Potassium Carbonate → 7-(2-Cyanoethyl)-1-[3-[2-E-(7-chloroquinolin-2-yl)ethenyl]benzyl]-2,3-dihydroindole

HRID 54529Notes

Reaction equation

[C:1]([CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:13]=1[NH:12][CH2:11][CH2:10]2)#[N:2].[Cl:14][C:15]1[CH:24]=[C:23]2[C:18]([CH:19]=[CH:20][C:21](/[CH:25]=[CH:26]/[C:27]3[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=3)[CH2:30]Cl)=[N:22]2)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.C(OCC)(=O)C>[C:1]([CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:13]=1[N:12]([CH2:30][C:29]1[CH:32]=[CH:33][CH:34]=[C:27](/[CH:26]=[CH:25]/[C:21]3[CH:20]=[CH:19][C:18]4[C:23](=[CH:24][C:15]([Cl:14])=[CH:16][CH:17]=4)[N:22]=3)[CH:28]=1)[CH2:11][CH2:10]2)#[N:2]

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 7-(2-cyanoethyl)-2,3-dihydroindole (690 mg, 4.01 mmol), 3-[2-E-(7-chloroquinolin-2-yl)ethenyl]benzyl chloride (product of Example 3), 1.29 g, 4.10 mmol), and potassium carbonate (1.10 g, 7.97 mmol) in DMF (100 mL), was heated in an oil bath at 85° C. for 16 hours. The mixture was cooled and diluted with water and ethyl acetate. The organic solution was separated, washed once with water, once with saturated sodium chloride solution, then dried (over sodium sulfate), filtered, and concentrated in vacuo. Chromatography (silica gel, 70% hexane/30% ether) of the resulting residue provided 850 mg (47%) of the intermediate.

Workup

temperatureThe mixture was cooled
customThe organic solution was separated
washwashed once with water, once with saturated sodium chloride solution
dry with materialdried (over sodium sulfate)
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-91fd433367b04121bc9403d0a1de8b60
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05622969

Reaction notes

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