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

HRID 22820

Reaktionsgleichung

Reaktionsgleichung von HRID 22820
N1C=CC=CC=1.[C:7]([N:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][C:14]([S:20](Cl)(=[O:22])=[O:21])=[CH:15][CH:16]=2)[CH2:11]1)(=[O:9])[CH3:8].[NH:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26][CH2:25]1>ClCCCl>[N:24]1([S:20]([C:14]2[CH:13]=[C:12]3[C:17]([CH2:18][CH2:19][N:10]([C:7](=[O:9])[CH3:8])[CH2:11]3)=[CH:16][CH:15]=2)(=[O:22])=[O:21])[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26][CH2:25]1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 10328IndolineHCID 126069042-Acetyl-1,2,3,4-tetrahydroisoquinoline-7-sulfonyl chloride

Produkt 1

HCID 225920191-[7-(2,3-Dihydro-indole-1-sulfonyl)-3,4-dihydro-1H-isoquinolin-2-yl]-ethanoneAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

Pyridine (0.85 ml, 10.5 mmol) was added to a stirred solution of 2-acetyl-1,2,3,4-tetrahydroisoquinoline-7-sulfonyl chloride (0.96 g, 3.5 mmol) and 2,3-dihydro-1H-indole (0.42 g, 3.5 mmol) in 1,2-dichlorethane (40 ml) at room temperature. After 3 h, the solution was washed with water (40 ml), dried (MgSO4) and concentrated in vacuo to an oil. The oil was purified by column chromatography over silica gel eluting with a gradient of dichloromethane/methanol to afford the title compound (D5) as an oil (0.83 g, 67%), MS: m/z (MH+) 357.

Aufarbeitung

  1. washthe solution was washed with water (40 ml)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo to an oil
  4. customThe oil was purified by column chromatography over silica gel eluting with a gradient of dichloromethane/methanol

Quellen und Nachweise

ORD-Eintrag
ord-7cd696d750fc4bb188418451dc6d5112
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06849644B2

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