1,2-Diaminocyclohexane, trans- → 9-(2'-nitrobiphenyl-4-yl)-2-(pyridin-2-yl)-9H-carbazole

HRID 1509634ノート

反応式

HRID 1509634 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:19]=[CH:18][C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[CH:8]=1.I[C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[N+:33]([O-:35])=[O:34])=[CH:23][CH:22]=1.[C@@H]1(N)CCCC[C@H]1N.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>ClCCl.CO.[Cu]I>[N+:33]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:24]1[CH:23]=[CH:22][C:21]([N:10]2[C:9]3[CH:8]=[C:7]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)[CH:19]=[CH:18][C:17]=3[C:16]3[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=3)=[CH:26][CH:25]=1)([O-:35])=[O:34]

参加物

7

反応物 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 6297494'-Iodo-2-nitrobiphenylHCID 222472152-(2-pyridyl)-9H-carbazole

生成物 1

HCID 1181139679-(2'-nitrobiphenyl-4-yl)-2-(pyridin-2-yl)-9H-carbazole収率 94.2%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 21226129Dichloromethane methanol溶媒

反応条件

温度
112.5 °C

実験手順

2-(Pyridin-2-yl)-9H-carbazole (611 mg, 2.5 mmol, 1.0 eq), 4′-iodo-2-nitrobiphenyl (975 mg, 3.0 mmol, 1.2 eq), CuI (48 mg, 0.25 mmol, 0.1 eq), trans-cyclohexane-1,2-diamine (250 uL, 2.5 mmol, 1.0 eq) and K3PO4 (1114 mg, 5.25 mmol, 2.1 eq) were added to a dry pressure vessel equipped with a magnetic stir bar. The vessel was evacuated and back-filled with nitrogen. The evacuation and back-fill procedure was repeated twice. Then solvent dioxane (10 mL) was added under nitrogen. After bubbling with nitrogen for 30 minutes, the mixture was stirred at 110-115° C. in an oil bath for 4 days. Then the mixture was cooled to ambient temperature. The solvent was removed under reduced pressure and the residue was purified through column chromatography on silica gel using hexane/ethyl acetate (10:1-3:1) then dichloromethane/methanol (20:1) as an eluent to obtain the desired product as a solid (1.04 g in 94% yield). 1H NMR (DMSO-d6, 400 MHz): δ 7.36 (t, J=6.0 Hz, 2H), 7.45 (d, J=8.0 Hz, 1H), 7.51 (d, J=8.4 Hz, 1H), 7.70-7.92 (m, 8H), 8.05 (t, J=8.4 Hz, 2H), 8.10 (d, J=8.4 Hz, 1H), 8.22 (s, 1H), 8.33 (d, J=7.2 Hz, 1H), 8.39 (d, J=8.0 Hz, 1H), 8.67 (d, J=4.8 Hz, 1H).

後処理

  1. customequipped with a magnetic stir bar
  2. customThe vessel was evacuated
  3. additionback-filled with nitrogen
  4. additionThen solvent dioxane (10 mL) was added under nitrogen
  5. customAfter bubbling with nitrogen for 30 minutes
  6. temperatureThen the mixture was cooled to ambient temperature
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified through column chromatography on silica gel

出典と根拠

ORDレコード
ord-f7a48549f2024f938bc1b880bdb3b337
出典データセット
uspto-grants-2015_12
特許番号
US09224963B2

反応ノート

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