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

HRID 218460

반응식

HRID 218460 반응식
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]

참가 물질

6

반응물 2

HCID 205807385-iodo-N-methoxy-N-methyl-1H-indazole-3-carboxamideHCID 178526064HCID 178526064, 화합물

생성물 1

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

시약·촉매·용매 3

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0b44a3f09b694ce1b9e28c3b5e4698c1
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198456B2

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