Water → HCID 58654355, compound

Temperature

67.5 °C

A catalytic amount of dichloropalladium(II)bis(triphenylphosphine) (189 mg, 268 μmol) was added to a solution of 5-chloro-3-imidazol-1-yl-[1,2,4]thiadiazole (500 mg, 2.68 mmol) and tributyl-(1-ethoxy-vinyl)-stannane (904 μL, 2.68 mmol) in DMF (10 mL) under a nitrogen atmosphere at r.t. prior to heating at 65-70° C. for 21 h. The reaction was then cooled to r.t., H2O (70 mL) was added, filtered through celite, and washed with EtOAc (200 mL). The organic layer was separated, dried over Na2SO4, filtered and concentrated to a yellow residue. The yellow residue was diluted with a 5:1 mixture of 5N HCl/THF (48 mL) and stirred at r.t. for a period of 2 hours prior to concentrating to a white residue. The crude product was diluted with EtOAc (100 mL), washed with 1M NaOH (75 mL), brine (75 mL), dried over Na2SO4, filtered and concentrated to a white solid. Purification was achieved using column chromatography (CH2Cl2 to 9:1 CH2Cl2/MeOH) to afford 398 mg (77%) of 1-(3-imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-ethanone as a white solid. [M+H]+ 195.35.

1. temperatureThe reaction was then cooled to r.t.
2. filtrationfiltered through celite
3. washwashed with EtOAc (200 mL)
4. customThe organic layer was separated
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated to a yellow residue
8. additionThe yellow residue was diluted with a 5:1 mixture of 5N HCl/THF (48 mL)
9. concentrationto concentrating to a white residue
10. additionThe crude product was diluted with EtOAc (100 mL)
11. washwashed with 1M NaOH (75 mL), brine (75 mL)
12. dry with materialdried over Na2SO4
13. filtrationfiltered
14. concentrationconcentrated to a white solid
15. customPurification

ORD record

ord-a463d9ccd4fe40ff8a3b0cdacb557688

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07825256B2