Dimethyl Sulfide → HCID 67508408, compound

To a solution of 1-(4-bromo-2-fluoro-phenyl)-3-aza-bicyclo[3.1.0]hexane-2,4-dione (2.5 g, 8.8 mmol) in THF (20 mL) were added BF3.OEt2 (1.8 mL, 1.8 mmol) and BH3.Me2S (11.0 mL, 22.0 mmol) at r.t. The reaction mixture was refluxed for 3 h and progress of the reaction was monitored by TLC. On completion, the reaction mixture was quenched with 20% HCl (10 mL) and solvent evaporated, residue was washed with diethylether (10 mL). The aqueous layer was neutralized with sodium carbonate and extracted with DCM (2×20 mL). The organic layer was washed with brine (10 mL), dried over anhydrous sodium sulphate and concentrated in vacuo. The title compound was obtained as brown liquid in crude form (1.22 g, 54%) and was as such used in the next step.

1. customat r.t
2. temperatureThe reaction mixture was refluxed for 3 h
3. customOn completion, the reaction mixture was quenched with 20% HCl (10 mL) and solvent
4. customevaporated
5. washresidue was washed with diethylether (10 mL)
6. extractionextracted with DCM (2×20 mL)
7. washThe organic layer was washed with brine (10 mL)
8. dry with materialdried over anhydrous sodium sulphate
9. concentrationconcentrated in vacuo

ORD record

ord-b94657a6d2a04bfca861ce8843d3e264

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08906913B2