Water → 2-Methyl-6,7-dihydro-8H-indeno[5,4-d]thiazol-8-one

Temperature

60 °C

6-Amino-7-iodoindan-1-one (1.00 g, 3.66 mmol), thioacetamide (413 mg, 5.49 mmol), 1,1′-bis(diphenylphosphino)ferrocene (383 mg, 1.46 mmol), calcium oxide (411 mg, 7.32 mmol) and tris(dibenzylideneacetone)dipalladium(0) (335 mg, 0.37 mmol) were dissolved in N,N-dimethylformamide (12 mL), and the mixture was stirred at 60° C. for 1 hr. After allowing to cool to room temperature, water was added to the reaction solution. The mixture was extracted with ethyl acetate and washed with saturated brine. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=25/75→65/35), and then purified by silica gel column chromatography (NH, ethyl acetate/hexane=10/90→40/60) to give the title compound (340 mg, yield 46%).

1. temperatureto cool to room temperature
2. extractionThe mixture was extracted with ethyl acetate
3. washwashed with saturated brine
4. customThe solvent was evaporated under reduced pressure
5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=25/75→65/35)
6. custompurified by silica gel column chromatography (NH, ethyl acetate/hexane=10/90→40/60)

ORD record

ord-b355120808384d0aa319f388a916c293

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08030337B2