Potassium Carbonate → 1-(4-Chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethanol

HRID 1620395ノート

反応式

HRID 1620395 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:13])[C:9]([F:12])([F:11])[F:10])=[C:4](I)[CH:3]=1.[CH3:15][C:16]1[CH:20]=[CH:19][NH:18][N:17]=1.C([O-])([O-])=O.[K+].[K+].CN[C@@H]1CCCC[C@H]1NC>C(OCC)(=O)C.[Cu]I.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:13])[C:9]([F:12])([F:11])[F:10])=[C:4]([N:18]2[CH:19]=[CH:20][C:16]([CH3:15])=[N:17]2)[CH:3]=1

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 667436381-(4-Chloro-2-iodo-phenyl)-2,2,2-trifluoro-ethanolHCID 178428694HCID 178428694、化合物

生成物 1

HCID 252124151-(4-Chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethanol収率 33%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
130 °C

実験手順

1-(4-Chloro-2-iodo-phenyl)-2,2,2-trifluoro-ethanol (0.840 g, 2.5 mmol), 3-methyl pyrazole (0.230 g, 2.8 mmol), CuI (0.190 g, 1.0 mmol), K2CO3 (0.863 g, 6.25 mmol), (1R,2R)—N,N′-dimethyl-cyclohexane-1,2-diamine (0.071 g, 0.5 mmol) and toluene (10 ml) were combined in a 20 ml pressure tube, and the mixture was heated at 130° C. (oil bath temperature) for 12 hours. The mixture was diluted with ethyl acetate and washed with H2O (2×20 ml), brine, and dried over sodium sulfate. Removal of solvent gave a crude product, which was purified by ISCO column chromatography using 5-10% ethyl acetate in hexane as solvent to afford 1-[4-chloro-2-(3-methyl-pyrazol-1-yl)-phenyl]-2,2,2-trifluoro-ethanol (240 mg).

後処理

  1. washwashed with H2O (2×20 ml), brine
  2. dry with materialdried over sodium sulfate
  3. customRemoval of solvent
  4. customgave a crude product, which
  5. customwas purified by ISCO column chromatography

出典と根拠

ORDレコード
ord-dabc1c9decf945559a02fcabd74889e9
出典データセット
uspto-grants-2014_07
特許番号
US08772483B2

反応ノート

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