4-(4-Aminophenoxy)-N-methylpicolinamide

Light-Brown Solid

Sorafenib intermediate

To a solution of 4-aminophenol (1 g, 9.2 mmol) in DMF (20 mL) was added 1M potassium ier/-butoxide in THF (9.7 mL, 9.7 mmol) at room temperature. After 2h, (4-chloro(2-pyridyl))-N- methyl carboxamide (1.6 g, 9.2 mmol) and potassium carbonate (0.64 g, 4.6 mmol) were added, and then the reaction mixture was heated to 80 °C for 6h. After cooling, the reaction mixture was extracted with ethyl acetate (50 mL). The organic layer was washed with brine (20 mL) and dried over magnesium sulfate. The solvent was removed in vacuo. The residue was purified by column chromatography to afford 4-(4-Aminophenoxy)-N-methylpicolinamide (2.2 g, 80 %) as a light-brown solid.

[1] Patent: WO2005/82853, 2005, A1. Location in patent: Page/Page column 209
[2] Patent: CN108409648, 2018, A. Location in patent: Paragraph 0043; 0044
[3] Patent: CN105085388, 2018, B. Location in patent: Paragraph 0028; 0033; 0036; 0039; 0042; 0045; 0048
[4] Patent: CN107915676, 2018, A. Location in patent: Paragraph 0012-0014