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

HRID 227746Notes

Reaction equation

HRID 227746 reaction equation
F[C:2]1[N:9]=[CH:8][CH:7]=[C:6]([I:10])[C:3]=1[CH:4]=O.[NH2:11][NH2:12]>C1COCC1>[I:10][C:6]1[CH:7]=[CH:8][N:9]=[C:2]2[NH:11][N:12]=[CH:4][C:3]=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

To 2-fluoro-4-iodonicotinaldehyde (11.33 g, 45.1 mmol) in THF (200 mL) was added hydrazine (5.67ml, 181 mmol) dropwise. The resulting mixture was stirred at RT under a nitrogen atmosphere for 5 h. The reaction was concentrated, diluted with 10:1 acetone/MeOH and filtered through a pad of silica gel. Removed most of the solvent in vacuo, then diluted with some hexanes and filtered resulting solid. Dried to yield 4-iodo-1H-pyrazolo[3,4-b]pyridine as an off-white solid. MS m/z=246 [M+1]+. Calc'd for C6H4IN3: 245.02.

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with 10:1 acetone/MeOH
  3. filtrationfiltered through a pad of silica gel
  4. customRemoved most of the solvent in vacuo
  5. additiondiluted with some hexanes
  6. filtrationfiltered
  7. customresulting solid
  8. customDried

Sources & evidence

ORD record
ord-1eeb2bbef63445069296a73b75afc024
Source dataset
uspto-grants-2009_07
Patent number
US07560551B2

Reaction notes

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