Methanol → Methyl 6-bromo-1H-indazole-3-carboxylate

HRID 1398601노트

반응식

HRID 1398601 반응식
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([OH:13])=[O:12])=[N:7][NH:8]2)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:18]O>>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([O:13][CH3:18])=[O:12])=[N:7][NH:8]2)=[CH:4][CH:3]=1

참가 물질

4

반응물 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 247280286-Bromo-1H-indazole-3-carboxylic acid

생성물 1

HCID 46784006Methyl 6-bromo-1H-indazole-3-carboxylate

반응 조건

온도
60 °C

실험 절차

To a solution of 6-bromo-1H-indazole-3-carboxylic acid (1.5 g, 6.22 mmol) in methanol (25 mL) was added thionyl chloride (2.26 ml, 31.12 mmol). The mixture was heated at 60° C. for 1 hr. The reaction mixture was cooled and concentrated in vacuo. The crude residue was dissolved in EtOAc (30 mL) and washed with saturated aqueous NaHCO3 (10 mL), water (10 mL) and dried (Na2SO4), filtered and concentrated in vacuo to give the title intermediate: 1H NMR (500 MHz, CDCl3) delta 4.08 (3H, s), 7.44 (1H, d, J=8.6 Hz), 7.89 (1H, s), 8.09 (1H, d, J=8.7 Hz), 11.70 (1H, s); LC-MS: m/z=+254.85/256.75 (M+H)+.

후처리

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated in vacuo
  3. dissolutionThe crude residue was dissolved in EtOAc (30 mL)
  4. washwashed with saturated aqueous NaHCO3 (10 mL), water (10 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-94d526991b4c4205b3f20f1c5dce0eae
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901313B2

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