Sodium hydride → 1,1'-{9-[2-(1-Methylpyrrolidin-2-yl)ethyl]-9H-carbazole-3,6-diyl}diethanone

HRID 514757

反応式

HRID 514757 の反応式
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][C:8]([C:14](=[O:16])[CH3:15])=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[C:3]([C:17](=[O:19])[CH3:18])[CH:2]=1.[H-].[Na+].Cl.Cl[CH2:24][CH2:25][CH:26]1[CH2:30][CH2:29][CH2:28][N:27]1[CH3:31].C(Cl)(Cl)Cl.CO>CN(C=O)C.O>[CH3:31][N:27]1[CH2:28][CH2:29][CH2:30][CH:26]1[CH2:25][CH2:24][N:12]1[C:13]2[CH:1]=[CH:2][C:3]([C:17](=[O:19])[CH3:18])=[CH:4][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[C:8]([C:14](=[O:16])[CH3:15])[CH:7]=2

参加物

7

反応物 4

HCID 24758Sodium hydrideHCID 2364861-(6-Acetyl-9H-carbazol-3-yl)-ethanoneHCID 3017050Pyrrolidine, 2-(2-chloroethyl)-1-methyl-, hydrochloride (1:1)HCID 21584188Chloroform methanol

生成物 1

HCID 453810131,1'-{9-[2-(1-Methylpyrrolidin-2-yl)ethyl]-9H-carbazole-3,6-diyl}diethanone収率 64.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

The diacetyl derivative 31 (0.97 g, 3.86 mmol) was dissolved in DMF (7 mL). NaH (0.54 g, 13.5 mmol) was added, and the mixture was stirred for 3-5 min at room temperature. 2-(2-Chloroethyl)-1-methylpyrrolidine hydrochloride (1.07 g, 5.8 mmol) was added. The reaction mixture was stirred for 24 h at 60° C. (TLC monitoring, CHCl3/MeOH, 9:1), diluted with water, and extracted with ethyl acetate. The extract was dried with Na2SO4 and evaporated. The residue was purified by column chromatography (silica gel, CHCl3/MeOH 99:1→90:10) to give 0.90 g (64%) of the product. 1H NMR (DMSO-d6): δ 1.41-1.49 (1H, m); 1.54-1.73 (3H, m); 1.76-1.85 (1H, m); 1.97-2.13 (3H, m); 2.14 (3H, s); 2.70 (6H, s); 2.86-2.93 (1H, m); 4.46-4.50 (2H, m); 7.72 (2H, d, J=8.8 Hz); 8.12 (2H, dd, J=8.8 Hz, J=1.6 Hz); 9.04 (2H, d, J=1.6 Hz). ELSD: 100%, ESI-MS: m/z 363 [M+H]+.

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried with Na2SO4
  3. customevaporated
  4. customThe residue was purified by column chromatography (silica gel, CHCl3/MeOH 99:1→90:10)

出典と根拠

ORDレコード
ord-1eaf6179f4c646b2846a6e37e0ea0c31
出典データセット
uspto-grants-2015_08
特許番号
US09108916B2

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