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

HRID 1398601ノート

反応式

HRID 1398601 の反応式
[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

参加物

4

反応物 3

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

生成物 1

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

反応条件

温度
60 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-94d526991b4c4205b3f20f1c5dce0eae
出典データセット
uspto-grants-2014_12
特許番号
US08901313B2

反応ノート

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