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Cesium carbonate → 4-[2-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-benzonitrile

HRID 2261756
ノート
印刷プレビュー

反応式

HRID 2261756 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:13]([CH2:14][OH:15])=[C:12]([CH:16]([CH3:18])[CH3:17])[CH:11]=[N:10]1.F[C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[C:22]([CH3:28])[CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[N:9]1[C:13]([CH2:14][O:15][C:20]2[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[C:22]([CH3:28])[CH:21]=2)=[C:12]([CH:16]([CH3:18])[CH3:17])[CH:11]=[N:10]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 38260554-Fluoro-2-methylbenzonitrileHCID 57443256(1-(2,6-dichlorophenyl)-4-isopropyl-1H-pyrazol-5-yl)methanol

生成物 1

HCID 675281824-[2-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-benzonitrile収率 61%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To an ambient temperature solution of [2-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-yl]-methanol (2.50 g, 8.76 mmol) in DMF (15 mL) is added 4-Fluoro-2-methyl-benzonitrile 1.18 g, 8.76 mmol), cesium carbonate (5.71 g, 17.53 mmol). The reaction mixture is heated to 80° C. overnight. The reaction mixture is concentrated and the residue is partitioned between Et2O and water. The aqueous layer is extracted with Et2O and the combined organic layers are washed with brine, dried (MgSO4), filtered, concentrated, and chromatographed (0% to 20% EtOAc/Hex) to yield the title compound (2.13 g, 61%). 1H NMR (400 MHz, CDCl3) δ 7.72 (s, 1H), 7.46-7.40 (m, 3H), 7.32 (dd, 1H, J=9.0, 7.3 Hz), 6.68-6.62 (m, 2H), 4.85 (s, 2H), 2.99 (sept, 1H, J=7.0 Hz), 2.46 (s, 3H), 1.31 (d, 6H, J=7.0 Hz).

後処理

  1. concentrationThe reaction mixture is concentrated
  2. customthe residue is partitioned between Et2O and water
  3. extractionThe aqueous layer is extracted with Et2O
  4. washthe combined organic layers are washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed (0% to 20% EtOAc/Hex)

出典と根拠

ORDレコード
ord-84c3b8eceec94005bfa1a38e6b3ee970
出典データセット
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07846960B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート