Potassium Phosphate, Tribasic → 2-(3-Cyanoindol-1-yl)isonicotinic acid ethyl ester

HRID 73373

반응식

HRID 73373 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]#[N:11])=[CH:2]1.[CH2:12]([O:14][C:15](=[O:23])[C:16]1[CH:21]=[CH:20][N:19]=[C:18](Br)[CH:17]=1)[CH3:13].P([O-])([O-])([O-])=O.[K+].[K+].[K+].CN[C@@H]1CCCC[C@H]1NC>[Cu](I)I.C1(C)C=CC=CC=1>[CH2:12]([O:14][C:15](=[O:23])[C:16]1[CH:17]=[CH:18][N:19]=[C:20]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]([C:10]#[N:11])=[CH:2]2)[CH:21]=1)[CH3:13]

참가 물질

7

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 2302823-CyanoindoleHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 3847769Ethyl 2-bromoisonicotinate

생성물 1

HCID 584373112-(3-Cyanoindol-1-yl)isonicotinic acid ethyl ester수율 30.1%

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 1140Toluene용매

반응 조건

온도
110 °C

실험 절차

A mixture of 1H-indole-3-carbonitrile (0.1 g), 2-bromoisonicotinic acid ethyl ester (0.16 g), potassium phosphate (0.27 g), (1R,2R)-(−)-N,N′-dimethylcyclohexane-1,2-diamine (0.017 g), copper iodide (0.006 g) and toluene (0.7 mL) was stirred at 110° C. for 38 hours. The insoluble material was removed by filtration, and this filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=10/90 to 66/34) to give the title compound (0.061 g).

후처리

  1. customThe insoluble material was removed by filtration
  2. concentrationthis filtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=10/90 to 66/34)

출처 및 근거

ORD 기록
ord-953e4f3bddfc4af7bead9475e160251d
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829040B2

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