Pyridine → 2-azetidin-1-yl-5-bromopyridine

Temperature

170 °C

A mixture of 5-bromo-2-chloropyridine (Sigma-Aldrich, Buchs, Switzerland, 196 mg, 1.018 mmol), azetidine (Sigma-Aldrich, Buchs, Switzerland, 0.213 ml, 3.06 mmol) and pyridine (0.124 ml, 1.528 mmol) in DMA (2.5 ml) was heated under microwave irradiation at 150° C. for 10 min and 170° C. for 10 min. The reaction was not completed. Again azetidine (0.106 ml) was added and the RM was heated under microwave irradiation at 170° C. for 1 h. Then the RM was quenched with saturated aqueous NaHCO3 (50 ml) and extracted with EtOAc (2×). The combined organic layers were washed with brine (2×), dried over Na2SO4, filtered and evaporated to dryness to give the title compound as an off-white solid. (HPLC: tR 1.97 min (Method A); M+H=213, 215 (Br-pattern) MS-ES. 1H-NMR (d6-DMSO, 400 MHz) 8.12 (s, 1H), 7.70-7.60 (m, 1H), 6.37-6.29 (m, 1H), 3.96-3.86 (m, 4H), 2.34-2.24 (m, 2H))

1. temperaturethe RM was heated under microwave irradiation at 170° C. for 1 h
2. customThen the RM was quenched with saturated aqueous NaHCO3 (50 ml)
3. extractionextracted with EtOAc (2×)
4. washThe combined organic layers were washed with brine (2×)
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. customevaporated to dryness

ORD record

ord-25c6d8240e6342a8aa2c588ef496af37

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476294B2