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

HRID 218452

反応式

HRID 218452 の反応式
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

参加物

7

反応物 3

HCID 218947395-Iodo-1H-indazoleHCID 178418416HCID 178418416、化合物HCID 178526064HCID 178526064、化合物

生成物 1

HCID 212506441H-Indazole-5-carboxaldehyde収率 59%

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-409fa49f0ea84d03acfb949dd7ff02f8
出典データセット
uspto-grants-2012_06
特許番号
US08198456B2

関連ノート

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