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Cesium carbonate → 2-Bromo-6-{6-[2-(2-hydroxy-ethoxy)-1,1-dimethyl-ethyl]-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl}-benzaldehyde

HRID 2069824
ノート
印刷プレビュー

反応式

HRID 2069824 の反応式
[OH:1][CH2:2][C:3]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[N:11](CC1C=CC(OC)=CC=1)[CH2:10][CH2:9]2)([CH3:5])[CH3:4].Br[C:27]1[CH:34]=[CH:33][CH:32]=[C:31]([Br:35])[C:28]=1[CH:29]=[O:30].C(=O)([O-])[O-].[Cs+].[Cs+].[O:42]1CCO[CH2:44][CH2:43]1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[Br:35][C:31]1[CH:32]=[CH:33][CH:34]=[C:27]([N:11]2[CH2:10][CH2:9][C:8]3[C:13](=[CH:14][CH:15]=[C:6]([C:3]([CH3:4])([CH3:5])[CH2:2][O:1][CH2:44][CH2:43][OH:42])[CH:7]=3)[C:12]2=[O:16])[C:28]=1[CH:29]=[O:30]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 126486412,6-DibromobenzaldehydeHCID 671349876-(2-Hydroxy-1,1-dimethyl-ethyl)-2-(4-methoxy-benzyl)-3,4-dihydro-2H-isoquinolin-1-one

生成物 1

HCID 592165302-Bromo-6-{6-[2-(2-hydroxy-ethoxy)-1,1-dimethyl-ethyl]-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl}-benzaldehyde

試薬・触媒・溶媒 2

HCID 636044
1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)
触媒
HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒

反応条件

温度
100 °C

実験手順

Combined 0.131 g (0.5 mmol, 1 eq) 6-(2-Hydroxy-1,1-dimethyl-ethyl)-2-(4-methoxy-benzyl)-3,4-dihydro-2H-isoquinolin-1-one, 0.528 g 2,6-dibromobenzaldehyde (2 mmol, 4 eq), 6 mg Xantphos (0.01 mmol, 0.02 eq), 9 mg bis(dibenzylideneacetone)palladium (0.015 mmol, 0.03 eq), and 0.326 g Cesium Carbonate (1 mmol, 2.0 eq) in 5 ml dioxane, bubbled argon gas through the mixture for 1 minute, sealed the reaction vessel and heated at 100° C. for 13 hours, filtered through a sintered glass funnel while hot, concentrated and purified on a silica gel column eluting with 5% to 10% Methanol in CH2Cl2 to give 148 mg . Rotovaped, chromatographed (10% to 30% ea in hexanes) to give a solid, 325 mg 2-Bromo-6-{6-[2-(2-hydroxy-ethoxy)-1,1-dimethyl-ethyl]-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl}-benzaldehyde. MS (ESI) 446.0 (M+H)+.

後処理

  1. customsealed the reaction vessel
  2. filtrationfiltered through a sintered glass funnel while hot,
  3. concentrationconcentrated
  4. custompurified on a silica gel column
  5. washeluting with 5% to 10% Methanol in CH2Cl2
  6. customto give 148 mg
  7. customRotovaped, chromatographed (10% to 30% ea in hexanes)

出典と根拠

ORDレコード
ord-b1dfe1b21e0b42568a17d97eaaae91b5
出典データセット
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08299077B2

反応ノート

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