Acetonitrile → 5-Bromo-2-[2-(2-(R)-methyl-pyrrolidin-1-yl)-ethyl]-benzothiazole

A solution of 2-(5-bromo-benzothiazol-2-yl)-ethanol (1.50 g, 5.8 mmol) and triethylamine (1.33 g, 11.6 mmol) in CH2Cl2 was cooled to 0° C., and mesyl chloride was added dropwise. The mixture was warmed to room temperature and stirred for 1 hr. The solvent was removed under vacuum, and to the residue was added acetonitrile (20 mL), triethylamine (1.33 g, 11.6 mmol) 2-(R)-methylpyrrolidine hydrochloride (2.83 g, 23.2 mmol) to the mixture, and the mixture was stirred at 60° C. for 1 hr. Solvents were removed under vacuum, and the residue was dissolved in 20 mL methylene chloride and washed with 10 mL water. The aqueous layer was re-extracted with 10 mL methylene chloride. The combined methylene chloride extracts were concentrated to give a crude product yield 1.9 g (100%)

1. customThe solvent was removed under vacuum
2. stirringthe mixture was stirred at 60° C. for 1 hr
3. customSolvents were removed under vacuum
4. dissolutionthe residue was dissolved in 20 mL methylene chloride
5. washwashed with 10 mL water
6. extractionThe aqueous layer was re-extracted with 10 mL methylene chloride
7. concentrationThe combined methylene chloride extracts were concentrated

ORD record

ord-648115ee2be148f0b50d9bf80b823d53

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07094790B2