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

HRID 928553노트

반응식

HRID 928553 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a8789a267a304d48a93e98e22c07c4f6
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290514B2

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