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Quinoline → (Z)-tert-butyl 4-(1-(4-methoxybenzyl)-3-(2-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)vinyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

HRID 387551
ノート
印刷プレビュー

反応式

HRID 387551 の反応式
[CH3:1][O:2][C:3]1[CH:53]=[CH:52][C:6]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[C:15]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:16]([N:17]4[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]4)=[C:11]3[C:10]([C:36]#[C:37][C:38]3[CH:39]=[N:40][N:41]([CH2:43][C:44]4[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[CH:46][CH:45]=4)[CH:42]=3)=[N:9]2)=[CH:5][CH:4]=1.N1C2C(=CC=CC=2)C=CC=1>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].CO.C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[C:15]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:16]([N:17]4[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:27])[CH3:28])=[O:24])[CH2:21][CH2:22]4)=[C:11]3[C:10](/[CH:36]=[CH:37]\[C:38]3[CH:39]=[N:40][N:41]([CH2:43][C:44]4[CH:45]=[CH:46][C:47]([O:50][CH3:51])=[CH:48][CH:49]=4)[CH:42]=3)=[N:9]2)=[CH:52][CH:53]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 7047QuinolineHCID 68768812tert-butyl 4-(1-(4-methoxybenzyl)-3-((1-(4-methoxybenzyl)-1H-pyrazol-4-yl)ethynyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

生成物 1

HCID 68757876(Z)-tert-butyl 4-(1-(4-methoxybenzyl)-3-(2-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)vinyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate収率 74%

試薬・触媒・溶媒 3

HCID 131709914
Lindlars catalyst
触媒
HCID 241Benzene溶媒
HCID 887Methanol溶媒

実験手順

A solution of tert-butyl 4-(1-(4-methoxybenzyl)-3-((1-(4-methoxybenzyl)-1H-pyrazol-4-yl)ethynyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.12 g, 0.169 mmol), quinoline (0.011 g, 0.085 mmol) and Lindlar's Catalyst (0.18 g, 0.085 mmol) in MeOH (3 mL) and benzene (3 mL) was charged with 1 atmosphere H2 and stirred at room temperature for 6 hours. The catalyst was removed by filtration and washed with ethyl acetate. The filtrate was concentrated in vacuo, and the residue obtained was purified flash chromatography on silica gel (hexane:ethyl acetate=1:1) to give (Z)-tert-butyl 4-(1-(4-methoxybenzyl)-3-(2-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)vinyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.089 g, 74%) as a solid.

後処理

  1. customThe catalyst was removed by filtration
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue obtained
  5. customwas purified flash chromatography on silica gel (hexane:ethyl acetate=1:1)

出典と根拠

ORDレコード
ord-dc11442462d242cba76373bb79dd0c07
出典データセット
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08372842B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート