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

HRID 218461노트

반응식

HRID 218461 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 1785200355-Iodo-1H-indazole-3-carbaldehyde수율 58.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-5fc2b1c1673d47bf8439ad9dccac66dc
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198456B2

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