Potassium Carbonate → 4-[(5-Chloro-6-isobutoxypyridin-3-yl)oxy]-3-cyanobenzoic acid

HRID 2048035ノート

反応式

HRID 2048035 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([OH:13])[CH:5]=[N:6][C:7]=1[O:8][CH2:9][CH:10]([CH3:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+].[C:20]([C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][C:30]=1F)[C:25]([OH:27])=[O:26])#[N:21]>CS(C)=O.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([O:13][C:30]2[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][C:22]=2[C:20]#[N:21])[CH:5]=[N:6][C:7]=1[O:8][CH2:9][CH:10]([CH3:11])[CH3:12]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 27739323-Cyano-4-fluorobenzoic acidHCID 580425005-Chloro-6-isobutoxypyridin-3-OL

生成物 1

HCID 580424824-[(5-Chloro-6-isobutoxypyridin-3-yl)oxy]-3-cyanobenzoic acid収率 120%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

5-Chloro-6-isobutoxypyridin-3-ol (Preparation 16, 0.124 g, 0.62 mmol) and potassium carbonate (0.28 g, 2.03 mmol) were suspended in DMSO (3.0 mL). Then 3-cyano-4-fluorobenzoic acid (0.0835 g, 0.51 mmol) was added portionwise. The reaction was then stirred at 90° C. under nitrogen for 16 hours, diluted in EtOAc (15 mL) and washed twice with an aqueous solution of HCl (2.0 M, 10 mL). The organic layer was then dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by reverse phase column chromatography (ISCO®, gradient of 5-95% acetonitrile in water, 13 g C18 column) to afford the title compound as an orange oil (0.21 g, 120%):

後処理

  1. washwashed twice with an aqueous solution of HCl (2.0 M, 10 mL)
  2. dry with materialThe organic layer was then dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by reverse phase column chromatography (ISCO®, gradient of 5-95% acetonitrile in water, 13 g C18 column)

出典と根拠

ORDレコード
ord-7eb14b30670e47ebbdadcf893d4c3dba
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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