1-(4-Iodophenethyl)pyrrolidine → 3-[4-(2-Pyrrolidin-1-ylethyl)phenyl]propynoic acid-(4'-chlorobiphenyl-4-yl)amide

HRID 735032Notes

Reaction equation

HRID 735032 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:18])[C:16]#[CH:17])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.I[C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][N:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)=[CH:22][CH:21]=1>ClCCl.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:18])[C:16]#[C:17][C:20]3[CH:21]=[CH:22][C:23]([CH2:26][CH2:27][N:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)=[CH:24][CH:25]=3)=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 688158361-(4-Iodophenethyl)pyrrolidineHCID 86060771Propynoic acid-(4'-chlorobiphenyl-4-yl)amide

Product 1

HCID 578457903-[4-(2-Pyrrolidin-1-ylethyl)phenyl]propynoic acid-(4'-chlorobiphenyl-4-yl)amide

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 2.1.e. from propynoic acid-(4′-chlorobiphenyl-4-yl)amide and 1-[2-(4-iodophenyl)ethyl]pyrrolidine. Yield: 70 mg (32.8% of theory); melting point: 217-218 C; C27H25ClN2O (M=428.96); calc.: molecular ion peak (M+H)+: 429/431; found: molecular ion peak (M+H)+: 429/431; Rf value: 0.3 (silica gel, dichloromethane/methanol (10:1)).

Workup

  1. customPrepared analogously to Example 2.1.e

Sources & evidence

ORD record
ord-275f04bc74b741d6b1da0afa9367f83a
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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