Triethylamine → 2-Chloro-4-(2-(trimethylsilyl)ethynyl)pyridine

2-Chloro-4-iodo-pyridine (10 g, 42 mmol), palladium bis(triphenylphosphine)dichloride (2.93 g, 4.18 mmol) and triphenylphosphine (1.09 g, 4.17 mmol) are dissolved in de-gased dry THF (10 mL) and triethylamine (42 mL, 301 mmol). The resulting mixture is stirred for 1 hr at room temperature. Then Copper (I) iodide (2.3 g, 12 mmol) and ethynyl-trimethyl-silane (7.1 mL, 50 mmol) are added. The reaction mixture is stirred for 12 hrs at room temperature. The solvents are removed and the residue is diluted with water (100 mL). The mixture is extracted with EtOAc (3×250 mL) and the organic layers are combined, washed with brine, dried over anhydrous Na2SO4 and concentrated to give the crude product. Purification by silica flash column chromatography using 0.5% EtOAc in hexanes affords 4.6 g of the desired product.

1. stirringThe reaction mixture is stirred for 12 hrs at room temperature
2. customThe solvents are removed
3. additionthe residue is diluted with water (100 mL)
4. extractionThe mixture is extracted with EtOAc (3×250 mL)
5. washwashed with brine
6. dry with materialdried over anhydrous Na2SO4
7. concentrationconcentrated
8. customto give the crude product
9. customPurification by silica flash column chromatography

ORD record

ord-25a34158e4a8433e920437f4cac7361a

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722709B2