Water → 6-methyl-1-tosyl-1H-pyrrolo[2,3-b]pyridine

HRID 1749809노트

반응식

HRID 1749809 반응식
Cl[C:2]1[N:7]=[C:6]2[N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1.[Cl-].[CH3:22][Zn+].O>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:22][C:2]1[N:7]=[C:6]2[N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 962WaterHCID 862804116-Chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 178477797HCID 178477797, 화합물

생성물 1

HCID 712789696-methyl-1-tosyl-1H-pyrrolo[2,3-b]pyridine수율 81%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매2회

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온도
60 °C

실험 절차

The synthesis was performed with reference to the known literature (US 2006/0148801). A solution of 6-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine (0.38 g, 1.2 mmol) in tetrahydrofuran (20 mL) was added with tetrakis(triphenylphosphine)palladium(0) (0.069 g, 0.060 mmol) under an argon atmosphere. Then, the mixture was added dropwise with a 2 M solution of methyl zinc chloride in THF (3.6 mL, 7.2 mmol), and then the mixture was stirred at 60° C. for 48 hours. The reaction mixture was added with water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and then the residue was subjected to silica gel column chromatography (eluted with hexane/ethyl acetate (90:10→50:50)) to obtain 6-methyl-1-tosyl-1H-pyrrolo[2,3-b]pyridine (0.28 g, 81%).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washthe residue was subjected to silica gel column chromatography (eluted with hexane/ethyl acetate (90:10→50:50))

출처 및 근거

ORD 기록
ord-0217df0107584c8e92778129f8205e06
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156827B2

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