Cesium carbonate → HCID 84714635, compound

4-bromothiophenol (1.15 g, 6.08 mmol), oxetan-3-yl 4-methylbenzenesulfonate (1.66 g, 7.3 mmol), and cesium carbonate (3.96 g, 12.16 mmol) were suspended in DMSO (6 ml). The reaction mixture was stirred for 2 days at rt, then diluted with water and EtOAc. The aqueous phase was extracted with EtOAc (×2); and the combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The resulting residue was purified by column chromatography on a Biotage™ 50 g column by eluting with 5% to 75% EtOAc:Hexane. The major peak was isolated, concentrated and dissolved in MeOH (10 mL), THF (10 mL) and water (5 mL). Oxone (4.05 g, 6.59 mmol) was added and the reaction was stirred overnight at rt, and then diluted with water and EtOAc. The EtOAc phase was washed with water, Na2S2O3, and brine, and then dried over Na2SO4, filtered and concentrated to provide the desired product. 1H NMR δ 7.80-7.75 (m, 4H), 4.96 (t, 2H), 4.82 (t, 2H), 4.46 (pentet, 1H).

1. extractionThe aqueous phase was extracted with EtOAc (×2)
2. washand the combined extracts were washed with brine
3. dry with materialdried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated
6. customThe resulting residue was purified by column chromatography on a Biotage™ 50 g column
7. washby eluting with 5% to 75% EtOAc
8. customThe major peak was isolated
9. concentrationconcentrated
10. dissolutiondissolved in MeOH (10 mL)
11. stirringthe reaction was stirred overnight at rt
12. washThe EtOAc phase was washed with water, Na2S2O3, and brine
13. dry with materialdried over Na2SO4
14. filtrationfiltered
15. concentrationconcentrated

ORD record

ord-1a238083300e4523970065d9bb1d7411

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09382243B2