Hexane → HCID 23500885, compound

2-Bromo-1,3-thiazole (3.1 g, 19 mmol) and CuI (290 mg, 1.5 mmol) were combined in DME (30 mL) and argon gas was bubbled through the suspension for several minutes to deoxygenate the mixture. Triethylamine (13 mL, 95 mmol) and PdCl2(PPh3)2 (530 mg, 0.76 mmol) were added and cyclohexylethyne (2.0 g, 19 mmol) was added dropwise. The reaction mixture was stirred at ambient temperature for 16 h at which time GC/MS analysis indicated that the reaction was complete. The mixture was filtered through Celite™, and the filter pad was washed thoroughly with ethyl acetate. The combined filtrates were concentrated in vacuo and the residue was dissolved in ethyl acetate (300 mL), washed with water (300 mL), brine (300 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography eluting with hexane then 99:1 hexane:ethyl acetate to afford 2-(cyclohexylethynyl)-1,3-thiazole (1.6 g, 44% yield) as a yellow oil. 1H NMR (CDCl3, 300 MHz) δ 7.76 (d, J=9.0 Hz, 1H), 7.28 (d, J=3.0 Hz, 1H), 2.68-2.59 (m, 1H), 1.91-1.28 (m, 10H). MS (ESI) 191.7 (M+).

1. customargon gas was bubbled through the suspension for several minutes
2. customto deoxygenate the mixture
3. filtrationThe mixture was filtered through Celite™
4. washthe filter pad was washed thoroughly with ethyl acetate
5. concentrationThe combined filtrates were concentrated in vacuo
6. dissolutionthe residue was dissolved in ethyl acetate (300 mL)
7. washwashed with water (300 mL), brine (300 mL)
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customThe residue was purified by column chromatography
12. washeluting with hexane

ORD record

ord-1566936678dc402abf27f743bbaa0461

Source dataset

uspto-grants-2004_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06774138B2