1,4-Diaminocyclohexane → 2-bromo-9-(pyridin-2-yl)-9H-carbazole

HRID 64543

반응식

HRID 64543 반응식
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[NH:5][C:4]=2[CH:3]=1.I[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1C(N)CCC(N)C1>[Cu](I)I.O.O1CCOCC1>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[C:4]=2[CH:3]=1

참가 물질

8

반응물 4

HCID 183741,4-DiaminocyclohexaneHCID 62657Potassium Phosphate, TribasicHCID 2211262-IodopyridineHCID 127170892-Bromo-9H-carbazole

생성물 1

HCID 706548522-bromo-9-(pyridin-2-yl)-9H-carbazole수율 43.2%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
65 °C

실험 절차

A 100 mL 3-neck flask was charged with copper iodide (0.057 g, 0.301 mmol), 2-bromo-9H-carbazole (7.4 g, 30.1 mmol), 2-iodopyridine (12.3 g, 60.1 mmol), potassium phosphate (12.8 g, 60.1 mmol), (1R,4R)-cyclohexane-1,4-diamine (0.343 g, 3.0 mmol), and dioxane (25 mL) and the reaction mixture was heated at 65° C. for 16 hours. The reaction mixture was then poured into deionized water and extracted with dichloromethane The organic layers were combined and subjected to a column chromatography (neutral Al2O3, 99/1 hexane/EtOAc) to yield 4.2 g (43%) of 2-bromo-9-(pyridin-2-yl)-9H-carbazole as a white solid. The product was confirmed by GC/MS and NMR.

후처리

  1. extractionextracted with dichloromethane The organic layers

출처 및 근거

ORD 기록
ord-025f65fadd3e46f68e5821f6da41c4a5
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09450195B2

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