1-Pyrrolidineethanol → (Z)-4-(2-phenyl-1-(6-(2-(pyrrolidin-1-yl)ethoxy)pyridin-3-yl)but-1-enyl)phenol

HRID 626099Notes

Reaction equation

[N:1]1([CH2:6][CH2:7][OH:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:10]1[N:15]=[CH:14][C:13](/[C:16](/[C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)=[C:17](\[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)/[CH2:18][CH3:19])=[CH:12][CH:11]=1>>[C:20]1(/[C:17](/[CH2:18][CH3:19])=[C:16](/[C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)\[C:13]2[CH:14]=[N:15][C:10]([O:8][CH2:7][CH2:6][N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:11][CH:12]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

Reactant 2

HCID 762881-Pyrrolidineethanol

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

Product 1

HCID 71617148(Z)-4-(2-phenyl-1-(6-(2-(pyrrolidin-1-yl)ethoxy)pyridin-3-yl)but-1-enyl)phenolYield 113.4%

Procedure

Following the same procedure as described in example 3, 2-(pyrrolidin-1-yl)ethanol (343 mg, 10 eq) and (Z)-4-(1-(6-chloropyridin-3-yl)-2-phenylbut-1-enyl)phenol (100 mg, 1 eq, prepared from example 1) were used as starting material to get the desired product (140 mg, 95%). 1H NMR (400 MHz, CDCl3) δ 7.53 (s, 1H), 7.15-7.20 (m, 2H), 7.01-7.13 (m, 6H), 6.92 (d, J=8.0 Hz, 1H), 6.76 (d, J=8.4 Hz, 2H), 5.68 (brs, 1H), 4.26 (bs, 2H), 2.91 (brs, 2H), 2.72 (brs, 4H), 2.50 (q, J=7.2 Hz, 2H), 1.89 (brs, 4H), 0.91 (t, J=7.6 Hz, 3H); m/z=415 [M+1]+.

Sources & evidence

ORD record: ord-0c05297584554c99ab4710878a597140
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309211B2

Reaction notes

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