Hydrazine → 4-Iodo-1H-pyrazolo[3,4-b]pyridine

HRID 2115867Notes

Reaction equation

HRID 2115867 reaction equation
[NH2:1][NH2:2].F[C:4]1[C:9]([CH:10]=O)=[C:8]([I:12])[CH:7]=[CH:6][N:5]=1>O1CCCC1>[I:12][C:8]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:1][N:2]=[CH:10][C:9]=12

Participants

4

Reactant 2

HCID 9321HydrazineHCID 99923282-Fluoro-4-iodopyridine-3-carbaldehyde

Product 1

HCID 576428014-Iodo-1H-pyrazolo[3,4-b]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1M solution of hydrazine in tetrahydrofuran (150 mL) was added slowly to 2-fluoro-4-iodopyridine-3-carboxaldehyde (10 g, 39.84 mmol) to give a clear solution. The reaction mixture was stirred at RT for 16 h. The mixture was concentrated in vacuo and the remaining solid was triturated with DCM to give the title compound as a pale yellow solid (8 g). The DCM filtrate was also washed with saturated sodium bicarbonate and brine. The organic layer was dried over sodium sulfate and concentrated under vacuum. The crude material was purified by trituration with DCM to give additional 4-iodo-1H-pyrazolo[3,4-b]pyridine as a yellow solid. MS (ESI, pos. ion) m/z: 245.9 (M+1).

Workup

  1. customto give a clear solution
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe remaining solid was triturated with DCM

Sources & evidence

ORD record
ord-213bdbb837634fbc8828e0b3bcb9cca5
Source dataset
uspto-grants-2008_10
Patent number
US07435823B2

Reaction notes

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