Cesium carbonate → 5-Methoxy-3-((triethylsilyl)ethynyl)picolinonitrile

HRID 930480노트

반응식

HRID 930480 반응식
[C:1](=[O:4])([O-])[O-].[Cs+].[Cs+].Cl[C:8]1[C:9]2[N:17]=[CH:16][C:15](Cl)=[CH:14][C:10]=2N=C[N:13]=1.[CH2:19]([Si:21]([CH2:26][CH3:27])([CH2:24][CH3:25])[C:22]#[CH:23])[CH3:20]>CC#N.CC#N.Cl[Pd]Cl.C(#N)C>[CH3:1][O:4][C:15]1[CH:14]=[C:10]([C:20]#[C:19][Si:21]([CH2:26][CH3:27])([CH2:24][CH3:25])[CH2:22][CH3:23])[C:9]([C:8]#[N:13])=[N:17][CH:16]=1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 637947(Triethylsilyl)acetyleneHCID 714284454,7-Dichloropyrido[3,2-d]pyrimidine

생성물 1

HCID 867322855-Methoxy-3-((triethylsilyl)ethynyl)picolinonitrile

시약·촉매·용매 2

HCID 6093782Bis(acetonitrile)dichloropalladium촉매HCID 6342Acetonitrile용매

실험 절차

A sealable vessel was charged with bis(acetonitrile)palladium (II) chloride (0.154 g, 0.593 mmol), dicyclohexyl(2′,4′,6′-triisopropyl-[1′,1′-biphenyl]-2-yl)phosphine (0.848 g, 1.780 mmol), cesium carbonate (25.1 g, 77 mmol), the product of Intermediate 9, step 1 (5 g, 29.7 mmol), and ACN (60 mL). The vessel was flushed with argon, sealed, and stirred at RT for 25 minutes. To the reaction was added triethyl(ethynyl)silane (5.41 g, 38.6 mmol), and the vessel was resealed and stirred at 90° C. for 3 hours. The solution was concentrated, and the residue was purified via silica gel chromatography, eluting with 0-50% ethyl acetate in heptanes, to afford the title compound (3.8 g, 13.9 mmol). MS m/z=273 (M+H).

후처리

  1. customThe vessel was flushed with argon
  2. customsealed
  3. stirringstirred at 90° C. for 3 hours
  4. concentrationThe solution was concentrated
  5. customthe residue was purified via silica gel chromatography
  6. washeluting with 0-50% ethyl acetate in heptanes

출처 및 근거

ORD 기록
ord-fd564755e9af4be9b2856be807f7b99d
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296734B2

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