Sodium Carbonate → HCID 57598244, Verbindung

Temperatur

100 °C

To a solution of (5-bromo-1,3,4-thiadiazol-2-yl)methanol (1.2 g, 6.15 mmol) in toluene (40 ml) and ethanol (40 ml) was added 4-fluorophenyl boronic acid (1.03 g, 7.38 mmol) and 2 M aqueous Na2CO3. The reaction mixture was degassed with argon, Pd(PPh3)4 (0.354 g, 0.355 mmol) was added, the reaction mixture was degassed again with argon for 10 min, and then heated to 100° C. for 2 h. The reaction mixture was evaporated under vacuum to remove ethanol, the reaction mixture was diluted with water (50 mL), and extracted with ethyl acetate (200 mL). The organic extracts were dried over sodium sulphate, filtered and evaporated under reduced pressure to obtain crude product. The crude product was purified by Biotage Isolera® One column (using 30% ethyl acetate and hexane) to give (5-(4-fluorophenyl)-1,3,4-thiadiazol-2-yl)methanol as a pale yellow solid (0.85 g, 65% yield); LC-MS m/z calcd for [M+H]+ 211.03. found 211.1

1. additionwas added
2. customthe reaction mixture was degassed again with argon for 10 min
3. customThe reaction mixture was evaporated under vacuum
4. customto remove ethanol
5. additionthe reaction mixture was diluted with water (50 mL)
6. extractionextracted with ethyl acetate (200 mL)
7. dry with materialThe organic extracts were dried over sodium sulphate
8. filtrationfiltered
9. customevaporated under reduced pressure
10. customto obtain crude product
11. customThe crude product was purified by Biotage Isolera® One column (using 30% ethyl acetate and hexane)

ORD-Eintrag

ord-b6077b0dca584e63b901f539d10d6337

Quelldatensatz

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09199975B2