반응 #88666

반응 방정식

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate

4-bromo-N2-methylbenzene-1,2-diamine

diisopropylethylamine

(1RS,2SR)-2-(methoxycarbonyl)cyclopropanecarboxylic acid

→

title compound

수율 18.6%

Methyl (1RS,2SR)-2-(6-bromo-1-methyl-1H-benzimidazol-2-yl)cyclopropanecarboxylate

수율 18.6%

용매

Water

DMF

반응 조건

후처리

1. 1
   추출the mixture was extracted with ethyl acetate
2. 2
   세척The obtained organic layer was washed with water and brine
3. 3
   건조dried over magnesium sulfate
4. 4
   농축concentrated in vacuo
5. 5
   workup.DISSOLUTIONThe obtained residue was dissolved in acetic acid (5 mL)
6. 6
   workup.STIRRINGthe mixture was stirred at 80° C. for 1 hr
7. 7
   workup.ADDITIONAfter concentration of the reaction mixture, saturated sodium hydrogen carbonate was added to the residue
8. 8
   추출the mixture was extracted with ethyl acetate
9. 9
   세척The obtained organic layer was washed with water and brine
10. 10
    건조dried over magnesium sulfate
11. 11
    농축concentrated in vacuo
12. 12
    기타The obtained residue was purified by silica gel column chromatography (methanol/ethyl acetate)

실험 절차

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (554 mg) was added to a solution of 4-bromo-N2-methylbenzene-1,2-diamine (279 mg), diisopropylethylamine (0.727 mL) and (1RS,2SR)-2-(methoxycarbonyl)cyclopropanecarboxylic acid (200 mg) in DMF (5 mL) at room temperature. The mixture was stirred for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. The obtained residue was dissolved in acetic acid (5 mL), and the mixture was stirred at 80° C. for 1 hr. After concentration of the reaction mixture, saturated sodium hydrogen carbonate was added to the residue, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. The obtained residue was purified by silica gel column chromatography (methanol/ethyl acetate) to give the title compound (80 mg) as a pale brown solid.

출처