Hydrochloric Acid → 6-Chloro-2-(4-methoxy-3,5-dimethylphenyl)oxazolo[4,5-C]pyridine

HRID 1401110ノート

反応式

HRID 1401110 の反応式
N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl.Cl[C:23]1[CH:28]=[C:27]([Cl:29])[N:26]=[CH:25][C:24]=1[NH:30][C:31](=[O:42])[C:32]1[CH:37]=[C:36]([CH3:38])[C:35]([O:39][CH3:40])=[C:34]([CH3:41])[CH:33]=1>O1CCCC1.[Cu]I>[Cl:29][C:27]1[N:26]=[CH:25][C:24]2[N:30]=[C:31]([C:32]3[CH:37]=[C:36]([CH3:38])[C:35]([O:39][CH3:40])=[C:34]([CH3:41])[CH:33]=3)[O:42][C:23]=2[CH:28]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 86675964N-(4,6-Dichloropyridin-3-yl)-4-methoxy-3,5-dimethylbenzamide

生成物 1

HCID 717431286-Chloro-2-(4-methoxy-3,5-dimethylphenyl)oxazolo[4,5-C]pyridine

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
180 °C

実験手順

In a microwaveable vessel, 0.98 g of N-(4,6-dichloropyridin-3-yl)-4-methoxy-3,5-dimethylbenzamide were dissolved in 15 ml of dry tetrahydrofuran, and 29 mg of copper(I) iodide, 54 mg of 1,10-phenanthroline and 1.47 g of cesium carbonate were added. In a microwave sunthesizer, the reaction mixture was then heated at 180° C. for 3 h. For work-up, the mixture was added to 12 ml of a 0.5 M aqueous hydrochloric acid solution. The precipitated solid was filtered off with suction and the mother liquor was extracted twice with ethyl acetate. The collected organic phases were combined with the suction-filtered solid and the solvent was removed under reduced pressure. This gave 0.79 g (91%) of the product, which was reacted further without any further purification.

後処理

  1. filtrationThe precipitated solid was filtered off with suction
  2. extractionthe mother liquor was extracted twice with ethyl acetate
  3. customthe solvent was removed under reduced pressure
  4. customThis gave 0.79 g (91%) of the product, which was reacted further without any further purification

出典と根拠

ORDレコード
ord-2419ef62c3e9457e8cefa041ff8bd9bf
出典データセット
uspto-grants-2014_12
特許番号
US08907093B2

反応ノート

読み込み中…