Reaction #357320

Reaction equation

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

Solvents

EtOH

toluene

Conditions

Workup

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

Procedure

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).

Source