2-(2-(tert-butyl)phenoxy)pyridin-

Synthesis

Synthesis of 1b 2-(2-(tert-butyl)phenoxy)pyridin-3-amine: 1a 2-(2-tert-butyl-phenoxy)-3-nitropyridine (7.2 g, 26.5 mmol) was dissolved in a solvent mixture of methanol and ethyl acetate (160 mL, 1:1 v/v). 10% palladium carbon catalyst (360 mg, 0.33 mmol) was added and the reaction mixture was stirred overnight under hydrogen atmosphere. Upon completion of the reaction, the reaction mixture was filtered through a Celite pad to remove the catalyst and the filtrate was subsequently concentrated to afford 7.2 g (100% yield) of the target product 1b as a white powder. Mass spectral analysis: [M + H]+ = 243.

References

[1] Patent: WO2005/70920, 2005, A1. Location in patent: Page/Page column 64-65
[2] Patent: US2006/173002, 2006, A1. Location in patent: Page/Page column 40
[3] Patent: US2006/293522, 2006, A1. Location in patent: Page/Page column 19
[4] Patent: US2007/4677, 2007, A1. Location in patent: Page/Page column 23-24
[5] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 14, p. 4206 - 4209