Cesium carbonate → 2-[(1-Methyl-1H-pyrazol-5-yl)methoxy]-5-(trifluoromethyl)pyridine

HRID 238392

反応式

HRID 238392 の反応式
[CH3:1][N:2]1[C:6]([CH2:7][OH:8])=[CH:5][CH:4]=[N:3]1.Cl[C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][N:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(P(C(C)(C)C)C1C=CC2C(=CC=CC=2)C=1C1C2C(=CC=CC=2)C=CC=1)(C)(C)C>C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH3:1][N:2]1[C:6]([CH2:7][O:8][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][N:11]=2)=[CH:5][CH:4]=[N:3]1

参加物

8

反応物 4

HCID 10796Cesium carbonateHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 2734941(1,1'-Binaphthalen)-2-yldi-tert-butylphosphineHCID 11815316(1-methyl-1H-pyrazol-5-yl)methanol

生成物 1

HCID 866848882-[(1-Methyl-1H-pyrazol-5-yl)methoxy]-5-(trifluoromethyl)pyridine収率 67.6%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
100 °C

実験手順

Under a nitrogen atmosphere, a mixture of (1-methyl-1H-pyrazol-5-yl)methanol (200 mg), 2-chloro-5-(trifluoromethyl)pyridine (389 mg), palladium(II) acetate (40 mg), cesium carbonate (870 mg), rac-2-(di-t-butylphosphino)-1,1′-binaphthyl (71 mg) and toluene (9.0 mL) was stirred at 100° C. for 2.5 hours. Thereafter, the reaction solution was diluted with diethyl ether, and was then filtrated with Celite. The filtrate was concentrated under a reduced pressure. The residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=85:15 to 50:50), so as to obtain the title compound (310 mg) in the form of a light yellow oily substance.

後処理

  1. filtrationwas then filtrated with Celite
  2. concentrationThe filtrate was concentrated under a reduced pressure
  3. customThe residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=85:15 to 50:50)

出典と根拠

ORDレコード
ord-8c6de477712d45f29b5d77c8d2732461
出典データセット
uspto-grants-2014_02
特許番号
US08642626B2

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