2-Methyl-3-butyn-2-ol → 2-methyl-4-(3-pyridinyl)-3-butyn-2-ol

Temperatur

0 °C

3-Bromopyridine (3.0 mL, 31 mmol), triethylamine (22 mL, 160 mmol), CuI (1.2 g, 6.2 mmol), and PdCl2(PPh3)2 (1.1 g, 1.5 mmol) were combined in DME (92 mL) and cooled to 0° C. 2-Methyl-3-butyne-2-ol (9.0 mL, 93 mmol) was then added and the reaction was allowed to slowly warm to ambient temperature. The mixture was then heated to 55-60° C. for 16 h. The mixture was filtered through Celite.™, and the pad was washed thoroughly with ethyl acetate. The combined filtrates were washed with brine (3.times.100 mL), dried over MgSO4, and filtered. The solution was concentrated in vacuo, and the residue was purified by column chromatography eluting with 90:10 hexane:ethyl acetate then ethyl acetate to afford 2-methyl-4-(3-pyridinyl-)-3-butyn-2-ol (2.0 g, 40% yield) as a brown oil 1H NMR (CDCl3, 300 MHz) Δ8.76 (br s, 1H), 8.52 (br s, 1H), 7.74-7.70 (m, 1H), 4.08 (br s, 1H), 1.63 (s, 3H). MS (EI ionization) 161 (M+).

1. temperatureto slowly warm to ambient temperature
2. temperatureThe mixture was then heated to 55-60° C. for 16 h
3. filtrationThe mixture was filtered through Celite
4. wash™, and the pad was washed thoroughly with ethyl acetate
5. washThe combined filtrates were washed with brine (3.times.100 mL)
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationThe solution was concentrated in vacuo
9. customthe residue was purified by column chromatography
10. washeluting with 90:10 hexane

ORD-Eintrag

ord-9568c80e19864185ac7bdaae5223877d

Quelldatensatz

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07365074B2