Cesium carbonate → 2-[4'-(1,10-Phenanthrolin-2-yl) biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine

HRID 1773062ノート

反応式

HRID 1773062 の反応式
Br[C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:11]=[C:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.CC1(C)C(C)(C)OB([C:34]2[CH:39]=[CH:38][C:37]([C:40]3[CH:53]=[CH:52][C:51]4[C:42](=[C:43]5[C:48](=[CH:49][CH:50]=4)[CH:47]=[CH:46][CH:45]=[N:44]5)[N:41]=3)=[CH:36][CH:35]=2)O1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:41]1[C:42]2[C:51](=[CH:50][CH:49]=[C:48]3[C:43]=2[N:44]=[CH:45][CH:46]=[CH:47]3)[CH:52]=[CH:53][C:40]=1[C:37]1[CH:38]=[CH:39][C:34]([C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([C:12]3[N:13]=[C:8]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=4)[N:9]=[C:10]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:11]=3)[CH:19]=2)=[CH:35][CH:36]=1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 583404452-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,10-phenanthrolineHCID 589433022-(3-Bromophenyl)-4,6-diphenyl-1,3,5-triazine

生成物 1

HCID 904016452-[4'-(1,10-Phenanthrolin-2-yl) biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 8028Tetrahydrofuran溶媒

実験手順

In a stream of argon, 1.20 g of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine, 1.30 g of 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,10-phenanthroline, 1.11 g of cesium carbonate, 14 mg of palladium acetate and 32 mg of triphenylphosphine were suspended in 140 mL of tetrahydrofuran. The suspension was heated under reflux for 19 hours. Then the reaction mixture was left to be cooled to room temperature, and distilled under a reduced pressure to remove low-boiling point ingredients. Methanol was added to the residue. The thus-deposited solid was collected by filtration, and purified by silica gel column chromatography using a methanol/chloroform (1:100 to 1:77) mixed solvent as a developing solvent to give 1.37 g of target 2-[4′-(1,10-phenanthrolin-2-yl) biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine as a white solid (yield, 79%).

後処理

  1. temperatureThe suspension was heated
  2. temperatureunder reflux for 19 hours
  3. waitThen the reaction mixture was left
  4. distillationdistilled under a reduced pressure
  5. customto remove low-boiling point ingredients
  6. additionMethanol was added to the residue
  7. filtrationThe thus-deposited solid was collected by filtration
  8. custompurified by silica gel column chromatography
  9. additionmixed solvent as a developing solvent
  10. customto give

出典と根拠

ORDレコード
ord-9ab4d87f8c144fe9853452a1cf7693f0
出典データセット
uspto-grants-2016_02
特許番号
US09252368B2

反応ノート

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