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

HRID 1958279

反応式

HRID 1958279 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, (±)-glycydol (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-fb42d97894d146edb393e3e2cb59e025
出典データセット
uspto-grants-2013_04
特許番号
US08410110B2

関連ノート

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