반응 #1834514

반응 방정식

water

3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionitrile

azidotrimethylsilane

dibutyltin oxide

azidotrimethylsilane

dibutyltin oxide

→

1-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-3-[2-(1H-tetrazol-5-yl)-ethyl]-1,3-dihydro-benzimidazol-2-one

수율 65.0%

용매

DMF

반응 조건

후처리

1. 1
   온도the mixture is heated for another 2 hr at 150° C. in microwave reactor
2. 2
   추출the mixture is extracted with EtOAc (2×30 mL)
3. 3
   추출extracted with 2.0M NaOH (2×30 mL)
4. 4
   세척washed with EtOAc (30 mL)
5. 5
   추출is then extracted with EtOAc (2×30 mL)
6. 6
   건조dried (MgSO4)
7. 7
   농축concentrated
8. 8
   기타to give crude product
9. 9
   기타Purification by preparative TLC

실험 절차

3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionitrile (58 mg, 0.17 mmol), azidotrimethylsilane (0.047 mL, 0.33 mmol) and dibutyltin oxide (4.2 mg, 0.017 mmol) are dissolved in dry DMF (2.0 mL) in microwave vial. It is then heated at 150° C. for 2 hrs in microwave reactor. Then another 0.05 mL of azidotrimethylsilane and 4.0 mg of dibutyltin oxide are added and the mixture is heated for another 2 hr at 150° C. in microwave reactor. Then water (2 mL) is added and the mixture is extracted with EtOAc (2×30 mL). The organic layers are combined and extracted with 2.0M NaOH (2×30 mL). The NaOH layers are combined and washed with EtOAc (30 mL). Then the NaOH layers are acidified with 1.0M HCl to pH=3 and it is then extracted with EtOAc (2×30 mL). All the organic layers are combined, dried (MgSO4) and concentrated to give crude product. Purification by preparative TLC using 3% MeOH in CH2Cl2 affords 15 mg (65%) of 1-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-3-[2-(1H-tetrazol-5-yl)-ethyl]-1,3-dihydro-benzimidazol-2-one. LCMS (ESMS): m/z 391.07 (M+H+).

출처