Methanol → Methyl 5-bromo-1H-indazole-3-carboxylate

HRID 2367694노트

반응식

HRID 2367694 반응식
S(=O)(=O)(O)O.[Br:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[C:10]2[C:16]([OH:18])=[O:17].[CH3:19]O>>[Br:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[C:10]2[C:16]([O:18][CH3:19])=[O:17]

참가 물질

4

반응물 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 71573585-bromo-1H-indazole-3-carboxylic Acid

생성물 1

HCID 12689298Methyl 5-bromo-1H-indazole-3-carboxylate수율 98%

실험 절차

Concentrated sulfuric acid (1 mL) was added to a suspension of 5-bromo-1H-indazole-3-carboxylic acid (CXV) (1.30 g, 5.39 mmol) in dry MeOH (50 mL) and heated to reflux for 4 h under argon. The solution was cooled to room temperature and the MeOH was evaporated under vacuum. The residue was dissolved in EtOAc and washed with water. The organic phase was dried over Na2SO4, filtered and concentrated to afford methyl 5-bromo-1H-indazole-3-carboxylate (CXVI) as a white solid (1.35 g, 5.29 mmol, 98% yield). 1H NMR (DMSO-d6) δ ppm 14.13 (s, 1H), 8.21 (d, J=1.6 Hz, 1H), 7.67 (d, J=7.2 Hz, 1H), 7.59 (dd, J=7.2, 1.2 Hz, 1H), 3.92 (s, 3H); ESIMS found for C9H7BrN2O2 m/z 256.0 (M+H).

후처리

  1. temperatureheated
  2. temperatureto reflux for 4 h under argon
  3. customthe MeOH was evaporated under vacuum
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with water
  6. dry with materialThe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-94b742b432644fb89b2567024364bb95
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697887B2

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