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Sodium Carbonate → Trimethyl-[2-[[6-(5-vinyl-3-pyridyl)pyrazolo[4,3-c]pyridin-1-yl]methoxy]ethyl]silane

HRID 57826
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HRID 57826 반응식
Cl[C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][N:10]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:4]=2[CH:3]=1.CC1(C)C(C)(C)OB([C:27]2[CH:28]=[N:29][CH:30]=[C:31]([CH:33]=[CH2:34])[CH:32]=2)O1.C([O-])(=O)C.[K+].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl>[CH3:16][Si:15]([CH3:18])([CH3:17])[CH2:14][CH2:13][O:12][CH2:11][N:10]1[C:4]2[CH:3]=[C:2]([C:27]3[CH:28]=[N:29][CH:30]=[C:31]([CH:33]=[CH2:34])[CH:32]=3)[N:7]=[CH:6][C:5]=2[CH:8]=[N:9]1
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참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 867070302-[(6-Chloropyrazolo[4,3-c]pyridin-1-yl)methoxy]ethyl-trimethyl-silaneHCID 867070323-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-5-vinylpyridine

생성물 1

HCID 86707031Trimethyl-[2-[[6-(5-vinyl-3-pyridyl)pyrazolo[4,3-c]pyridin-1-yl]methoxy]ethyl]silane수율 143.5%

시약·촉매·용매 2

HCID 178418807HCID 178418807, 화합물촉매HCID 6342Acetonitrile용매

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온도
150 °C

실험 절차

A mixture of 2-[(6-chloropyrazolo[4,3-c]pyridin-1-yl)methoxy]ethyl-trimethyl-silane (1.074 mmol; 304.8 mg), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-vinyl-pyridine (1.611 mmol; 372.3 mg), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (0.1074 mmol; 89.5 mg), potassium acetate (1.611 mmol; 1.6 mL) and sodium carbonate (1.611 mmol; 1.6 mL) in Acetonitrile (10 mL) in a pressure tube was heated under microwave at 150° C. for 5 min. The mixture was cooled to room temperature. The layers were separated. The aqueous layer was extracted with EtOAc. The combined organic layer was concentrated. The residue was purified on silica eluted with 0 to 6% MeOH in DCM to afford trimethyl-[2-[[6-(5-vinyl-3-pyridyl)pyrazolo[4,3-c]pyridin-1-yl]methoxy]ethyl]silane (543.4 mg, 86%).

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. customThe layers were separated
  3. extractionThe aqueous layer was extracted with EtOAc
  4. concentrationThe combined organic layer was concentrated
  5. customThe residue was purified on silica
  6. washeluted with 0 to 6% MeOH in DCM

출처 및 근거

ORD 기록
ord-590b3cf8006645918e3321c7a7a891b4
출처 데이터셋
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09434725B2

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