Reaktion #357320

Reaktionsgleichung

water

4-(2-tert-Butyl-5-iodo-3-H-imidazol-4-yl)-pyridine

1-naphthyl boronic acid

NaHCO3

→

title compound

2-tert-Butyl-4-naphthalen-2-yl-5-pyridin-4-yl-imidazole

Lösungsmittel

EtOH

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeargon was bubbled through the solution while the other reagents
2. 2
   workup.ADDITIONwere added
3. 3
   SonstigeThe vessel was sealed
4. 4
   Temperaturthe reaction heated to 100° overnight
5. 5
   SonstigeThe reaction mixture was partitioned between 5% NaHCO3 and EtOAc
6. 6
   Extraktionextracted several times with EtOAc
7. 7
   WaschenThe combined organic layers were washed with brine
8. 8
   Trocknendried over MgSO4
9. 9
   Filtrationfiltered
10. 10
    Sonstigeevaporated
11. 11
    SonstigeThe crude product was chromatographed on silica gel (chromatotron, eluting with 1-4% MeOH/CH2Cl2)

Vorschrift

In a heavy-walled pressure vessel 4-(2-tert-Butyl-5-iodo-3-H-imidazol-4-yl)-pyridine (100 milligrams (hereinafter “mg”), 0.3 mmol) and tetrakis-triphenylphosphine palladium (0) catalyst was dissolved in toluene (2-3 ml) and argon was bubbled through the solution while the other reagents were added: 1-naphthyl boronic acid (86 mg, 0.5 mmol), solid NaHCO3 (84 mg), water (500 uL), EtOH (500 uL). The vessel was sealed and the reaction heated to 100° overnight. The reaction mixture was partitioned between 5% NaHCO3 and EtOAc and extracted several times with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered, and evaporated. The crude product was chromatographed on silica gel (chromatotron, eluting with 1-4% MeOH/CH2Cl2) to give the title compound as a yellow solid. (58 mg, 59%). mp 218-220°; MS m/e: 328 [M+H]+, 326 [M−H]−; 1H NMR(400 MHz, CDCl3) δ 9.63(br s, 1H), 8.16(app d, J=4.8 Hz, 2H), 7.92(br d, J=8.3 Hz, 2H), 7.64 (br d, 1H), 7.52 (m, 3H), 7.41 (t, J=6 Hz, 1H), 7.29 (br s, 2H), 1.49 (s, 9H).

Quelle