Water → 3-styryl-1-[2-(trimethyl-silanyl)-ethoxymethyl]-1H-indazol-6-ylamine

Temperature

50 °C

6-Nitro-3-styryl-1-[2-(trimethyl-silanyl)-ethoxymethyl]-1H-indazole (8.1 g, 20.5 mmol) was dissolved in DMF (75 mL) at 23° C. under an atmosphere of argon. SnCl2 (12.9 g, 67.7 mmol) was added followed by water (1.7 mL, 92.2 mmol) and the resulting mixture was heated to 50° C. After 4 h, 3N NaOH (45 mL, 135 mmol) was added followed by EtOAc (100 mL). The resulting emulsion was filtered hot through Celite and the bed of Celite was washed with hot EtOAc (3×100 mL). The filtrate was concentrated under reduced pressure, the residue was dissolved in EtOAc, washed with brine, dried with Na2SO4, filtered and concentrated under reduced pressure to give a solid. The crude material was purified by silica gel chromatography (2:8→7:3 ethyl acetate:hexane), to give 3-styryl-1-[2-(trimethyl-silanyl)-ethoxymethyl]-1H-indazol-6-ylamine as a yellow solid (5.1 g, 68% yield). MS (FAB) [M+H]/z Calc'd 366, found 366.

1. filtrationThe resulting emulsion was filtered hot through Celite
2. washthe bed of Celite was washed with hot EtOAc (3×100 mL)
3. concentrationThe filtrate was concentrated under reduced pressure
4. dissolutionthe residue was dissolved in EtOAc
5. washwashed with brine
6. dry with materialdried with Na2SO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customto give a solid
10. customThe crude material was purified by silica gel chromatography (2:8→7:3 ethyl acetate:hexane)

ORD record

ord-5b2869d7d7194cf290992cf1806cdea4

Source dataset

uspto-grants-2003_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06531491B1