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

HRID 1047635노트

반응식

HRID 1047635 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9a524232e8d14a97b1e78e5c663309b2
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569512B2

반응 노트

불러오는 중…