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

HRID 626259ノート

反応式

HRID 626259 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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]+.

後処理

  1. temperatureunder reflux

出典と根拠

ORDレコード
ord-4840e4ee9156411299429d817afa72b6
出典データセット
uspto-grants-2016_04
特許番号
US09309211B2

反応ノート

読み込み中…