Cesium fluoride → Methyl 5-bromo-2-fluoropyridine-3-carboxylate

HRID 1986093노트

반응식

HRID 1986093 반응식
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[F-:13].[Cs+]>CS(C)=O.O>[Br:1][C:2]1[CH:3]=[N:4][C:5]([F:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

참가 물질

5

반응물 2

HCID 25953Cesium fluorideHCID 2763343Methyl 5-bromo-2-chloronicotinate

생성물 1

HCID 45588056Methyl 5-bromo-2-fluoropyridine-3-carboxylate수율 57%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

To a solution of methyl 5-bromo-2-chloronicotinate (170 mg, 0.68 mmol) in 3 mL of DMSO was added CsF (152 mg, 1.0 mmol). The solution was stirred at room temperature for 2 d and then heated at 60° C. for 4 h. After cooling, the mixture was diluted with 30 mL of H2O. The aqueous solution was extracted with EtOAc and the combined organic layers were washed with brine, and dried over MgSO4. After filtration and concentration in vacuo, the residue was purified by silica gel flash chromatography to give the desired product (90 mg, 57% yield). MS (ESI+) m/z 234.06, 236.09 (M+H)+.

후처리

  1. temperatureheated at 60° C. for 4 h
  2. temperatureAfter cooling
  3. extractionThe aqueous solution was extracted with EtOAc
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration and concentration in vacuo
  7. customthe residue was purified by silica gel flash chromatography

출처 및 근거

ORD 기록
ord-fb0ccce1bc1a4da6869dc440824044df
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07547782B2

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