Potassium Acetate → 3-Methyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)thietane 1,1-dioxide

Temperatur

90 °C

Step D To pinacol diboronate (250 mg, 0.986 mmol), potassium acetate (242 mg, 2.466 mmol) and PdCl2(dppf)-CH2Cl2 adduct (67 mg, 0.082 mmol) in a thick-walled tube was added a solution of 3-(4-bromophenyl)-3-methylthietane 1,1-dioxide (226 mg, from Step C) in DMF (5 ml). The tube was flushed with N2, then capped and heated to 90° C. for 4 hours. Then the reaction was cooled to RT and diluted with EtOAc (30 ml) and water (20 ml). The aqueous layer was separated and extracted with EtOAc (25 ml). The combined organic layers were washed with water (50 ml), dried (Na2SO4), filtered and concentrated. The resulting crude material was purified by Isco™ system, 40 g gold cartridge, 40 ml flow rate, gradient—0/100 (1 min) to 50/50 (19 min) to 50/50 (21 min—total run time) of EtOAc/hexanes. The fractions containing the product were combined and concentrated to provide 3-methyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)thietane 1,1-dioxide as a white solid.

1. customThe tube was flushed with N2
2. customcapped
3. temperatureThen the reaction was cooled to RT
4. additiondiluted with EtOAc (30 ml) and water (20 ml)
5. customThe aqueous layer was separated
6. extractionextracted with EtOAc (25 ml)
7. washThe combined organic layers were washed with water (50 ml)
8. dry with materialdried (Na2SO4)
9. filtrationfiltered
10. concentrationconcentrated
11. customThe resulting crude material was purified by Isco™ system, 40 g gold cartridge, 40 ml flow rate, gradient—0/100 (1 min) to 50/50 (19 min) to 50/50 (21 min—total run time) of EtOAc/hexanes
12. additionThe fractions containing the product
13. concentrationconcentrated

ORD-Eintrag

ord-a768ca25f8bc4002b5a65b7cd1c0aca4

Quelldatensatz

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09290517B2