반응 #331766

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2-amino-5-bromopyrazine

H2O2

CF3I

→

title compound

수율 28.9%

5-Bromo-3-trifluoromethyl-pyrazin-2-ylamine

수율 28.9%

용매

DMSO

DMSO

brine

반응 조건

후처리

1. 1
   기타degassed for 5 minutes with Ar
2. 2
   workup.ADDITION2 ml of 1N H2SO4 in DMSO is added
3. 3
   기타giving a slight yellow solution
4. 4
   기타the reaction
5. 5
   온도After cooling to room temperature
6. 6
   추출is extracted with EtOAc (4×20 ml)
7. 7
   건조The combined organic fractions are dried with magnesium sulfate
8. 8
   여과filtered
9. 9
   농축concentrated in vacuo
10. 10
    기타The crude material was purified by flash chromatography (SiO2, Biotage SNAP 10 g, 0-50% EtOAc/hept) which

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)

출처