Methyl iodide → HCID 57691376, compound

Temperature

-78 °C

To a flame-dry 100 ml 3-neck round-bottomed flask was added lithium bis(trimethylsilyl)amide, 1.0 m solution in tetrahydrofuran (5 ml, 5 mmol) and THF (20 mL). The mixture was cooled to −78° C. followed by adding tert-butyl 2-(3-methoxyquinolin-6-yl)acetate (0.88 g, 3 mmol) in THF (10 mL)dropwise via addition funnel. After stirring at −78° C. for 30 min, iodomethane (0.4 ml, 6 mmol) was added. The reaction mixture was stirred for 30 min at −78° C. then allowed to warm to rt and stir for 1 h. The mixture was then quenched with sat. NH4Cl (3 mL). Solvent was removed. The residue was partitioned between EtOAc/water. The organic layer was washed with brine, dried over MgSO4 and removed solvent. The crude material was purified using SiO2 chromatography (Teledyne Isco RediSep®, P/N 68-2203-027, 40 g SiO2, solvent system: hexane:acetone=90%:10%, Flow=30 mL/min) to afford a final product as yellowish liquid. MS m/z: 288.4 (M+H). Calc'd. for C17H21NO3—287.3.

1. additiondropwise via addition funnel
2. stirringThe reaction mixture was stirred for 30 min at −78° C.
3. temperatureto warm to rt
4. stirringstir for 1 h
5. customThe mixture was then quenched with sat. NH4Cl (3 mL)
6. customSolvent was removed
7. customThe residue was partitioned between EtOAc/water
8. washThe organic layer was washed with brine
9. dry with materialdried over MgSO4
10. customremoved solvent
11. customThe crude material was purified

ORD record

ord-9fe49d7250de4beeba7e7660e2ae2063

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08524900B2