Hexane → HCID 9877431, compound

Temperature

55 °C

2-Bromo-1,3-thiazole (2.0 g, 12 mmol) and CuI (456 mg, 2.4 mmol) were combined in DME (30 mL) and argon gas was bubbled through the suspension for several minutes to deoxygenate the mixture. Triethylamine (8.6 mL, 60 mmol) and PdCl2(PPh3)2 (842 mg, 1.2 mmol) were added and methyl propargyl ether (1.00 g, 14.4 mmol) was added dropwise. The reaction was stirred at 55° C. under a condenser. After stirring at 55° C. for 16 h, 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, 99:1, 97:3, then 96:4 hexane:ethyl acetate to afford methyl 3-(1,3-thiazol-2-yl)-2-propynyl ether (250 mg, 13% yield) as a yellow oil. 1H NMR (CDCl3, 300 MHz) δ 7.78 (d, J=3.0 Hz, 1H), 7.37 (d, J=3.0 Hz, 1H), 4.37 (s, 2H), 3.47 (s, 3H). MS (ESI) 154.1 (M++H).

1. customargon gas was bubbled through the suspension for several minutes
2. customto deoxygenate the mixture
3. stirringAfter stirring at 55° C. for 16 h
4. filtrationThe mixture was filtered through Celite™
5. washthe filter pad was washed thoroughly with ethyl acetate
6. concentrationThe combined filtrates were concentrated in vacuo
7. dissolutionthe residue was dissolved in ethyl acetate (300 mL)
8. washwashed with water (300 mL), brine (300 mL)
9. dry with materialdried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated in vacuo
12. customThe residue was purified by column chromatography
13. washeluting with hexane, 99:1, 97:3

ORD record

ord-541f82906eb546b082ad1c96a583e627

Source dataset

uspto-grants-2004_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06774138B2