Methyl 5-bromo-1H-indazole-3-carboxylate → methyl 5-formyl-1H-indazole-3-carboxylate

HRID 218478

反応式

HRID 218478 の反応式
[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11](Br)[CH:12]=2)[NH:7][N:6]=1)=[O:4].[CH:15](O[Na])=[O:16]>CN(C=O)C.CCOC(C)=O.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>[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH:15]=[O:16])[CH:12]=2)[NH:7][N:6]=1)=[O:4]

参加物

7

反応物 2

HCID 12689298Methyl 5-bromo-1H-indazole-3-carboxylateHCID 178526064HCID 178526064、化合物

生成物 1

HCID 24958745methyl 5-formyl-1H-indazole-3-carboxylate収率 54%

試薬・触媒・溶媒 4

HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 5-bromo-1H-indazole-3-carboxylic acid methyl ester (1 g, 3.92 mmol), HCOONa (400 mg, 5.88 mmol), and PdCl2(PPh3)2 (138 mg, 0.2 mmol) in DMF (10 mL) was put under vacuum, and charged with CO. This process was repeated three times, and the mixture was kept at 110° C. for 6 hr. The reaction mixture was cooled to rt, diluted with EtOAc and water, and extracted. The organic phase was dried and concentrated. Purification via flash chromatography afforded 5-formyl-1H-indazole-3-carboxylic acid methyl ester (430 mg, 54%).

後処理

  1. additioncharged with CO
  2. extractionextracted
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. customPurification via flash chromatography

出典と根拠

ORDレコード
ord-ad5e6f2faee44796820de143999deeae
出典データセット
uspto-grants-2012_06
特許番号
US08198456B2

関連ノート

読み込み中…