Pyrazole → 7-nitro-3-(1H-pyrazol-1-yl)quinoline

HRID 1620080노트

반응식

HRID 1620080 반응식
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[Cs+].[Cs+].CC1N(C(N(C)C)=O)C1.I[C:32]1[CH:33]=[N:34][C:35]2[C:40]([CH:41]=1)=[CH:39][CH:38]=[C:37]([N+:42]([O-:44])=[O:43])[CH:36]=2>[Cu](I)I.O>[N+:42]([C:37]1[CH:36]=[C:35]2[C:40]([CH:41]=[C:32]([N:1]3[CH:5]=[CH:4][CH:3]=[N:2]3)[CH:33]=[N:34]2)=[CH:39][CH:38]=1)([O-:44])=[O:43]

참가 물질

8

반응물 5

HCID 1048PyrazoleHCID 10796Cesium carbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 11007919N,N,2-trimethylaziridine-1-carboxamideHCID 686188213-Iodo-7-nitroquinoline

생성물 1

HCID 686188247-nitro-3-(1H-pyrazol-1-yl)quinoline수율 99.9%

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 962Water용매

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온도
70 °C

실험 절차

Pyrazole (20 mg), trans-N,N′-dimethylcyclohexane-1,2-diamine (24 μl), copper iodide (14 mg), and cesium carbonate (73 mg) were added to an N,N-dimethylpropyleneurea (2 ml) solution containing 3-iodo-7-nitroquinoline (45 mg), followed by stirring at 70° C. for 2.5 hours in a nitrogen atmosphere. Water was added to the reaction solution, an insoluble precipitate was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0 to 0:1), and a light yellow solid of 7-nitro-3-(1H-pyrazol-1-yl)quinoline (36 mg) was thus obtained.

후처리

  1. customan insoluble precipitate was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0 to 0:1)

출처 및 근거

ORD 기록
ord-1ac6946055fb40419e48813c82999e84
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772320B2

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