Azepane → 4-(1-(4-(2-(Azepan-1-yl)ethoxy)phenyl)-2-(2-chlorobenzofuran-5-yl)but-1-enyl)phenol

HRID 626256Notes

Reaction equation

HRID 626256 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[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>CO>[N:32]1([CH2:21][CH2:20][O:19][C:16]2[CH:15]=[CH:14][C:13]([C:12]([C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=3)=[C:11]([C:8]3[CH:9]=[CH:10][C:4]4[O:3][C:2]([Cl:1])=[CH:6][C:5]=4[CH:7]=3)[CH2:30][CH3:31])=[CH:18][CH:17]=2)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

4

Reactant 2

HCID 8119AzepaneHCID 1239950204-(2-(2-Chlorobenzofuran-5-yl)-1-(4-(2-chloroethoxy)phenyl)but-1-enyl)phenol

Product 1

HCID 726804804-(1-(4-(2-(Azepan-1-yl)ethoxy)phenyl)-2-(2-chlorobenzofuran-5-yl)but-1-enyl)phenolYield 48%

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 (220 mg, 1.0 eq, made by example 11, step D) was reacted with azepane (500 mg) in MeOH under reflux to give the desired product (105 mg, 48%, Z/E=1/1). 1H NMR (400 MHz, CDCl3) δ 7.22 (d, J=1.6 Hz, 1H), 7.19 (d, J=8.4 Hz, 1H), 7.14 (d, J=8.4 Hz, 1H), 7.07 (d, J=8.8 Hz, 1H), 6.97-7.01 (m, 1H), 6.87 (d, J=8.4 Hz, 1H), 6.84 (d, J=8.4 Hz, 1H), 6.75 (d, J=8.8 Hz, 1H), 6.76 (d, J=8.8 Hz, 1H), 6.50 (d, J=8.4 Hz, 1H), 6.45 (d, J=8.8 Hz, 1H), 6.43-6.44 (m, 1H), 4.46-4.48 (m, 1H), 4.25-4.27 (m, 1H), 3.00-3.71 (m, 6H), 2.44-2.51 (m, 2H), 1.73-2.00 (m, 8H), 0.91 (t, J=7.6 Hz, 3H); m/z=516[M+1]+.

Workup

  1. temperatureunder reflux

Sources & evidence

ORD record
ord-7b087cf64c694bf1ae6b00b9bd492c17
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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