Potassium Carbonate → 4-Methylphenyl 4-[(5-chloro-6-isopropoxypyridin-3-yl)oxy]-2,5-difluorobenzoate

HRID 2048040ノート

反応式

HRID 2048040 の反応式
[F:1][C:2]1[CH:17]=[C:16](F)[C:15]([F:19])=[CH:14][C:3]=1[C:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1)=[O:5].C(=O)([O-])[O-].[K+].[K+].[Cl:26][C:27]1[CH:28]=[C:29]([OH:37])[CH:30]=[N:31][C:32]=1[O:33][CH:34]([CH3:36])[CH3:35]>CS(C)=O>[Cl:26][C:27]1[CH:28]=[C:29]([O:37][C:16]2[C:15]([F:19])=[CH:14][C:3]([C:4]([O:6][C:7]3[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=3)=[O:5])=[C:2]([F:1])[CH:17]=2)[CH:30]=[N:31][C:32]=1[O:33][CH:34]([CH3:35])[CH3:36]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 580424084-Methylphenyl 2,4,5-trifluorobenzoateHCID 580424365-Chloro-6-isopropoxypyridin-3-OL

生成物 1

HCID 580424044-Methylphenyl 4-[(5-chloro-6-isopropoxypyridin-3-yl)oxy]-2,5-difluorobenzoate収率 166.1%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

4-Methylphenyl 2,4,5-trifluorobenzoate (Preparation 12, 1.00 g, 3.54 mmol) and potassium carbonate (1.66 g, 12.04 mmol) were suspended in DMSO (24 mL). 5-chloro-6-isopropoxypyridin-3-ol (Preparation 15, 651 mg, 3.47 mmol) was added portionwise over 5 minutes. The mixture was stirred at room temperature for 60 minutes, then partitioned between water (100 mL) and EtOAc (2×75 mL). The combined organics were dried over sodium sulfate, filtered and concentrated in vacuo to afford a green oil (2.5 g) which crystallised on standing. The solid was triturated with heptane to afford the title compound as a colourless solid (1.01 g, 65%):

後処理

  1. custompartitioned between water (100 mL) and EtOAc (2×75 mL)
  2. dry with materialThe combined organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-2f8c93d1f7a5446c91f3a8e872a65aa2
出典データセット
uspto-grants-2013_11
特許番号
US08592629B2

反応ノート

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