2-(Dimethylamino)ethanol → (Z)-4-(1-(6-(2-(dimethylamino)ethoxy)pyridin-3-yl)-2-phenylbut-1-enyl)phenol

HRID 626097Notes

Reaction equation

HRID 626097 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][OH:5].Cl[C:8]1[N:13]=[CH:12][C:11](/[C:14](/[C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)=[C:15](\[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)/[CH2:16][CH3:17])=[CH:10][CH:9]=1>>[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][O:5][C:8]1[N:13]=[CH:12][C:11](/[C:14](/[C:24]2[CH:25]=[CH:26][C:27]([OH:30])=[CH:28][CH:29]=2)=[C:15](\[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)/[CH2:16][CH3:17])=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 79022-(Dimethylamino)ethanolHCID 71617026(Z)-4-(1-(6-chloropyridin-3-yl)-2-phenylbut-1-enyl)phenol

Product 1

HCID 71617145(Z)-4-(1-(6-(2-(dimethylamino)ethoxy)pyridin-3-yl)-2-phenylbut-1-enyl)phenolYield 75%

Procedure

Following the same procedure as described in example 3, 2-(dimethylamino)ethanol (798 mg, 10 eq) and (Z)-4-(1-(6-chloropyridin-3-yl)-2-phenylbut-1-enyl)phenol (300 mg, 1 eq, prepared from example 1) were reacted to get the desired product (260 mg, 75% yield). 1H NMR (400 MHz, CDCl3) δ 7.54 (s, 1H), 7.14-7.20 (m, 2H), 7.01-7.09 (m, 5H), 6.93 (d, J=8.0 Hz, 1H), 6.78 (d, J=8.0 Hz, 2H), 5.84 (d, J=8.8 Hz, 1H), 4.22 (t, J=5.2 Hz, 2H), 2.70 (t, J=5.2 Hz, 2H), 2.50 (q, J=7.2 Hz, 2H), 2.35 (s, 6H), 0.91 (t, J=7.6 Hz, 3H); m/z=389 [M+1]+.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-7418d3e2996d4b748cf5d7ef985c9970
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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