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

HRID 218460

反応式

HRID 218460 の反応式
I[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:13]([O:15][CH3:16])[CH3:14])=[O:12].[CH:17](O[Na])=[O:18]>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>[CH:17]([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:13]([O:15][CH3:16])[CH3:14])=[O:12])=[O:18]

参加物

6

反応物 2

HCID 205807385-iodo-N-methoxy-N-methyl-1H-indazole-3-carboxamideHCID 178526064HCID 178526064、化合物

生成物 1

HCID 249587435-formyl-N-methoxy-N-methyl-1H-indazole-3-carboxamide収率 15.6%

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-iodo-N-methoxy-N-methyl-1H-indazole-3-carboxamide (5 g, 15.1 mmol), HCOONa (1.85 g, 30.2 mmol), and PdCl2(PPh3)2 (320 mg, 0.453 mmol) in DMF (20 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. After cooling to 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 5-formyl-N-methoxy-N-methyl-1H-indazole-3-carboxamide (550 mg, 15.6%) as a white solid.

後処理

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

出典と根拠

ORDレコード
ord-0b44a3f09b694ce1b9e28c3b5e4698c1
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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