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

HRID 1773060
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HRID 1773060 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: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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 167845
palladium(II) acetate
촉매
HCID 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-(4,4,5,5-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%).

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 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

출처 및 근거

ORD 기록
ord-eaf9331c2d51414f8a6e7c79b44aa520
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09252368B2

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