5-iodo-N-methoxy-N-methyl-1H-indazole-3-carboxamide → 5-Iodo-1H-indazole-3-carbaldehyde

HRID 218461ノート

反応式

HRID 218461 の反応式
[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[C:11](N(OC)C)=[O:12].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[CH:11]=[O:12]

参加物

4

反応物 2

HCID 205807385-iodo-N-methoxy-N-methyl-1H-indazole-3-carboxamideHCID 21226445Aluminium lithium hydride

生成物 1

HCID 1785200355-Iodo-1H-indazole-3-carbaldehyde収率 58.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 5-iodo-N-methoxy-N-methyl-1H-indazole-3-carboxamide (500 mg, 1.51 mmol), from Synthetic Preparation 6, in THF (10 mL) at 0° C. was added lithium aluminum hydride (61 mg, 1.66 mmol). After 30 min, the reaction was quenched by the slow addition of EtOAc followed by 0.4N NaHSO4, and extracted. The organic layer was washed with brine, dried, and concentrated. The crude product was purified by flash chromatography to give 5-iodo-1H-indazole-3-carboxaldehyde (240 mg, 58.2%).

後処理

  1. customthe reaction was quenched by the slow addition of EtOAc
  2. extractionextracted
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography

出典と根拠

ORDレコード
ord-5fc2b1c1673d47bf8439ad9dccac66dc
出典データセット
uspto-grants-2012_06
特許番号
US08198456B2

反応ノート

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