Pyrrolidine → 4-(2-(2-Chlorobenzofuran-5-yl)-1-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)but-1-enyl)phenol

HRID 626259Notes

Reaction equation

HRID 626259 reaction equation
[Cl:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([C:11]([CH2:30][CH3:31])=[C:12]([C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=3)[C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21]Cl)=[CH:15][CH:14]=3)=[CH:7][C:5]=2[CH:6]=1.[NH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1>CO>[Cl:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([C:11]([CH2:30][CH3:31])=[C:12]([C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=3)[C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][N:32]4[CH2:36][CH2:35][CH2:34][CH2:33]4)=[CH:15][CH:14]=3)=[CH:7][C:5]=2[CH:6]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 1239950204-(2-(2-Chlorobenzofuran-5-yl)-1-(4-(2-chloroethoxy)phenyl)but-1-enyl)phenol

Product 1

HCID 726804684-(2-(2-Chlorobenzofuran-5-yl)-1-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)but-1-enyl)phenolYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

According to the same procedure as example 1, step E described, 4-(2-(2-chlorobenzofuran-5-yl)-1-(4-(2-chloroethoxy)phenyl)but-1-enyl)phenol (70 mg, 1.0 eq, made by example 11, step D) was reacted with pyrrolidine (1 mL) in MeOH (3 mL) under reflux to give the desired product (51 mg, 68%, Z/E=1/2.6) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.24 (s, 1H), 7.20 (d, J=9.2 Hz, 1H), 7.09 & 7.06 (d, J=8.4 Hz, 2H), 7.00 (d, J=8.8 Hz, 1H), 6.78 & 6.72 (d, J=8.2 Hz, 2H), 6.68 (d, J=8.6 Hz, 2H), 6.46 & 6.45 (s, 1H), 6.41 & 6.27 (d, J=8.4 Hz, 2H), 4.10 & 3.89 (t, J=5.8 Hz, 2H), 2.94 & 2.83 (t, J=6.2 Hz, 2H), 2.68 & 2.61 (m, 4H), 2.49 (q, J=7.4 Hz, 2H), 1.84 & 1.81 (m, 4H), 0.91 (t, J=7.4 Hz, 3H); m/z=488[M+1]+.

Workup

  1. temperatureunder reflux

Sources & evidence

ORD record
ord-4840e4ee9156411299429d817afa72b6
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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