Methyl iodide → 3-Iodo-1-methyl-1H-indazole-6-carbonitrile

To a suspension of 3-iodo-1H-indazole-6-carbonitrile (2.0 g, 7.43 mmol), t-BuOK (1.2 g, 10.4 mmol) in THF (50 mL), iodomethane (1.2 g, 10.4 mmol) in THF (5 mL) was added dropwise at 0° C. under ice-water bath. The resulting mixture was stirred overnight at room temperature. Two isomers, which are methylated at N-1 and N-2 position respectively, were formed. The excess solvent was removed under reduced pressure, the residue was dissolved in EtOAc (100 mL), washed with brine (2×10 mL), the combined organics were dried over Na2SO4. After removal of drying agent and concentration, the crude mixture (1.6 g) was used in the next step without further purification. MS: (M+H)+=411;

1. additionwas added dropwise at 0° C. under ice-water bath
2. customwere formed
3. customThe excess solvent was removed under reduced pressure
4. dissolutionthe residue was dissolved in EtOAc (100 mL)
5. washwashed with brine (2×10 mL)
6. dry with materialthe combined organics were dried over Na2SO4
7. customAfter removal
8. customof drying
9. concentrationagent and concentration
10. customthe crude mixture (1.6 g) was used in the next step without further purification

ORD record

ord-a3f8d71b88b8448eb8289c717a01a756

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08658646B2