Uses

2,6-Dibromo-3-fluoropyridine is a useful reagent for making GLP-1 receptor agonists.

Synthesis

1133434-13-5

41404-59-5

General procedure for the synthesis of 2,6-dibromo-3-fluoropyridine (37) from the compound (CAS: 1133434-13-5): In a 1L single necked round bottomed flask fitted with a ventilated reflux condenser, raw material 36 (4.00 g, 11.4 mmol) was added so that it was uniformly distributed at the bottom of the flask. The flask was placed in a room temperature oil bath and the temperature of the oil bath was raised to 80°C within 20 minutes and then gradually raised to 130°C within 30 minutes and maintained at this temperature until the feedstock was completely decomposed (solid converted to a viscous substance and gas release stopped). When the reaction was complete, the reaction mixture was cooled to room temperature. The reaction residue was extracted with ether (3 x 75 mL) and the ether extracts were combined. The organic phase was washed with saturated aqueous sodium bicarbonate (200 mL) and subsequently dried over anhydrous sodium sulfate. The desiccant was removed by filtration and the filtrate was concentrated under reduced pressure at room temperature to afford the target product 37 in 100% yield (3.00 g) as a yellow solid with a melting point of 47-48 °C.1H NMR (300 MHz, CDCl3) δ 7.44 (dd, 1H, J=3.3,8.4 Hz), 7.31 (m, 1H).

References

[1] Patent: US2009/82330, 2009, A1. Location in patent: Page/Page column 37

Raw materials

Preparation Products