Sodium hydride → 3-chloro-1-(cyclopropylmethyl)-5-methoxypyridazin-4(1H)-one

HRID 1747812노트

반응식

HRID 1747812 반응식
[Cl:1][C:2]1[N:3]=[N:4][CH:5]=[C:6]([O:9][CH3:10])[C:7]=1[OH:8].[H-].[Na+].Br[CH2:14][CH:15]1[CH2:17][CH2:16]1>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Cl:1][C:2]1[C:7](=[O:8])[C:6]([O:9][CH3:10])=[CH:5][N:4]([CH2:14][CH:15]2[CH2:17][CH2:16]2)[N:3]=1

참가 물질

7

반응물 3

HCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 178493809HCID 178493809, 화합물

생성물 1

HCID 895861593-chloro-1-(cyclopropylmethyl)-5-methoxypyridazin-4(1H)-one

시약·촉매·용매 3

HCID 67553Tetrabutylammonium Iodide촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

3-Chloro-5-methoxypyridazin-4-ol (0.20 g) was dissolved in DMF (3.1 mL), NaH (0.0595 g, 60%, in oil) and tetrabutylammoniumiodide (0.0916 g) were added at 0° C., and the mixture was stirred at the same temperature for 30 min. To the reaction mixture was added (bromomethyl)cyclopropane (0.138 mL) at 0° C., and the mixture was stirred at 0° C. for 2.5 hr, at room temperature for 1 day and at 40° C. for 20 hr. The reaction mixture was diluted with water, extracted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography (ethyl acetate/hexane→methanol/ethyl acetate) to give the title compound (0.136 g).

후처리

  1. stirringthe mixture was stirred at 0° C. for 2.5 hr, at room temperature for 1 day and at 40° C. for 20 hr
  2. extractionextracted with ethyl acetate
  3. washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography (ethyl acetate/hexane→methanol/ethyl acetate)

출처 및 근거

ORD 기록
ord-ce6e91da4f2344778e44fd50e482bb17
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150588B2

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