2-(Tributylstannyl)pyridine → 2-(2-Pyridinyl)quinoline

Temperature

110 °C

A solution of 2-bromoquinoline (1.00 g, 4.81 mmol) [Aldrich, cat. #716278] in N,N-dimethylformamide (10.0 mL) (degassed with nitrogen) was treated with 2-(tributylstannyl)pyridine (1.83 mL, 4.81 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.337 g, 0.481 mmol). The reaction mixture was degassed with nitrogen for 5 min and heated at 110° C. for 17 h. The reaction mixture was then diluted with water (50 mL) and ether (50 mL) and filtered over Celite. The solids were washed with additional ether (150 mL). The filtrate was washed with water (150 mL) and brine, dried over sodium sulfate, filtered, and concentrated to give a crude residue. Purification by flash column chromatography (100% hexanes to 70% ethyl acetate/hexanes, the ethyl acetate containing 5% methanol) gave the desired product (0.771 g, 78%). LCMS calculated for C14H11N2 (M+H)+: m/z=207.1. found: 207.1.

1. customThe reaction mixture was degassed with nitrogen for 5 min
2. additionThe reaction mixture was then diluted with water (50 mL) and ether (50 mL)
3. filtrationfiltered over Celite
4. washThe solids were washed with additional ether (150 mL)
5. washThe filtrate was washed with water (150 mL) and brine
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customto give a crude residue
10. customPurification by flash column chromatography (100% hexanes to 70% ethyl acetate/hexanes

ORD record

ord-2f1faf5af9ca4d319a3f2a42a272de81

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09227985B2