Carbazole → 9-(pyridin-2-yl)-9H-carbazole

HRID 716595ノート

反応式

HRID 716595 の反応式
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Br[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=C(C3C(OC)=CC=CC=3OC)C=CC=2)CCCCC1>[N:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[N:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2

参加物

7

反応物 3

HCID 6854CarbazoleHCID 79732-BromopyridineHCID 23676156Sodium t-butoxide

生成物 1

HCID 101017639-(pyridin-2-yl)-9H-carbazole収率 83%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 58401078Dicyclohexyl(2',6'-dimethoxybiphenyl-3-yl)phosphine触媒HCID 1140Toluene溶媒

実験手順

9-H-carbazole (20 g, 120 mmol), and 2-bromopyridine (13 mL, 132 mmol) were mixed in dry toluene (500 mL). The solution was bubbled nitrogen while stirring for 15 min. Pd2(dba)3 (0.6 g, 0.66 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-3-yl)phosphine (1 g, 0.24 mmol) and sodium tert-butoxide (20 g, 200 mmol) were added in sequence. The mixture was heated to reflux overnight under nitrogen. After cooling, the reaction mixture was filtered through Celite®/silica pad and the solvent was then evaporated. The residue was then purified by silica gel column chromatography using toluene:hexane (1:1, v/v) as eluent to obtain 24.3 g (83%) of the desired product.

後処理

  1. customThe solution was bubbled nitrogen
  2. temperatureThe mixture was heated
  3. temperatureto reflux overnight under nitrogen
  4. temperatureAfter cooling
  5. filtrationthe reaction mixture was filtered through Celite®/silica pad
  6. customthe solvent was then evaporated
  7. customThe residue was then purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-e345933cea7f41158abcb3b2a159293b
出典データセット
uspto-grants-2015_11
特許番号
US09190623B2

反応ノート

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