1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 66957609, compound

Temperature

200 °C

A mixture of 5-trifluoromethoxy-benzo[b]thiophene-2-carboxylic acid (2.00 g, 7.63 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (5.0 mL, 32 mmol) in DMA (12 mL) was heated via microwave irradiation at 200° C. for 1 h. The reaction was cooled to rt, diluted with HCl (1 N aq., 15 mL) and extracted with EtOAc (15 mL). The organic layer was washed with water (10 mL), dried (Na2SO4) and concentrated. The residue was taken up in Et2O (25 mL) and washed with water (25 mL). The aqueous layer was extracted with Et2O (10 mL×2). The combined Et2O layers were dried (Na2SO4) and concentrated. The crude material was purified (FCC) to yield the title compound (518 mg, 31%).

1. temperatureThe reaction was cooled to rt
2. extractionextracted with EtOAc (15 mL)
3. washThe organic layer was washed with water (10 mL)
4. dry with materialdried (Na2SO4)
5. concentrationconcentrated
6. washwashed with water (25 mL)
7. extractionThe aqueous layer was extracted with Et2O (10 mL×2)
8. dry with materialThe combined Et2O layers were dried (Na2SO4)
9. concentrationconcentrated
10. customThe crude material was purified (FCC)

ORD record

ord-d180ea735f864f20b160e552c1370791

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08906914B2