3,5-Dimethylpyrazole → 1-(3-Methoxyphenyl)-3,5-dimethyl-1H-pyrazole

HRID 1509644노트

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HRID 1509644 반응식
I[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=1.[CH3:10][C:11]1[CH:15]=[C:14]([CH3:16])[NH:13][N:12]=1.C([O-])([O-])=O.[K+].[K+].[C@@H]1(N)CCCC[C@H]1N>O1CCOCC1.[Cu]I>[CH3:9][O:8][C:4]1[CH:3]=[C:2]([N:12]2[C:11]([CH3:10])=[CH:15][C:14]([CH3:16])=[N:13]2)[CH:7]=[CH:6][CH:5]=1

참가 물질

7

반응물 4

HCID 62103,5-DimethylpyrazoleHCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 69839Benzene, 1-iodo-3-methoxy-

생성물 1

HCID 392404991-(3-Methoxyphenyl)-3,5-dimethyl-1H-pyrazole

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 312751,4-Dioxane용매

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온도
110 °C

실험 절차

A mixture of 1-iodo-3-methoxybenzene (7.15 mL, 60 mmol, 1.0 eq), 3,5-dimethyl-1H-pyrazole (6.92 g, 72 mmol, 1.2 eq), CuI (0.46 g, 2.4 mmol, 0.04 eq), K2CO3 (17.41 g, 126 mmol, 2.1 eq), trans-1,2-cyclohexanediamine (1.37 g, 12 mmol, 0.2 eq) in dioxane (45 mL) was stirred at a temperature of 110° C. for 3.5 days under a nitrogen atmosphere and then cooled to ambient temperature. The solid was filtered off and washed with ethyl acetate. The filtrate was concentrated under reduced pressure and the residue was purified through column chromatography on silica gel using hexane and ethyl acetate (10:1-3:1) as an eluent to obtain the desired product, 1-(3-methoxyphenyl)-3,5-dimethyl-1H-pyrazole 1, as a brown liquid (7.12 g in 59% yield). 1H NMR (DMSO-d6, 400 MHz): δ 2.18 (s, 3H), 2.30 (s, 3H), 3.80 (s, 3H), 6.06 (s, 1H), 6.95 (dd, J=8.0, 2.4 Hz, 1H), 7.02-7.06 (m, 2H), 7.39 (t, J=8.0 Hz, 1H).

후처리

  1. temperaturecooled to ambient temperature
  2. filtrationThe solid was filtered off
  3. washwashed with ethyl acetate
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified through column chromatography on silica gel

출처 및 근거

ORD 기록
ord-92c650b15e8945a19bc63890d306cb3e
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09224963B2

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