Hydrochloric Acid → 1-(pyridin-3-ylmethyl)-1H-indazol-4-amine

To a vial containing 3-iodo-4-nitro-1-(pyridin-3-ylmethyl)-1H-indazole (0.145 g, 0.381 mmol) was added THF (2.4 mL) and MeOH (1.2 mL). To this solution was added Zn dust (0.249 g, 3.81 mmol) followed by HCl (2.54 mL, 7.63 mmol, 3.0 M aqueous). The mixture was stirred for 1.0 hours. The mixture was filtered through GF/F paper and the collected solids were washed with CHCl3 (30 mL). A saturated aqueous KOAc solution was added to the filtrate until the pH was neutral and then a saturated aqueous Rochelle's Salt solution was added. The mixture was stirred vigorously, the layers were separated and the aqueous phase was extracted with CHCl3. The combined organic extracts were washed with brine and dried over Na2SO4, filtered and concentrated. The product was purified by column chromatography (1 to 10% MeOH/CH2Cl2) to afford the product as a thick oil (0.041 g, 47%).

1. filtrationThe mixture was filtered through GF/F paper
2. washthe collected solids were washed with CHCl3 (30 mL)
3. additionA saturated aqueous KOAc solution was added to the filtrate until the pH
4. additiona saturated aqueous Rochelle's Salt solution was added
5. stirringThe mixture was stirred vigorously
6. customthe layers were separated
7. extractionthe aqueous phase was extracted with CHCl3
8. washThe combined organic extracts were washed with brine
9. dry with materialdried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated
12. customThe product was purified by column chromatography (1 to 10% MeOH/CH2Cl2)

ORD record

ord-aa0ffd0957974fd3b04c6ba55d438019

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09174981B2