3,5-DIBROMO-4-CHLOROPYRIDINE

To 3, 5-dibromo-4-(1 /-/)-pyridone (0.25 g, 1.0 mmol) was added POCICompound (M-41) (10.0 g, 39.5 mmol) was suspended in acetonitrile (50 mL), DIPEA (15 mL, 87 mmol) wasadded at room temperature, phosphoryl chloride (7.4 mL, 79 mmol) was added under ice-cooling, and the mixture wasstirred with heating under reflux for 17 hr. The mixture was allowed to cool, and the reaction mixture was added dropwiseto ice water, and neutralized with sodium carbonate (11.6 g, 138 mmol). Thereafter, the mixture was extracted with ethylacetate, and the organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solventwas evaporated under reduced pressure to give a chloro compound (yield 10.6 g, 99percent) as a brown solid. The chlorocompound (10.6 g, 39.1 mmol) was dissolved in THF (70 mL), sodium methoxide (28percent methanol solution, 14 mL, 59mmol) was added, and the mixture was stirred at 60°C for 30 min. The mixture was allowed to cool, water was addedto the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successivelywith water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reducedpressure to give compound (VII-46) (yield 9.21 g, 88percent) as a yellow solidIn a round-bottom flask, equipped with a stirrer, thermometer and reflux condenser, mix under nitrogen in the specified order: 120 mL of phosphoryl chloride and 38 g (150 mmol) of BCD-BTK-104-9. Stir the reaction mass at 70 °C for 3 hours, cool it to 40 °C, and pour on ice, while stirring vigorously. Filter the precipitate, wash with water, and dry under vacuum at 40 °C. Yield: 36.7 g (91percent).3, 5-dibromopyridin-4-ol (239) (1.00 g, 3.95 mmols) was combined with phosphoryl chloride (921.45 µl, 9.89 mmols) in a pressure stable vessel. The vessel was closed and the solution heated to 140 °C under stirring for 2.5 h. Afterwards the reation vessel was cooled down to rt and the reaction solution combined with ice cold water (75 mL). The aqueous layer was extracted with EtOAc (5 x 15 mL) and the combined organic layers were dried over anhydrous magnesium sulfate. The product was dried in vacuo. Purification of the crude was performed by silica gel column chromatography (1percent EtOAc/n‑pentane) to obtain the product (805 mg, 2.97 mmols,  75percent) as a white solid. R

Molecular Weight:271.34
XLogP3:2.9
Hydrogen Bond Acceptor Count:1
Exact Mass:270.82220
Monoisotopic Mass:268.82425
Topological Polar Surface Area:12.9
Heavy Atom Count:9
Complexity:91
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes