Toluene → 2-Bromo-6-(2-pyridin-3-yl-thiazol-5-yl)-pyridine

HRID 1854620Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1854620
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.C([Sn](CCCC)(CCCC)[C:14]1[S:18][C:17]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[N:16][CH:15]=1)CCC.C(Cl)Cl.C1(C)C=CC=CC=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[Br:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:14]2[S:18][C:17]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)=[N:16][CH:15]=2)[N:3]=1

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 6344DichloromethaneHCID 122742,6-DibromopyridineHCID 673254043-(5-Tributylstannanyl-thiazol-2-yl)-pyridine

Produkt 1

HCID 533113132-Bromo-6-(2-pyridin-3-yl-thiazol-5-yl)-pyridineAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A sealed tube was charged with 2,6-dibromopyridine (269 mg, 1.13 mmol), 3-(5-tributylstannanyl-thiazol-2-yl)-pyridine (511 mg, 1.13 mmol), Pd(PPh3)4 (131 mg, 0.11 mmol), [1,1-Bis(diphenylphosphino)ferrocene]palladium(II) chloride. CH2Cl2 (20 mg, 0.024 mmol) and anhydrous and degassed toluene (5 ml) and heated to 110° C. with stirring for 36 h. The cooled reaction mixture was treated with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered and evaporated under reduced pressure before purification by column chromatography on SiO2 using combiflash Companion®, eluting with cyclohexane/ethyl acetate to afford the title compound as a white solid (125 mg, 35%). 1H NMR (DMSO-d6, 300 MHz): δ=9.21 (d, J=1.7 Hz, 1H), 8.72 (s, 1H), 8.70 (m, 1H), 8.39 (m, 1H), 8.14 (d, J=7.8 Hz, 1H), 7.88 (dd, J=8.0; 7.8 Hz, 1H), 7.62 (d, J=8.0 Hz, 1H), 7.57 (m, 1H).

Aufarbeitung

  1. customThe cooled reaction mixture
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure before purification by column chromatography on SiO2 using combiflash Companion®
  7. washeluting with cyclohexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-e66f448996fb4263bc92e301dadb0978
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962665B2

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