Propargyl bromide → 3-Methoxy-3-[3-(1-methyl-2-oxo-1,2-dihydroquinolin-6-ylmethoxy)phenyl]-1-(prop-2-ynyl)pyrrolidine

HRID 37552Notes

Reaction equation

[CH:1](N(C(C)C)CC)([CH3:3])[CH3:2].[CH3:10][O:11][C:12]1([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][C:25]3[CH:26]=[C:27]4[C:32](=[CH:33][CH:34]=3)[N:31]([CH3:35])[C:30](=[O:36])[CH:29]=[CH:28]4)[CH:18]=2)[CH2:16][CH2:15][NH:14][CH2:13]1.C(Br)C#C>>[CH3:10][O:11][C:12]1([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][C:25]3[CH:26]=[C:27]4[C:32](=[CH:33][CH:34]=3)[N:31]([CH3:35])[C:30](=[O:36])[CH:29]=[CH:28]4)[CH:18]=2)[CH2:16][CH2:15][N:14]([CH2:3][C:1]#[CH:2])[CH2:13]1

Participants

Reactant 3

HCID 7842Propargyl bromide

HCID 81531Diisopropylethylamine

HCID 57088300HCID 57088300, compound

Product 1

HCID 570816843-Methoxy-3-[3-(1-methyl-2-oxo-1,2-dihydroquinolin-6-ylmethoxy)phenyl]-1-(prop-2-ynyl)pyrrolidineYield 21%

Procedure

Using an analogous procedure to that described in Example 3 except that diisopropylethylamine was used in place of potassium carbonate, 3-methoxy-3-[3-(1-methyl-2-oxo-1,2-dihydroquinolin-6-ylmethoxy)phenyl]pyrrolidine was reacted with 2-propynyl bromide to give 3-methoxy-3-[3-(1-methyl-2-oxo-1,2-dihydroquinolin-6-ylmethoxy)phenyl]-1-(prop-2-ynyl)pyrrolidine as a gum in 21% yield.

Sources & evidence

ORD record: ord-7847c01625e040a0b1c90b096b774219
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05420298

Reaction notes

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