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Cesium carbonate → 4,6-Diphenyl-2-[3-(1,10-phenanthrolin-2-yl)phenyl]-1,3,5-triazine

HRID 1773060
ノート
印刷プレビュー

反応式

HRID 1773060 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:47]=[CH:46][C:45]3[C:36](=[C:37]4[C:42](=[CH:43][CH:44]=3)[CH:41]=[CH:40][CH:39]=[N:38]4)[N: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>[C:14]1([C:12]2[N:11]=[C:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:9]=[C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([C:39]4[CH:40]=[CH:41][C:42]5[C:37](=[C:36]6[C:45](=[CH:44][CH:43]=5)[CH:46]=[CH:47][CH:34]=[N:35]6)[N:38]=4)[CH:3]=3)[N:13]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1
参加物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 11776TriphenylphosphineHCID 589433022-(3-Bromophenyl)-4,6-diphenyl-1,3,5-triazineHCID 904015072-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,10-phenanthroline

生成物 1

HCID 904015744,6-Diphenyl-2-[3-(1,10-phenanthrolin-2-yl)phenyl]-1,3,5-triazine

試薬・触媒・溶媒 2

HCID 167845
palladium(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-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-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, and the deposited solid was collected by filtration. The thus-obtained crude product was 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 4,6-diphenyl-2-[3-(1,10-phenanthrolin-2-yl)phenyl]-1,3,5-triazine as a white solid (yield, 91%).

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 deposited solid was collected by filtration
  8. customThe thus-obtained crude product
  9. customwas purified by silica gel column chromatography
  10. additionmixed solvent as a developing solvent
  11. customto give

出典と根拠

ORDレコード
ord-eaf9331c2d51414f8a6e7c79b44aa520
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09252368B2

反応ノート

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