=2[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([F:11])[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27762343-(2-Bromoacetyl)pyridine hydrobromideHCID 904098182-Amino-6-bromo-4-fluoro-3-nitrophenol

Product 1

HCID 904096628-bromo-6-fluoro-5-nitro-3-pyridin-3-yl-3,4-dihydro-2H-1,4-benzoxazin-3-ol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Amino-6-bromo-4-fluoro-3-nitrophenol (500 mg, 1.9 mmol) and potassium carbonate (780 mg, 5.7 mmol) were stirred in acetone (8 mL) for 5 minutes and 2-bromo-1-pyridin-3-ylethanone hydrobromide (530 mg, 1.9 mmol) was added as a solid over 5 minutes. The mixture was stirred at rt for 5 minutes and poured into water. The mixture was extracted with ethyl acetate. The extracts were washed with brine, dried over sodium sulfate, filtered and evaporated. Purification on silica gel using ethyl acetate in hexanes gave the desired compound, 0.69 g, 99%. LCMS calculated for C13H10BrFN3O4 (M+H)+: m/z=370.1, 372.1. found: 370.0, 372.0.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customPurification on silica gel

Sources & evidence

ORD record
ord-a8789a267a304d48a93e98e22c07c4f6
Source dataset
uspto-grants-2016_03
Patent number
US09290514B2

Reaction notes

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