HCID 67378916, compound → HCID 67378877, compound

Temperature

80 °C

To a solution of 2-(pyridin-4-yl)-2H-benzo[b][1,4]thiazin-3(4H)-one (0.6 g, 0.00247 mol) in THF (60 mL) was added borane-dimethyl sulfide complex solution under nitrogen atmosphere. The reaction mixture was heated at 80° C. for 3 h. After completion of reaction (monitored by TLC), the reaction mixture was cooled to RT and quenched with 1N hydrochloric acid (100 mL). The mixture was then basified with 10% sodium hydroxide solution (50 mL), extracted with EtOAc (3×100 mL), and the organic layer concentrated under reduced pressure. The crude product was purified by column chromatography (70% EtOAc:hexane in silica 100-200 mesh, diameter of column—5 cm, height of silica—approx. inch) to provide the desired compound as a yellow colored solid (0.3 g, 53% yield).

1. customAfter completion of reaction (monitored by TLC)
2. temperaturethe reaction mixture was cooled to RT
3. customquenched with 1N hydrochloric acid (100 mL)
4. extractionextracted with EtOAc (3×100 mL)
5. concentrationthe organic layer concentrated under reduced pressure
6. customThe crude product was purified by column chromatography (70% EtOAc:hexane in silica 100-200 mesh, diameter of column—5 cm, height of silica—approx. inch)

ORD record

ord-68b51c3592ba4b908593bd9a115df16f

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193728B2