Indole → 1-[7-(Indole-1-sulfonyl)-3,4-dihydro-1H-isoquinolin-2-yl]-ethanone

HRID 22816

反応式

HRID 22816 の反応式
[OH-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:30]([N:33]1[CH2:42][CH2:41][C:40]2[C:35](=[CH:36][C:37]([S:43](Cl)(=[O:45])=[O:44])=[CH:38][CH:39]=2)[CH2:34]1)(=[O:32])[CH3:31]>O1CCCC1>[N:3]1([S:43]([C:37]2[CH:36]=[C:35]3[C:40]([CH2:41][CH2:42][N:33]([C:30](=[O:32])[CH3:31])[CH2:34]3)=[CH:39][CH:38]=2)(=[O:44])=[O:45])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1

参加物

6

反応物 4

HCID 798IndoleHCID 14798Sodium HydroxideHCID 2723671Tetrabutylammonium HydroxideHCID 126069042-Acetyl-1,2,3,4-tetrahydroisoquinoline-7-sulfonyl chloride

生成物 1

HCID 225920211-[7-(Indole-1-sulfonyl)-3,4-dihydro-1H-isoquinolin-2-yl]-ethanone収率 72%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A 50% solution of sodium hydroxide (100 ml) was added to a vigorously stirred solution of indole (5.8 g, 50 mmol) and tetrabutylammonium hydroxide (40% by weight solution, 2 ml, 3.1 mmol) in tetrahydrofuran (100 ml). After 5 minutes, a solution of 2-acetyl-1,2,3,4-tetrahydroisoquinoline-7-sulfonyl chloride (R. G. Pendleton et al., J. Pharmacol. Exp. Ther., 1979, 208, 24; U.S. Pat. No. 3,725,388 (1973)) (13.7 g, 50 mmol) in tetrahydrofuran (50 ml) was added over 10 minutes and the resulting mixture was vigorously stirred for a further 3 h. The mixture was then extracted with ethyl acetate (250 ml) and the extract dried (MgSO4), concentrated in vacuo and the residue purified by column chromatography over silica gel eluting with a dichloromethane/methanol gradient to give the title compound (D1) (12.8 g, 72%), NMR (CDCl3; rotamers observed)/ppm 2.12, 2.14 (3H, 2×s), 2.77-2.88 (2H, m), 3.60, 3.74 (3H, 2×t J=7 Hz), 4.59, 4.68 (2H, 2×s), 6.65-6.67 (1H, m), 7.16-7.34 (3H, m), 7.50-7.69 (4H, m), 7.94-7.99 (1H, m); MS: m/z (MH+) 355.

後処理

  1. extractionThe mixture was then extracted with ethyl acetate (250 ml)
  2. dry with materialthe extract dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customthe residue purified by column chromatography over silica gel eluting with a dichloromethane/methanol gradient

出典と根拠

ORDレコード
ord-14f05329adb54f16b989eb56a01c6cfa
出典データセット
uspto-grants-2005_02
特許番号
US06849644B2

関連ノート

読み込み中…