5-Iodo-1H-indazole → 1H-Indazole-5-carboxaldehyde

HRID 218452

반응식

HRID 218452 반응식
I[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.[CH:11](O[Na])=[O:12].[C]=O>CN(C=O)C.[Cl-].[Na+].O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH:7]1[C:8]2[C:4](=[CH:3][C:2]([CH:11]=[O:12])=[CH:10][CH:9]=2)[CH:5]=[N:6]1

참가 물질

7

반응물 3

HCID 218947395-Iodo-1H-indazoleHCID 178418416HCID 178418416, 화합물HCID 178526064HCID 178526064, 화합물

생성물 1

HCID 212506441H-Indazole-5-carboxaldehyde수율 59%

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

실험 절차

A mixture of 5-iodoindazole (10 g, 41 mmol), HCOONa (5.57 g, 82 mmol) and PdCl2(PPh3)2 (1.44 g, 2.05 mmol) in DMF (60 mL) was put under vacuum and charged with carbon monoxide (CO). This process was repeated three times, after which the mixture was kept at 110° C. for 6 hr. After cooling to room temperature (rt), the reaction mixture was diluted with brine and extracted with EtOAc. The organic phases were combined, washed with brine, dried, and concentrated. The crude product was purified by column chromatography to afford 1H-indazole-5-carboxaldehyde (3.52 g, 59%) as a white solid.

후처리

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography

출처 및 근거

ORD 기록
ord-409fa49f0ea84d03acfb949dd7ff02f8
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198456B2

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