Benzenesulfonyl chloride → N-{2,6-Dimethyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}benzenesulfonamide

To a stirred solution of 2,6-dimethyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-amine (100 mg, 0.352 mmol) (Description 4) in THF (2 mL), cooled in an ice bath, was added LiHMDS (1M solution in THF) (0.774 mL, 0.774 mmol). The reaction mixture was stirred at RT for 45 min before the addition of benzenesulfonyl chloride (0.155 g, 0.879 mmol). The reaction mixture was then stirred at RT for a further 12 h. The reaction mixture was then diluted with water (15 mL) and the aqueous layer extracted with DCM (3×30 mL) and the combined organic extracts dried over a phase separating column and concentrated. MeOH (ca. 0.5 mL) was added to the residue which resulted in the precipitation of a solid. The solid was filtered, washed with MeOH (2 mL) and dried, to afford the title compound (88 mg). LCMS (A) m/z: 425 [M+1]+, Rt 1.40 min (basic).

1. extractionthe aqueous layer extracted with DCM (3×30 mL)
2. customthe combined organic extracts dried over a phase
3. customseparating column
4. concentrationconcentrated
5. additionMeOH (ca. 0.5 mL) was added to the residue which
6. customresulted in the precipitation of a solid
7. filtrationThe solid was filtered
8. washwashed with MeOH (2 mL)
9. customdried

ORD record

ord-3a9db9316d884e9bbe90c818e301f47b

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09029545B2