Potassium Carbonate → 4-Methoxy-2-(4-methyl-thiazol-2-yl)-6-(4-trifluoromethyl-thiazol-2-yl)-pyridine

HRID 530756Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 530756
Cl[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([C:10]2[S:11][CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:14]=2)[N:3]=1.[CH3:19][C:20]1[N:21]=[C:22]([Sn](CCCC)(CCCC)CCCC)[S:23][CH:24]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:9][O:8][C:6]1[CH:5]=[C:4]([C:10]2[S:11][CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:14]=2)[N:3]=[C:2]([C:22]2[S:23][CH:24]=[C:20]([CH3:19])[N:21]=2)[CH:7]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 164271304-Methyl-2-(tributylstannyl)-1,3-thiazoleHCID 866691142-Chloro-4-methoxy-6-(4-trifluoromethyl-thiazol-2-yl)-pyridine

Produkt 1

HCID 681599974-Methoxy-2-(4-methyl-thiazol-2-yl)-6-(4-trifluoromethyl-thiazol-2-yl)-pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution of compound 21 (4.17 mmol) in DMF (15 mL) were added 4-methyl-2-(tributylstannyl)thiazole (5 mmol), dichlorobis(triphenylphosphine) palladium (II) chloride (0.417 mmol), and K2CO3 (5 mmol). The reaction mixture was stirred at 110° C. under microwave irradiations for 1 hr. The solution was concentrated in vacuo and H2O and DCM were added. The layers were separated and the organic layer was concentrated. The crude was purified by silica gel chromatography (eluent: DCM) to give compound 22 in quantitative yield. MS (ESI, EI+): m/z=357.87 (MH+).

Aufarbeitung

  1. concentrationThe solution was concentrated in vacuo and H2O and DCM
  2. additionwere added
  3. customThe layers were separated
  4. concentrationthe organic layer was concentrated
  5. customThe crude was purified by silica gel chromatography (eluent: DCM)

Quellen und Nachweise

ORD-Eintrag
ord-c1d5bf4eb9464ffeb9bf13fd7ee9b79f
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353100B2

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