N-Fluorobenzenesulfonimide → Methyl 2-fluoro-2-(quinolin-6-yl)acetate

Temperature

-78 °C

To a 250 ml round-bottomed flask was added lithium bis(trimethylsilyl)amide (2.0 g, 12 mmol) and tetrahydrofuran (75 ml). The mixture was cooled to −78° C. and methyl 2-(quinolin-6-yl)acetate (2.0 g, 9.9 mmol) was added as a solution in 1 ml THF. After stirring at −78° C. for 30 min, n-fluorobenzenesulfonimide (3.8 g, 12 mmol) was added as a 1M solution in THF. This was stirred for 30 min at −78° C. and then allowed to warm to rt. The mixture was quenched with sat NH4Cl (50 mL) and diluted with water (200 mL). The mixture was concentrated in vacuo to remove the THF and then was extracted with EtOAc (2×100 ml). The combined extracts were washed with brine (100 ml), dried (Na2SO4) and concentrated onto silica. Purification by silica gel chromatography (20 to 60% EtOAc/hexane) afforded the title compound as a tan solid. MS (ESI, pos. ion) m/z: 220 (M+1).

1. stirringThis was stirred for 30 min at −78° C.
2. temperatureto warm to rt
3. customThe mixture was quenched with sat NH4Cl (50 mL)
4. additiondiluted with water (200 mL)
5. concentrationThe mixture was concentrated in vacuo
6. customto remove the THF
7. extractionwas extracted with EtOAc (2×100 ml)
8. washThe combined extracts were washed with brine (100 ml)
9. dry with materialdried (Na2SO4)
10. concentrationconcentrated onto silica
11. customPurification by silica gel chromatography (20 to 60% EtOAc/hexane)

ORD record

ord-18b9de51a4964c86a982b083a0c46265

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08198448B2