Triethylamine → HCID 86732184, compound

Temperature

80 °C

A solution of 1-(5-bromo-2-fluoropyridin-3-yl)ethanone (200 mg, 0.92 mmol) and triethylamine (140 μl, 1.01 mmol) in toluene (2 mL) was treated with trimethylsilyl trifluoromethanesulfonate (182 μl, 1.01 mmol) under nitrogen atmosphere. The reaction mixture was heated to 80° C. for 2 h, the upper toluene phase was isolated (e.g. by decanting) and concentrated under reduced pressure to give a yellow oil. The oil was dissolved in acetonitrile (2 mL) and added to a suspension of 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo-(2.2.2)octane bis(tetrafluoroborate) (325 mg, 0.92 mmol) in acetonitrile (2 mL) at room temperature. After 1 h, the solvent was removed under reduced pressure. The residue was partitioned between brine and EtOAc. The organic phase was separated and dried over MgSO4. The solvent was removed under reduced pressure to obtain 1-(5-bromo-2-fluoropyridin-3-yl)-2-fluoroethanone (170 mg, 0.72 mmol, 79% yield, 90% purity) as a light yellow solid. This material was used in the next step without purification. MS m/z=237.9 [M+H]+. Calculated for C7H4BrF2NO: 236.01.

1. custom(e.g. by decanting)
2. concentrationconcentrated under reduced pressure
3. customto give a yellow oil
4. customthe solvent was removed under reduced pressure
5. customThe residue was partitioned between brine and EtOAc
6. customThe organic phase was separated
7. dry with materialdried over MgSO4
8. customThe solvent was removed under reduced pressure

ORD record

ord-5e00462d1f174214aadc0de0f3c5c694

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09296734B2