Potassium Iodide → 4-[2-(3-Chloro-benzylamino)-quinoxalin-6-yl]-pyrazole-1-carboxylic acid tert-butyl ester

온도

110 °C

A mixture of (6-Bromo-quinoxalin-2-yl)-(3-chloro-benzyl)-amine (0.4 g, 1 eq., 1.15 mmol), 1-Boc-4-pyrazole boronic acid pinacol ester (0.4 g, 1.2 eq., 1.37 mmol), caesium carbonate (1.5 g, 4.0 eq., 4.6 mmol) and potassium iodide (0.019 g, 0.1 eq., 0.11 mmol) in 1,4-dioxane (22 mL) was degassed at RT under vacuum and then placed under an atmosphere of nitrogen. The process was repeated twice and Fu's catalyst (Bis(tri-tert-butylphosphine)palladium(0)) (0.058 g, 0.1 eq., 0.1 mmol) was added at room temperature. The reaction mixture was heated to 110° C. in a microwave reactor for 180 minutes. After completion of the reaction (confirmed by TLC), the organic mixture was diluted with ethyl acetate (200 mL) and washed with water (75 mL×3) then brine (75 mL). The organic layer was dried and concentrated to afford the crude product.

1. customwas degassed at RT under vacuum
2. additionFu's catalyst (Bis(tri-tert-butylphosphine)palladium(0)) (0.058 g, 0.1 eq., 0.1 mmol) was added at room temperature
3. customAfter completion of the reaction (confirmed by TLC)
4. washwashed with water (75 mL×3)
5. customThe organic layer was dried
6. concentrationconcentrated

ORD 기록

ord-5663f36a1df5460085686f618c0961d6

출처 데이터셋

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08716473B2