1-(2,4-Bis-trifluoromethyl-benzyl)-3-iodo-1H-indazole-5-carbaldehyde → 1-[2,4-bis(trifluoromethyl)benzyl]-3-cyano-1H-indazol-5-carbaldehyde

HRID 1949552Notes

Reaction equation

HRID 1949552 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:4]=1[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([CH:15]=[O:16])=[CH:12][CH:13]=2)[C:8](I)=[N:7]1.[Cu][C:29]#[N:30]>CN(C)C=O>[F:1][C:2]([F:27])([F:26])[C:3]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:4]=1[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([CH:15]=[O:16])=[CH:12][CH:13]=2)[C:8]([C:29]#[N:30])=[N:7]1

Participants

4

Reactant 2

HCID 866545851-(2,4-Bis-trifluoromethyl-benzyl)-3-iodo-1H-indazole-5-carbaldehydeHCID 178418546HCID 178418546, compound

Product 1

HCID 866597001-[2,4-bis(trifluoromethyl)benzyl]-3-cyano-1H-indazol-5-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 5 mL microwave reaction vessel was charged with 1-(2,4-Bis-trifluoromethyl-benzyl)-3-iodo-1H-indazole-5-carbaldehyde (300 mg, 0.6 mmol), copper (I) cyanide (135 mg, 1.5 mmol), and N,N-dimethylformamide (4 mL). The vessel was sealed and subjected to microwave irradiation at 185° C. for 15 min. The reaction mixture was partitioned between EtOAc and water. The organic layers were washed with brine, dried over Na2SO4, and evaporated. The crude residue was purified by flash column chromatography on silica gel, eluting with EtOAc/hexanes (1:4 v/v), to afford the title compound as a white solid.

Workup

  1. customThe vessel was sealed
  2. customirradiation at 185° C. for 15 min
  3. customThe reaction mixture was partitioned between EtOAc and water
  4. washThe organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe crude residue was purified by flash column chromatography on silica gel
  8. washeluting with EtOAc/hexanes (1:4 v/v)

Sources & evidence

ORD record
ord-88ebdf894b164f79b40aa1247d40d498
Source dataset
uspto-grants-2013_03
Patent number
US08399681B2

Reaction notes

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