Methylhydrazine → 4-Iodo-1-methyl-1H-indazol-3-amine

Temperature

120 °C

To a 330 mL pressure vessel equipped with a magnetic stir bar was added 2-fluoro-6-iodobenzonitrile (4.5 g, 18.2 mmol), N,N-dimethylacetamide (45 mL), and methylhydrazine (1.2 mL 23.7 mmol). The vessel was flushed with N2 gas, sealed and heated at 87° C. overnight and at 120° C. for 5 h. The reaction mixture was cooled, diluted with EtOAc (300 mL, and washed with water. The aqueous layer was extracted and the combined EtOAc extracts were washed with water (3×150 mL), brine, dried (Na2SO4), filtered and concentrated to a brown solid. The solid was triturated with EtOAc/hexanes (1:1, 10 mL), filtered, washed with EtOAc/hexanes (1:1) and dried to give 4.04 g (81%) of I-216 as a beige solid. 1H NMR (400 MHz, DMSO-d6)

1. customTo a 330 mL pressure vessel equipped with a magnetic stir bar
2. customThe vessel was flushed with N2 gas
3. customsealed
4. temperatureThe reaction mixture was cooled
5. additiondiluted with EtOAc (300 mL
6. washwashed with water
7. extractionThe aqueous layer was extracted
8. washthe combined EtOAc extracts were washed with water (3×150 mL), brine
9. dry with materialdried (Na2SO4)
10. filtrationfiltered
11. concentrationconcentrated to a brown solid
12. customThe solid was triturated with EtOAc/hexanes (1:1, 10 mL)
13. filtrationfiltered
14. washwashed with EtOAc/hexanes (1:1)
15. customdried
16. customto give 4.04 g (81%) of I-216 as a beige solid

ORD record

ord-34d1c22ee50e431c9c16824736155b2b

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07598397B2