Water → 6-formyl-1H-indazole-3-carbonitrile

HRID 2383662Notes

Reaction equation

HRID 2383662 reaction equation
I[C:2]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]=[O:12])=[CH:8][CH:9]=2)[NH:4][N:3]=1.[Cu](C#N)[C:14]#[N:15].O>CN(C=O)C>[CH:11]([C:7]1[CH:6]=[C:5]2[C:10]([C:2]([C:14]#[N:15])=[N:3][NH:4]2)=[CH:9][CH:8]=1)=[O:12]

Participants

5

Reactant 3

HCID 962WaterHCID 178418260HCID 178418260, compoundHCID 178519327HCID 178519327, compound

Product 1

HCID 768462446-formyl-1H-indazole-3-carbonitrileYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-iodo-1H-indazole-6-carbaldehyde (3 g, 10.8 mmol) in DMF (25 mL) was added Copper cyanide (1.9 g, 21 mmol). The solution was heated by microwave irradiation at 185° C. for 10 min Water (100 mL) was added and a white precipitate was collected. The precipitate was dissolved in EtOAc (250 mL), washed with water (2×25 mL), dried over MgSO4 and concentrated to give the title compound as a white solid (1.1 g, 73%). 1H NMR (400 MHz, DMSO-d6) δ 14.92 (bs, 1H), 10.17 (s, 1H), 8.39 (s, 1H), 8.06 (d, J=8.3 Hz, 1H), 7.83 (d, J=8.5 Hz, 1H).

Workup

  1. additionwas added
  2. customa white precipitate was collected
  3. dissolutionThe precipitate was dissolved in EtOAc (250 mL)
  4. washwashed with water (2×25 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2da9c1b356e9484e97be23f90cd297c4
Source dataset
uspto-grants-2012_09
Patent number
US08263596B2

Reaction notes

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