Diisopropylamine → HCID 67432976, Verbindung

Temperatur

-78 °C

According to Scheme 16: Butyl lithium 2.5 M (9.9 mmol, 4 mL) was added to a solution of diisopropylamine (9.9 mmol, 1.4 mL) in THF (20 mL) at −78° C. and the reaction mixture was stirred at −78° C. for 5 minutes and then at room temperature. To the resulting LDA solution was added at −78° C. a solution of ethyl 1-(4-methoxybenzyl)-1H-pyrazole-4-carboxylate (7.61 mmol, 1.98 g) in THF (30 mL) and the reaction mixture was stirred for 15 minutes at −78° C. Then N-methoxy-N-methylcyclopropanecarboxamide (9.14 mmol, 1.18 g) in THF (10 mL) was added and the reaction mixture was stirred at room temperature. The reaction mixture was diluted with AcOEt and washed with a saturated aqueous solution of NH4Cl. The combined organic phases were dried over MgSO4, were filtered and solvents were evaporated. The crude mixture was purified by flash chromatography over silica gel using cyclohexane/AcOEt (90:10) as eluent to yield ethyl 3-(cyclopropanecarbonyl)-1-(4-methoxybenzyl)-1H-pyrazole-4-carboxylate (0.74 mmol, 244 mg, 9%).

1. customat room temperature
2. stirringthe reaction mixture was stirred for 15 minutes at −78° C
3. stirringthe reaction mixture was stirred at room temperature
4. washwashed with a saturated aqueous solution of NH4Cl
5. dry with materialThe combined organic phases were dried over MgSO4
6. filtrationwere filtered
7. customsolvents were evaporated
8. customThe crude mixture was purified by flash chromatography over silica gel

ORD-Eintrag

ord-a7f3b950de5941e197810b8613707ade

Quelldatensatz

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09073907B2