Methyl iodide → 7,8,9,10-Tetrahydro-2,3-dimethoxy-6,8-dimethyl-pyrido[4,3-f]quinoxaline

Temperature

-78 °C

A solution of the product from Example 100 (0.50 g, 1.48 mol) in 20 mL of tetrahydrofuran was cooled to −78° C. and treated dropwise with sec-BuLi (1.7 mL, 1.17 M in cyclohexane). The resulting green-black solution was stirred at −78° C. for 30 minutes. The reaction mixture was treated with MeI (123 μL, 2.00 mmol) and the resulting solution stirred at −78° C. for 30 minutes. The reaction mixture was warmed to room temperature and quenched with saturated aqueous NH4Cl solution (2.0 mL). The reaction mixture was extracted with CHCl3 (4×20 mL) and the combined organic extracts were dried and concentrated. The residue was broken up in heptane and collected by suction filtration to give the title compound as a orange solid (0.196 g, 48% yield).

1. stirringthe resulting solution stirred at −78° C. for 30 minutes
2. temperatureThe reaction mixture was warmed to room temperature
3. customquenched with saturated aqueous NH4Cl solution (2.0 mL)
4. extractionThe reaction mixture was extracted with CHCl3 (4×20 mL)
5. customthe combined organic extracts were dried
6. concentrationconcentrated
7. filtrationcollected by suction filtration

ORD record

ord-02eb257edce74edda79b5c69318ebc6e

Source dataset

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06703391B2