3-Pyridinecarboxaldehyde → 1-(4-Ethylpiperazin-1-yl)-3-[(3-pyridyl)hydroxymethyl]isoquinoline

HRID 1251264ノート

反応式

HRID 1251264 の反応式
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11](Br)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2].[Li]CCCC.[CH:25]([C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)=[O:26]>O1CCCC1.C(OCC)(=O)C>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]([CH:25]([C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)[OH:26])[N:10]=2)[CH2:5][CH2:4]1)[CH3:2]

参加物

6

反応物 3

HCID 103713-PyridinecarboxaldehydeHCID 225024471-(1-Ethylpiperazin-4-yl)-3-bromoisoquinolineHCID 178418339Butyllithium

生成物 1

HCID 225024871-(4-Ethylpiperazin-1-yl)-3-[(3-pyridyl)hydroxymethyl]isoquinoline収率 35.3%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 1-(4-ethylpiperazin-1-yl)-3-bromoisoquinoline (0.39 g) obtained in Example 28-2, in tetrahydrofuran (10 ml) was cooled to −78° C., followed by the dropwise addition of 2.5M n-BuLi (0.6 ml). Fifteen minutes later, a solution of 3-formylpyridine (0.2 g) in tetrahydrofuran (3 ml) was added dropwise thereto. The temperature of the reaction solution was gradually raised to room temperature. The reaction solution was diluted with ethyl acetate, washed with brine, water and an aqueous solution of saturated sodium chloride, and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system), to give the title compound (0.15 g) as a pale yellow oil.

後処理

  1. washwashed with brine, water
  2. dry with materialan aqueous solution of saturated sodium chloride, and dried over magnesium sulfate
  3. customThe solvent was evaporated
  4. customthe resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system)

出典と根拠

ORDレコード
ord-b7cd681e809648ffad9aa957dfdfb594
出典データセット
uspto-grants-2002_01
特許番号
US06340759B1

反応ノート

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