반응 #68948

반응 방정식

2-Amino-5-cyanopyrazine

sodium tert-butoxide

1-(4-methoxybenzyl)-6-bromo-1H-imidazo[4,5-c]pyridine

→

title compound

수율 40.0%

5-(1-(4-methoxybenzyl)-1H-imidazo[4,5-c]pyridin-6-ylamino)pyrazine-2-carbonitrile

수율 40.0%

용매

DMF toluene

반응 조건

후처리

1. 1
   기타the resulting mixture was degassed under a stream of nitrogen gas for 10 minutes
2. 2
   기타the mixture was degassed for a further 5 minutes
3. 3
   기타microwave irradiation
4. 4
   기타The reaction mixture was partitioned between water and dichloromethane
5. 5
   추출The aqueous phase extracted with dichloromethane
6. 6
   건조The combined organic layers were dried (Na2SO4)
7. 7
   농축concentrated
8. 8
   workup.DISSOLUTIONThe residue was dissolved in methanol
9. 9
   농축concentrated
10. 10
    기타The product was purified

실험 절차

Palladium (II) acetate (3.5 mg, 16 μmol) was added to (±)-2,2″-bis(diphenylphosphino)-1,1″-binaphthalene (59 mg, 94 μmol) in DMF/toluene (1:2) and the resulting mixture was degassed under a stream of nitrogen gas for 10 minutes. 2-Amino-5-cyanopyrazine (19 mg, 0.16 mmol), sodium tert-butoxide (45 mg, 0.47 mmol) and 1-(4-methoxybenzyl)-6-bromo-1H-imidazo[4,5-c]pyridine (50 mg, 0.16 mmol) were added and the mixture was degassed for a further 5 minutes before heating at 150° C. for 30 minutes using microwave irradiation. The reaction mixture was partitioned between water and dichloromethane. The aqueous phase extracted with dichloromethane. The combined organic layers were dried (Na2SO4) and concentrated. The residue was dissolved in methanol, passed through a PS-Thiol column and concentrated. The product was purified using preparative HPLC to give the title compound (22.4 mg, 40%). 1H NMR (d6-DMSO, 400 MHz) δ 10.84 (br s, 1H), 8.77 (d, 1H, J=1.3 Hz), 8.74 (m, 2H), 8.49 (s, 1H), 8.17 (s, 1H), 7.34 (m, 2H), 5.41 (s, 2H), 3.72 (s, 3H). LCMS (2) Rt=2.32 min; m/z (ESI+) 358 (MH+), (ESI−) 356 (M−H).

출처