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

HRID 930480ノート

反応式

HRID 930480 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6093782Bis(acetonitrile)dichloropalladium触媒HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fd564755e9af4be9b2856be807f7b99d
出典データセット
uspto-grants-2016_03
特許番号
US09296734B2

反応ノート

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