Diethyl Ether → 2-(1H-Pyrazol-3-Yl)Pyridine

HRID 650482

반응식

HRID 650482 반응식
Cl[C:2]1[C:3]([C:9]2[CH:13]=[C:12](C(F)(F)F)[NH:11][N:10]=2)=[N:4][CH:5]=[C:6](Cl)[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].CI.C(OCC)C>CN1CCCC1=O.O>[N:4]1[CH:5]=[CH:6][CH:7]=[CH:2][C:3]=1[C:9]1[NH:10][N:11]=[CH:12][CH:13]=1

참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21712162HCID 21712162, 화합물

생성물 1

HCID 27976572-(1H-Pyrazol-3-Yl)Pyridine수율 86.6%

시약·촉매·용매 2

HCID 962Water용매HCID 13387N-methyl-2-pyrrolidone용매2회

반응 조건

온도
55 °C

실험 절차

8.88 g of 3-(3,5-dichloro-2-pyridyl)-5-trifluoromethyl-[1H]-pyrazole (Example P10) are introduced into 35 ml of N-methylpyrrolidone. After the addition of 13.0 g of potassium carbonate, the mixture is stirred and heated to 55° C. 2.36 ml of methyl iodide in 5.0 ml of N-methylpyrrolidone are then slowly added dropwise. After subsequently stirring for 2 hours, diethyl ether and water are added, the mixture is extracted by shaking and the organic phase is separated off. The separated ethereal phase is washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product is purified by means of flash chromatography (silica gel; eluant: toluene/ethyl acetate 100/1). First of all 3.96 g of the 5-pyridylpyrazole isomer (yield 42%) are isolated in the form of a yellow oil and then 1.96 g of the 3-pyridylpyrazole (yield 21%) are isolated in the form of a yellow solid. The Rf values of the 3- and 5-pyridylpyrazole isomers on silica gel 60 F254 using toluene/ethyl acetate 30/1 as eluant (UV) are:

후처리

  1. stirringAfter subsequently stirring for 2 hours
  2. extractionthe mixture is extracted
  3. stirringby shaking
  4. customthe organic phase is separated off
  5. washThe separated ethereal phase is washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product is purified by means of flash chromatography (silica gel; eluant: toluene/ethyl acetate 100/1)

출처 및 근거

ORD 기록
ord-092cbf3cb2f146188c66b0197eb7263b
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06274536B1

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