Cesium carbonate → methyl 3-bromo-1H-indazole-6-carboxylate

HRID 1047635ノート

反応式

HRID 1047635 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[N:10][NH:11]2)=[CH:7][CH:6]=1)=[O:4].C(=O)([O-])[O-].[Cs+].[Cs+].[Br:20]Br>C(#N)C>[Br:20][C:9]1[C:8]2[C:12](=[CH:13][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=2)[NH:11][N:10]=1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 24408BromineHCID 286535methyl 1H-indazole-6-carboxylate

生成物 1

HCID 178497093methyl 3-bromo-1H-indazole-6-carboxylate収率 99%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

6-(1H)-indazole carboxylic acid methyl ester (1.5688 g, 8.90 mmol) and cesium carbonate (4.38 g, 13.44 mmol) were dissolved in acetonitrile (89 ml) at 25° C. Bromine (0.554 ml, 10.75 mmol) was added and the reaction mixture was allowed to stir for 20 min. The reaction was stopped, quenched by addition of saturated aqueous sodium hydrogen carbonate (30 mL) and 10% aqueous sodium thiosulfate (30 mL), and the mixture extracted with ethyl acetate (3×50 mL). The combined organic phases were washed with saturated aqueous sodium chloride (1×50 mL), dried (sodium sulfate), filtered, and the solvent evaporated under reduced pressure. The title compound (2.241 g, 8.79 mmol, 99% yield) was recovered as a light orange/white solid. LC-MS: [M+1]=255.2.

後処理

  1. customquenched by addition of saturated aqueous sodium hydrogen carbonate (30 mL) and 10% aqueous sodium thiosulfate (30 mL)
  2. extractionthe mixture extracted with ethyl acetate (3×50 mL)
  3. washThe combined organic phases were washed with saturated aqueous sodium chloride (1×50 mL)
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure

出典と根拠

ORDレコード
ord-9a524232e8d14a97b1e78e5c663309b2
出典データセット
uspto-grants-2013_10
特許番号
US08569512B2

反応ノート

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