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

HRID 1522545Notes

Reaction equation

HRID 1522545 reaction equation
F[C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[CH:6][C:7]=1[I:8].O.[NH2:12][NH2:13]>C(O)CCC>[I:8][C:7]1[CH:6]=[CH:5][N:4]=[C:3]2[C:9]([NH2:10])=[N:12][NH:13][C:2]=12

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 210758673-Fluoro-4-iodopyridine-2-carbonitrile

Product 1

HCID 674704857-iodo-1H-pyrazolo[4,3-b]pyridin-3-amine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
105 °C

Procedure

3-Fluoro-4-iodopicolinonitrile (25.6 g) was dissolved in n-butan-1-ol (250 mL) then hydrazine hydrate (100%, 23.3 mL) was added. The reaction was heated at 105° C. for 2 hours. The reaction mixture was cooled to room temperature, filtered, rinsed with water, and dried for 30 minutes under vacuum to give 7-iodo-1H-pyrazolo[4,3-b]pyridine-3-amine (25 g) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 5.35-5.55 (2H, m) 7.73-7.74 (1H, m) 7.939-7.94 (1H, m). MS [M+H] found 261.0.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. washrinsed with water
  4. customdried for 30 minutes under vacuum

Sources & evidence

ORD record
ord-6590580459594155aa36dac95d8557be
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

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