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

HRID 1773062노트

반응식

HRID 1773062 반응식
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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-9ab4d87f8c144fe9853452a1cf7693f0
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09252368B2

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