2-Bromopyridine → 3-(Pyridin-2-yloxy)propan-1-amine

3-Aminopropan-1-ol (0.28 ml, 3.64 mmol) was added to a mixture of NaH 60% dispersion in mineral oil (16 mg, 4.11 mmol) in dry THF (8 ml) at rt. The resulting mixture was heated at reflux for 35 mins and cooled to rt before 2-bromopyridine (0.50 g, 3.16 mmol) was added. The mixture was then refluxed for 2 h 20 mins and stirred at rt for another 17 h before more NaH (127 mg, 3.16 mmol) was added and the mixture heated at reflux for 3 h. The mixture was evaporated to dryness, water was added, and the mixture was acidified to pH5 with 1N HCl and washed with DCM. The aqueous phase was then basified to pH4 and extracted again with DCM. The organic extracts were combined and evaporated to give the title compound (0.206 g, 43%) as an oil. 1H NMR (500 MHz CDCl3): 8.17-8.12 (m, 1H), 7.58-7.53 (m, 1H), 6.67-6.63 (m, 1H), 6.72 (d, 1H), 4.39 (t, 2H), 2.88 (t, 2H), 1.93 (quintet, 2H). 13C NMR (125 MHz CDCl3): 164.1, 147.1, 138.7, 116.8, 111.3, 63.8, 39.5, 33.3.

1. temperatureThe resulting mixture was heated
2. temperatureat reflux for 35 mins
3. additionwas added
4. temperatureThe mixture was then refluxed for 2 h 20 mins
5. additionwas added
6. temperaturethe mixture heated
7. temperatureat reflux for 3 h
8. customThe mixture was evaporated to dryness, water
9. additionwas added
10. washwashed with DCM
11. extractionextracted again with DCM
12. customevaporated

ORD record

ord-c1fdc516bba94e69b21ee9b19994446b

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07723333B2