Hydrazine hydrate (1:1) → 6-fluoro-7-iodo-1H-pyrazolo[4,3-b]pyridin-3-amine

HRID 1522560Notes

Reaction equation

HRID 1522560 reaction equation
F[C:2]1[C:3]([C:10]#[N:11])=[N:4][CH:5]=[C:6]([F:9])[C:7]=1[I:8].O.[NH2:13][NH2:14]>C(O)CCC>[F:9][C:6]1[C:7]([I:8])=[C:2]2[NH:14][N:13]=[C:10]([NH2:11])[C:3]2=[N:4][CH:5]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 674695943,5-Difluoro-4-iodopicolinonitrile

Product 1

HCID 674704486-fluoro-7-iodo-1H-pyrazolo[4,3-b]pyridin-3-amineYield 28%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
105 °C

Procedure

3,5-Difluoro-4-iodopicolinonitrile (1.0 g) was combined with butan-1-ol (10 mL) and hydrazine hydrate (100%, 0.82 mL) was added. The reaction was heated at 105° C. and after 2 hours cooled to room temperature, filtered, the filter rinsed with water, and the filtrate was concentrated to give a residue. The residue was washed with water and filtered to give 6-fluoro-7-iodo-1H-pyrazolo[4,3-b]pyridin-3-amine (27) as a solid (290 mg, 28% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.14 (s, 1H) 5.59 (s, 2H). MS [M+H] found 279.0

Workup

  1. additionwas added
  2. temperaturecooled to room temperature
  3. filtrationfiltered
  4. washthe filter rinsed with water
  5. concentrationthe filtrate was concentrated
  6. customto give a residue
  7. washThe residue was washed with water
  8. filtrationfiltered

Sources & evidence

ORD record
ord-f3d02b57b93c4822aa53b16c8d933644
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

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