Sodium Bicarbonate → HCID 59540958, 화합물

HRID 1677513

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HRID 1677513 반응식
[Cl-].C([Al+]CC)C.[Br:7][C:8]1[N:9]=[C:10]2[CH:16]=[CH:15][NH:14][C:11]2=[N:12][CH:13]=1.[CH3:17][C:18]([CH3:25])([CH2:22][CH:23]=[CH2:24])[C:19](Cl)=[O:20].C([O-])(O)=O.[Na+]>ClCCl>[Br:7][C:8]1[N:9]=[C:10]2[C:16]([C:19](=[O:20])[C:18]([CH3:25])([CH3:17])[CH2:22][CH:23]=[CH2:24])=[CH:15][NH:14][C:11]2=[N:12][CH:13]=1

참가 물질

6

반응물 4

HCID 516892Sodium BicarbonateHCID 110735602,2-Dimethyl-4-pentenoyl chlorideHCID 16686102Diethyl aluminum chlorideHCID 250673082-bromo-5H-pyrrolo[2,3-b]pyrazine

생성물 1

HCID 59540958HCID 59540958, 화합물수율 43%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
2.5 °C

실험 절차

Diethylaluminum chloride (1.0 M in CH2Cl2, 23.4 mL, 23.4 mmol) was added to a 0-5° C. mixture of 2-bromo-5H-pyrrolo[2,3-b]pyrazine (1.55 g, 7.80 mmol) and 30 mL of dichloromethane in a sealed tube, and the mixture was stirred at 0-5° C. for 20 min. The solution of crude 2,2-dimethyl-4-pentenoyl chloride prepared in the previous step was added dropwise. The resulting mixture was stirred at 60° C. for 64 h, then cooled to 0-5° C. A sat. aq. NaHCO3 solution (50 mL) was carefully added, and the mixture was extracted with three 100 mL portions of ethyl acetate. The combined organic layers were dried over MgSO4, filtered and concentrated to a residue. Column chromatography (0→50% EtOAc/hexanes) afforded 1.033 g (43%) of impure 1-(2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethyl-pent-4-en-1-one as a brown solid, which was used without further purification. The major impurity is s.m. (typically 15-30% of the mixture).

후처리

  1. additionwas added dropwise
  2. stirringThe resulting mixture was stirred at 60° C. for 64 h
  3. temperaturecooled to 0-5° C
  4. extractionthe mixture was extracted with three 100 mL portions of ethyl acetate
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to a residue

출처 및 근거

ORD 기록
ord-223468fec13a435980aeff76d065aeb0
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008298B2

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