반응 #682997

반응 방정식

tert-butyl 3-(((trifluoromethyl)sulfonyl)oxy)-2,5-dihydro-1H-pyrrole-1-carboxylate

N2

sodium bicarbonate

potassium carbonate

5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

→

desired product

수율 78.1%

tert-butyl 3-(6-aminopyridin-3-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate

수율 78.1%

용매

THF

water

반응 조건

후처리

1. 1
   온도The reaction mixture was heated
2. 2
   추출extracted with ethyl ether
3. 3
   기타The organic layer was separated
4. 4
   세척washed with brine
5. 5
   건조dried over sodium sulfate
6. 6
   여과filtered
7. 7
   기타evaporated
8. 8
   기타The crude product was purified by flash chromatography (0-10% MeOH/DCM)

실험 절차

A solution of tert-butyl 3-(((trifluoromethyl)sulfonyl)oxy)-2,5-dihydro-1H-pyrrole-1-carboxylate (400 mg, 0.882 mmol) in THF (10 mL) was purged with N2 for 5 min and then was added potassium carbonate (610 mg, 4.41 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (233 mg, 1.059 mmol), Pd(PPh3)4 (10.20 mg, 8.82 μmol) and water (0.1 mL). The reaction mixture was heated and stirred at 70° C. overnight. The reaction mixture was poured to saturated sodium bicarbonate solution and extracted with ethyl ether. The organic layer was separated, washed with brine, dried over sodium sulfate, filtered and evaporated. The crude product was purified by flash chromatography (0-10% MeOH/DCM) to yield the desired product (180 mg, 54.6%). LCMS (m/z): 262.2 (MH+), 0.598 min.

출처