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

HRID 1401110노트

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HRID 1401110 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8028Tetrahydrofuran용매

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온도
180 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2419ef62c3e9457e8cefa041ff8bd9bf
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08907093B2

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