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 1949552ノート

反応式

HRID 1949552 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-88ebdf894b164f79b40aa1247d40d498
出典データセット
uspto-grants-2013_03
特許番号
US08399681B2

反応ノート

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