Triethylamine → 2-Bromo-4-(prop-1-ynyl)pyridine

To a solution of 2-bromo-4-iodopyridine (2 g, 7.04 mmo, copper(I) iodide (0.080 mL, 2.11 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.407 g, 0.35 mmol) in toluene (85 mL) was added 1-(trimethylsilyl)-1-propyne (1.054 mL, 7.04 mmol), triethylamine (3.24 mL, 23.25 mmol) and tetrabutylammonium fluoride (1 M in THF, 7.04 mL, 7.04 mmol) and the resulting mixture was stirred under an argon atmosphere at r.t. overnight. The mixture was concentrated and the resulting residue was partitioned between water (10 mL) and DCM (10 mL) and poured into a phase separator. The organic phase was collected, and the aqueous phase was extracted once with DCM (10 mL). The combined organics were concentrated and purified by flash chromatography using 0% to 30% EtOAc in heptane to give the title compound (1.195 g, 87% yield): 1H NMR (500 MHz, DMSO-d6) δ ppm 2.11 (s, 3 H), 7.42 (dd, 1 H), 7.65 (s, 1 H), 8.35 (dd, 1 H); MS (ES+) m/z 196 [M+H]+; MS (APCI+) m/z 196 [M+H]+.

1. concentrationThe mixture was concentrated
2. customthe resulting residue was partitioned between water (10 mL) and DCM (10 mL)
3. additionpoured into a phase separator
4. customThe organic phase was collected
5. extractionthe aqueous phase was extracted once with DCM (10 mL)
6. concentrationThe combined organics were concentrated
7. custompurified by flash chromatography

ORD record

ord-4d605109d1524bb9b67173b01a64c253

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08865911B2