Potassium Carbonate → HCID 89739148, compound

Temperature

70 °C

To a solution of 6-bromo-5-methyl-4H-pyrrolo[2,3-d]thiazole (2.5 g, 11.52 mmol) in anhydrous N,N-dimethylformamide (20 mL) was added 1-methoxypropan-2-yl methanesulfonate (3.87 g, 23.03 mmol), and potassium carbonate (3.18 g, 23.03 mmol) followed. The resulting reaction mixture was heated to 70° C. and allowed to stir over night at 70° C. The reaction mixture was washed with water and brine, extracted with acetic ester (30 mL×3). The combined organic phase was dried by anhydrous sodium sulphate, and then filtered. The filtrate was concentrated and purified by column chromatograph on silica gel eluted with (petrol ether/acetic ester 30:1→20:1→10:1) to the title compound (2.0 g, 60%) as orange oil. LCMS (M+H+) m/z: calc'd. 287.99. found 290.9.

1. customThe resulting reaction mixture
2. washThe reaction mixture was washed with water and brine
3. extractionextracted with acetic ester (30 mL×3)
4. dry with materialThe combined organic phase was dried by anhydrous sodium sulphate
5. filtrationfiltered
6. concentrationThe filtrate was concentrated
7. custompurified by column chromatograph on silica gel
8. washeluted with (petrol ether/acetic ester 30:1→20:1→10:1) to the title compound (2.0 g, 60%) as orange oil

ORD record

ord-74457589a9314d7da089467cb7847e3e

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09371331B2