Phosphorus oxybromide → pentyl 3-bromo-1-(3-chloro-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxylate

HRID 1641453

반응식

HRID 1641453 반응식
[Cl:1][C:2]1[C:3]([N:8]2[CH:12]([C:13]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:14])[CH2:11][C:10](=O)[NH:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.P(Br)(Br)([Br:24])=O.C(=O)([O-])O.[Na+]>C(#N)C>[Br:24][C:10]1[CH2:11][CH:12]([C:13]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:14])[N:8]([C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=2)[N:9]=1

참가 물질

5

반응물 3

HCID 24613Phosphorus oxybromideHCID 516892Sodium BicarbonateHCID 59549450Pentyl 2-(3-chloro-2-pyridinyl)-5-oxopyrazolidine-3-carboxylate

생성물 1

HCID 59549455pentyl 3-bromo-1-(3-chloro-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxylate수율 137.5%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixed solution comprising 1.2 g of pentyl 2-(3-chloropyridin-2-yl)-5-oxopyrazolidine-3-carboxylate, 0.59 g of phosphorus oxybromide and 18 ml of acetonitrile was gradually heated, and 25 minutes later, the mixed solution was refluxed with heating for one hour. After the reaction liquid was stood to cool, it was slowly added to a saturated sodium hydrogen carbonate aqueous solution, followed by stirring for 5 minutes. The mixed liquid was subjected to extraction with ethyl acetate, and the organic layer was washed with a sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1 to 8/2) to obtain 1.06 g of the desired product (melting point: 39 to 42° C.) in the form of pale yellow crystals.

후처리

  1. temperaturewas gradually heated
  2. temperature25 minutes later, the mixed solution was refluxed
  3. temperaturewith heating for one hour
  4. customAfter the reaction liquid
  5. temperatureto cool
  6. extractionThe mixed liquid was subjected to extraction with ethyl acetate
  7. washthe organic layer was washed with a sodium chloride aqueous solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1 to 8/2)

출처 및 근거

ORD 기록
ord-b47c9ea67e0f4747a6b5cd6689948e58
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08115006B2

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