Sodium Carbonate → 5-(2-Chloropyrimidin-4-yl)thiophene-2-carbonitrile

HRID 507581

Reaktionsgleichung

Reaktionsgleichung von HRID 507581
[C:1]([C:3]1[S:7][C:6](B(O)O)=[CH:5][CH:4]=1)#[N:2].[Cl:11][C:12]1[N:17]=[C:16](Cl)[CH:15]=[CH:14][N:13]=1.C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1>C(Cl)Cl.CO.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:11][C:12]1[N:17]=[C:16]([C:6]2[S:7][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH:15]=[CH:14][N:13]=1

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 775312,4-DichloropyrimidineHCID 41987435-Cyanothiophene-2-boronic acid

Produkt 1

HCID 574288365-(2-Chloropyrimidin-4-yl)thiophene-2-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A solution of 0.22 g (1.4 mmol) of 5-cyanothiophen-2-ylboronic acid, 0.21 g (1.4 mmol) of 2,4-dichloropyrimidine and 49 mg (0.070 mmol) of bis(triphenylphosphine)palladium(II) chloride in 2 mL of a 2 M Na2CO3 aqueous solution and 5 mL of 1,4-dioxane was as heated in a microwave for 30 min at 140° C., then cooled to rt, diluted with CH2Cl2 and MeOH, and dried over MgSO4. The organic solvent was removed in vacuo, and the resulting solid was purified by flash chromatography eluting with a linear gradient of 50% EtOAc in hexane to neat EtOAc to deliver the title compound. MS (M+H)+ 222.

Aufarbeitung

  1. temperaturecooled to rt
  2. dry with materialdried over MgSO4
  3. customThe organic solvent was removed in vacuo
  4. customthe resulting solid was purified by flash chromatography
  5. washeluting with a linear gradient of 50% EtOAc in hexane to neat EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-162f32b7cb2544d4b2a85e2fd1078312
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786132B2

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