14884-01-6

Intermediate 6: Synthesis of 4-methoxy-1H-pyrazole 4-(Methoxy)-1-(phenylmethyl)-1H-pyrazole (Intermediate 5) (2.78 g, 15 mmol) was dissolved in methanol (60 mL). To this solution was added 1 M HCl (6.8 mL) and 20% Pd(OH)2 (2.78 g, 3.8 mmol). The reaction system was evacuated and subsequently rinsed with N2, evacuated again and rinsed with H2. The reaction mixture was stirred vigorously at room temperature for 36 hours. After completion of the reaction, the reaction mixture was filtered and the filtrate was concentrated under vacuum to afford the target compound 4-methoxy-1H-pyrazole (1.65 g, quantitative yield). The crude product obtained can be used directly in the subsequent reaction without further purification.

[1] Patent: WO2012/119978, 2012, A1. Location in patent: Page/Page column 51
[2] Patent: WO2016/124508, 2016, A1. Location in patent: Page/Page column 56
[3] Patent: US2012/202834, 2012, A1. Location in patent: Page/Page column 25
[4] Patent: WO2010/31589, 2010, A1. Location in patent: Page/Page column 45
[5] Patent: WO2015/95767, 2015, A1. Location in patent: Page/Page column 285; 286