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

HRID 22820

Reaction equation

HRID 22820 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7cd696d750fc4bb188418451dc6d5112
Source dataset
uspto-grants-2005_02
Patent number
US06849644B2

Linked notes

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