Isoamyl nitrate → Methyl 4-iodo-1H-indazole-6-carboxylate

HRID 59802

반응식

HRID 59802 반응식
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([I:10])[C:7]([CH3:11])=[C:6]([NH2:12])[CH:5]=1.[N+:14]([O-])(OCCC(C)C)=O>C(O)(=O)C>[CH3:1][O:2][C:3]([C:4]1[CH:5]=[C:6]2[C:7]([CH:11]=[N:14][NH:12]2)=[C:8]([I:10])[CH:9]=1)=[O:13]

참가 물질

4

반응물 2

HCID 10985Isoamyl nitrateHCID 67512060HCID 67512060, 화합물

생성물 1

HCID 24728119Methyl 4-iodo-1H-indazole-6-carboxylate수율 91%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

To a solution of 3-amino-5-iodo-4-methyl-benzoic acid methyl ester (1.22 g, 4.21 mmol) in acetic acid (20 mL) was added isoamyl nitrate (0.675 mL, 4.63 mmol). The mixture was stirred at room temperature for 30 minutes and then concentrated under reduced pressure. The residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The organic layer was separated, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography to give 1.15 g (91%) of 4-iodo-1H-indazole-6-carboxylic acid methyl ester, MS (M+H)=303.

후처리

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-70809c7613524ef497c67b64df382b7e
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440956B2

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