1-Propanol → Ethyl 5-methyl-1-{6-[2-(trifluoromethoxy)phenyl]pyridin-2-yl}-1H-pyrazole-3-carboxylate

HRID 733142노트

반응식

HRID 733142 반응식
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1B(O)O.Cl[C:16]1[N:21]=[C:20]([N:22]2[C:26]([CH3:27])=[CH:25][C:24]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[N:23]2)[CH:19]=[CH:18][CH:17]=1.C(O)CC.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH3:27][C:26]1[N:22]([C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[O:3][C:2]([F:14])([F:13])[F:1])[N:21]=2)[N:23]=[C:24]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:25]=1

참가 물질

6

반응물 4

HCID 10311-PropanolHCID 516892Sodium BicarbonateHCID 27772042-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride)HCID 57428255Ethyl 1-(6-chloropyridin-2-yl)-5-methyl-1h-pyrazole-3-carboxylate

생성물 1

HCID 11361317Ethyl 5-methyl-1-{6-[2-(trifluoromethoxy)phenyl]pyridin-2-yl}-1H-pyrazole-3-carboxylate수율 12.3%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
90 °C

실험 절차

To the solution of 2-trifluoromethoxyphenyl boronic acid (0.192 g, 0.92 mmol) and the 2-chloropyridine compound from Step 1 (0.165 g, 0.62 mmol) in toluene:n-propanol (3 mL:3 mL) were added tetrabis(triphenylphosphine)palladium (0.072 g, 0.062 mmol) and aqueous sodium bicarbonate (2.0M, 0.62 mL, 1.2 mmol). The reaction mixture was stirred at 90° C. for 16 hours. After cooling to room temperature, the mixture was filtered through a Celite pad, and washed with ethyl acetate (3 times). The filtrate was concentrated. The resulting residue was dissolved in ethyl acetate and washed with saturated sodium carbonate aqueous solution and brine, the organic layer was dried over anhydrous sodium sulfate. After concentration, the crude product was applied to column chromatography on silica gel to afford the titled compound, as yellow oil, 30 mg, 12.3% yield.

후처리

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture was filtered through a Celite pad
  3. washwashed with ethyl acetate (3 times)
  4. concentrationThe filtrate was concentrated
  5. dissolutionThe resulting residue was dissolved in ethyl acetate
  6. washwashed with saturated sodium carbonate aqueous solution and brine
  7. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  8. concentrationAfter concentration

출처 및 근거

ORD 기록
ord-085e1e85050440d6a9a675a51ea65a7d
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07589116B2

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