2-Bromopyridine → HCID 15053368, compound

Temperature

65 °C

The maleate salt of 1-(1-phenylethyl)-3-azetidinol (65 g, 0.22 mole) was partitioned between toluene and dilute sodium hydroxide and was extracted once with toluene. The organic layer was dried (sodium sulfate) and concentrated. The residue was dissolved in 125 ml of dimethylformamide and added dropwise to a stirred suspension of 9.6 g (0.24 mole) of sodium hydride (washed three times with isooctane) in 400 ml of dimethylformamide at 25°-35° C. The solution was heated to 65° C. and 35 g (0.22 mole) of 2-bromopyridine was added dropwise while heating to 75° C. The solution was stirred and heated at 90° C. for 1 hr followed by heating at 120° C. for 2.75 hr. The mixture was stirred at room temperature overnight and concentrated. The residue was partitioned between water and isopropyl ether. The organic layer was washed twice with water, dried (sodium sulfate), filtered and concentrated. Crude yield was 30 g. The residue was distilled to give 8 g of product, bp 128°-134° C./0.01 mm.

1. extractionwas extracted once with toluene
2. dry with materialThe organic layer was dried (sodium sulfate)
3. concentrationconcentrated
4. dissolutionThe residue was dissolved in 125 ml of dimethylformamide
5. temperaturewhile heating to 75° C
6. temperatureheated at 90° C. for 1 hr
7. temperatureby heating at 120° C. for 2.75 hr
8. stirringThe mixture was stirred at room temperature overnight
9. concentrationconcentrated
10. customThe residue was partitioned between water and isopropyl ether
11. washThe organic layer was washed twice with water
12. dry with materialdried (sodium sulfate)
13. filtrationfiltered
14. concentrationconcentrated
15. distillationThe residue was distilled

ORD record

ord-b9c6e95c792c42819ff162eee87e0f75

Source dataset

uspto-grants-1993_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05183902