2-Bromo-4-(tert-butyl)pyridine

A solution of 2- (dimethylamino) ethanol (4.79 ml, 47.8 mmol) in heptane (200 ml) was stirred in an ice bath under nitrogen. A solution of butyllithium in hexane (38.2 ml, 96 mmol) was slowly added via syringe and stirred at low temperature for 30 min. 4- (tert-Butyl) pyridine (7.0 ml, 47.8 mmol) was slowly added via syringe and the mixture was stirred at low temperature for 1 hour to give an orange solution. The solution was cooled in an iPrOH / CO2 bath and a cooled solution (ice bath) of perbromomethane (19.02 g, 57.3 mmol) dissolved in heptane (200 ml) was slowly added via cannula. The brown heterogeneous reaction mixture was stirred at low temperature for 1 hour and then allowed to warm to room temperature overnight. The mixture was again cooled in an ice bath and carefully quenched with water. The mixture was extracted twice with ether and the combined organics were washed with brine, dried, vacuum reduced and coated onto celite. The result was then eluted on a 300 g silica column using 10-20percent EtOAc / heptane. The brown fraction with Rf ~ 0.3 (10percent EtOAc / heptane) was collected to give 2.90 g of a brown oil (28percent) containing 2-bromo-4- (tert- butyl) pyridine.Step 2Compound L4-2 (3 g, 17.6 mmol) and trimethylsilyl bromide (7 ml, 53.05 mmol) were placed in a reaction flask, and 50 ml of propionitrile was then added to the reaction flask to obtain a mixture. The mixture was heated under reflux for reaction for 24 hours, and was allowed to cool to 20° C., followed by further addition of trimethylsilyl bromide (7 ml, 53.05 mmol) to the reaction flask. Next, the contents in the reaction flask were further heated under reflux for another 24 hours, and then the temperature was slowly reduced to 20° C. Thereafter, the reaction flask was vacuum pumped to remove the solvents from the contents in the reaction flask, a sodium carbonate aqueous solution was added to the reaction flask for neutralization, and the contents in the reaction flask were extracted using ethyl acetate to collect a first organic layer. The first organic layer was dehydrated using sodium sulfate (NaTo an oven-dried flask were added 2, 2?-(oxybis(3, 1-phenylene))bis(4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolane) (1 eq),

Molecular Weight:214.10
XLogP3:3.5
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:213.01531
Monoisotopic Mass:213.01531
Topological Polar Surface Area:12.9
Heavy Atom Count:11
Complexity:128
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes