HCID 178526495, compound → HCID 178507363, compound

Temperature

90 °C

A suspension of 3-iodo-5-nitro-1H-indazole (2.0 g, 6.92 mmol) in stabilized hydroiodic acid (57% wt aqueous solution, 21 mL) was heated at about 90° C. for about 2 hours. The reaction mixture became homogeneous as the reaction progressed. After cooling to ambient temperature, the dark purple mixture was diluted with EtOAc (500 mL) and washed successively with saturated aqueous sodium thiosulfate (200 mL), saturated aqueous NaHCO3 (200 mL) and brine (200 mL). The colorless organic layer was dried over anhydrous magnesium sulfate, and concentrated to dryness to give 3-iodo-1H-indazol-5-ylamine: 1H NMR (DMSO-d6, 400 MHz) 13.03 (s, 1H), 7.26 (d, 1H), 6.85 (m, 1H), 6.44 (d, 1H), 5.03 (s, 2H); LC/MS (30% to 95% acetonitrile/0.01M aqueous ammonium acetate over 4.5 min at 0.8 mL/min; λ=190-700 nm; Genesis C18, 3 μm, 30×4.6 mm column; Electrospray ionization method observing both +ve and −ve ions) Rt 1.25 min.; m/z: 260 (M+H)+.

1. temperatureAfter cooling to ambient temperature
2. washwashed successively with saturated aqueous sodium thiosulfate (200 mL), saturated aqueous NaHCO3 (200 mL) and brine (200 mL)
3. dry with materialThe colorless organic layer was dried over anhydrous magnesium sulfate
4. concentrationconcentrated to dryness

ORD record

ord-f194e4dfc8094f1799b8f7bd9cd66c36

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08008481B2