Reacción #357320

Ecuación de reacción

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

Disolventes

EtOH

toluene

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente