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

HRID 238360

反応式

HRID 238360 の反応式
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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 11776Triphenylphosphine触媒HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒

反応条件

温度
75 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-2746452428f0474e8b37d0e24d47a569
出典データセット
uspto-grants-2014_02
特許番号
US08642626B2

関連ノート

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