Dimethylformamide → 1-Methyl-5-{[4-(trifluoromethyl)phenyl]ethynyl}-1H-pyrazole

HRID 238360노트

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HRID 238360 반응식
I[C:2]1[N:6]([CH3:7])[N:5]=[CH:4][CH:3]=1.[C:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1)#[CH:9].C(N(CC)CC)C.CN(C)C=O>[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH3:7][N:6]1[C:2]([C:9]#[C:8][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:12][CH:11]=2)=[CH:3][CH:4]=[N:5]1

참가 물질

9

반응물 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 43482951-Ethynyl-4-(trifluoromethyl)benzeneHCID 133340655-Iodo-1-methyl-1H-pyrazole

생성물 1

HCID 866848631-Methyl-5-{[4-(trifluoromethyl)phenyl]ethynyl}-1H-pyrazole수율 80.5%

시약·촉매·용매 4

HCID 11776Triphenylphosphine촉매HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매

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온도
75 °C

실험 절차

A mixture of 5-iodo-1-methyl-1H-pyrazole (8.00 g), 1-ethynyl-4-(trifluoromethyl)benzene (6.54 g), copper(I) iodide (110 mg), bis(triphenylphosphine)palladium(II) dichloride (1.35 g), triphenylphosphine (504 mg), triethylamine (8.00 mL) and dimethylformamide (70 mL) was stirred at 75° C. for 2 hours. Thereafter, the reaction solution was added to water, and the obtained mixture was then extracted with ethyl acetate. The organic layer was successively washed with water and a saturated saline, and was then dried over anhydrous magnesium sulfate, followed by vacuum concentration. The residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=85:15 to 75:25), so as to obtain the title compound (7.74 g) in the form of a yellow solid.

후처리

  1. extractionthe obtained mixture was then extracted with ethyl acetate
  2. washThe organic layer was successively washed with water
  3. dry with materiala saturated saline, and was then dried over anhydrous magnesium sulfate
  4. concentrationfollowed by vacuum concentration
  5. customThe residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=85:15 to 75:25)

출처 및 근거

ORD 기록
ord-2746452428f0474e8b37d0e24d47a569
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642626B2

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