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

HRID 1925373Notes

Reaction equation

HRID 1925373 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-d6d394a6014c4d8095b60088bd5b870e
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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