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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Hydrogen Peroxide → 5-Bromo-3-(trifluoromethyl)pyrazin-2-amine

HRID 244584
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HRID 244584 반응식
[NH2:1][C:2]1[CH:7]=[N:6][C:5]([Br:8])=[CH:4][N:3]=1.[C:9](I)([F:12])([F:11])[F:10].OO>CS(C)=O.[Cl-].[Na+].O.[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2]>[Br:8][C:5]1[N:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[C:2]([NH2:1])=[N:3][CH:4]=1
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참가 물질

7

반응물 3

HCID 784Hydrogen PeroxideHCID 16843TrifluoroiodomethaneHCID 5995392-Amino-5-bromopyrazine

생성물 1

HCID 717413595-Bromo-3-(trifluoromethyl)pyrazin-2-amine수율 28.9%

시약·촉매·용매 3

HCID 7611Bis(eta-cyclopentadienyl) iron촉매HCID 679Dimethyl Sulfoxide
용매
2회
HCID 57417360Sodium chloride; water용매

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온도
50 °C

실험 절차

To a solution of 2-amino-5-bromopyrazine (174 mg, 1 mmol) in DMSO (3 ml) stifling under Ar is added ferrocene (56 mg, 0.3 mmol) and degassed for 5 minutes with Ar. 2 ml of 1N H2SO4 in DMSO is added, followed by CF3I (0.276 ml, 3 mmol) in DMSO (2 ml), giving a slight yellow solution. 0.2 ml of 30% H2O2 is added slowly, causing the reaction to go from yellow to dark green in color. The reaction was heated to 50° C. for 2 hours under Ar. After cooling to room temperature, the reaction mixture is poured into brine, and product is extracted with EtOAc (4×20 ml). The combined organic fractions are dried with magnesium sulfate, filtered, then concentrated in vacuo. The crude material was purified by flash chromatography (SiO2, Biotage SNAP 10 g, 0-50% EtOAc/hept) which yields 70 mg of title compound; m/z 242.0, 244.0 (M, M+2H)

후처리

  1. customdegassed for 5 minutes with Ar
  2. addition2 ml of 1N H2SO4 in DMSO is added
  3. customgiving a slight yellow solution
  4. customthe reaction
  5. temperatureAfter cooling to room temperature
  6. extractionis extracted with EtOAc (4×20 ml)
  7. dry with materialThe combined organic fractions are dried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude material was purified by flash chromatography (SiO2, Biotage SNAP 10 g, 0-50% EtOAc/hept) which

출처 및 근거

ORD 기록
ord-502cb32e004d458eacc41558af5f2121
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08658661B2

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