反応 #357320

反応方程式

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

溶媒

EtOH

toluene

反応条件

後処理

1. 1
   その他argon was bubbled through the solution while the other reagents
2. 2
   workup.ADDITIONwere added
3. 3
   その他The vessel was sealed
4. 4
   温度the reaction heated to 100° overnight
5. 5
   その他The reaction mixture was partitioned between 5% NaHCO3 and EtOAc
6. 6
   抽出extracted several times with EtOAc
7. 7
   洗浄The combined organic layers were washed with brine
8. 8
   乾燥dried over MgSO4
9. 9
   ろ過filtered
10. 10
    その他evaporated
11. 11
    その他The crude product was chromatographed on silica gel (chromatotron, eluting with 1-4% MeOH/CH2Cl2)

実験手順

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).

出典