Pentanochlor → 3,6-dibromo-9-((oxiran-2-yl)methyl)-9H-carbazole

HRID 555312

反応式

HRID 555312 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=3.CC[CH2:18][CH:19]([C:21](NC1C=CC(C)=C(Cl)C=1)=[O:22])C>C1(C)C=CC=CC=1>[Br:15][C:10]1[CH:9]=[CH:8][C:7]2[N:6]([CH2:18][CH:19]3[CH2:21][O:22]3)[C:5]3[C:13]([C:12]=2[CH:11]=1)=[CH:14][C:2]([Br:1])=[CH:3][CH:4]=3

参加物

4

反応物 2

HCID 16826PentanochlorHCID 2748743,6-Dibromocarbazole

生成物 1

HCID 27754733,6-dibromo-9-((oxiran-2-yl)methyl)-9H-carbazole収率 60%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

At rt under an inert atmosphere, (±)-glycyclol (0.129 g, 1.74 mmol, 120 uL) is added into a solution of 3,6-dibromo-9-H-carbazole (0.565 g, 1.74 mmol) in anhydrous toluene (10 mL). Then CMMP (which is prepared according to the protocol of Tetsuto, Tsunoda Tett. Lett. 1996, 37(14), 2459-2462) (0.20 g, 1.74 mmol) is added. The resulting mixture is allowed to stir at rt for 16 hours. The solvent is evaporated and the crude compound is purified via flash chromatography using Biotage device and Petroleum Ether/DCM (3/1) as eluant to give the title compound in a 60% yield as a white solid and 5% of (±)-3,6-dibromo-9-[(1E)-3-(3,6-dibromocarabazol-9-yl)propen-1-enyl]carbazole as a grey powder.

後処理

  1. addition1996, 37(14), 2459-2462) (0.20 g, 1.74 mmol) is added
  2. customThe solvent is evaporated
  3. customthe crude compound is purified via flash chromatography

出典と根拠

ORDレコード
ord-925c7a70393742c09029a372f624778c
出典データセット
uspto-grants-2011_11
特許番号
US08053436B1

関連ノート

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