Cesium carbonate → 1-Methyl-5-(pyridin-4-yl)-3,4-dihydroisoquinoline

HRID 532869ノート

反応式

HRID 532869 の反応式
I[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]=[C:7]2[CH3:12].[N:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:12][C:7]1[C:8]2[C:3](=[C:2]([C:16]3[CH:17]=[CH:18][N:13]=[CH:14][CH:15]=3)[CH:11]=[CH:10][CH:9]=2)[CH2:4][CH2:5][N:6]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 867113155-Iodo-1-methyl-3,4-dihydroisoquinoline

生成物 1

HCID 867113191-Methyl-5-(pyridin-4-yl)-3,4-dihydroisoquinoline収率 73.8%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 312751,4-Dioxane溶媒

実験手順

A mixture of 5-iodo-1-methyl-3,4-dihydroisoquinoline (3.0 g, 11.1 mmol), pyridin-4-ylboronic acid (2.04 g, 16.6 mmol), Pd(PPh3)2Cl2 (3.88 g, 5.53 mmol) and Cs2CO3 (10.8 g, 33.2 mmol) in 1,4-dioxane (45 mL) was heated to reflux for 24 h. The mixture was allowed to cool to RT, and then filtered. The filter cake was washed with AcOEt, and the filtrate was then concentrated in vacuo. The crude product was purified by flash chromatography (SiO2, DCM to DCM/MeOH 9:1) to afford the title compound (1.82 g) as a grey solid. UPLC-MS: MS 223.0 (M+H+); UPLC rt 0.38 min.

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 24 h
  3. filtrationfiltered
  4. washThe filter cake was washed with AcOEt
  5. concentrationthe filtrate was then concentrated in vacuo
  6. customThe crude product was purified by flash chromatography (SiO2, DCM to DCM/MeOH 9:1)

出典と根拠

ORDレコード
ord-e5f361ea3c594e97ad77ab86cdcfc7b0
出典データセット
uspto-grants-2014_10
特許番号
US08853203B2

反応ノート

読み込み中…