Potassium Carbonate → 4,6-Diphenyl-2-[5-(9-phenanthryl)-4'-(2-pyridyl)biphenyl-3-yl]-pyrimidine

HRID 2273496ノート

反応式

HRID 2273496 の反応式
[CH:1]1[C:14]2[CH:13]=[C:12](B(O)O)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Br[C:19]1[CH:20]=[C:21]([C:26]2[N:31]=[C:30]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:29]=[C:28]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[N:27]=2)[CH:22]=[C:23](Br)[CH:24]=1.C([O-])([O-])=O.[K+].[K+].[N:50]1[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=1[C:56]1[CH:61]=[CH:60][C:59](B(O)O)=[CH:58][CH:57]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C.C1(C)C=CC=CC=1>[C:38]1([C:28]2[CH:29]=[C:30]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[N:31]=[C:26]([C:21]3[CH:20]=[C:19]([C:59]4[CH:58]=[CH:57][C:56]([C:51]5[CH:52]=[CH:53][CH:54]=[CH:55][N:50]=5)=[CH:61][CH:60]=4)[CH:24]=[C:23]([C:13]4[C:14]5[C:5]([C:6]6[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=6[CH:12]=4)=[CH:4][CH:3]=[CH:2][CH:1]=5)[CH:22]=3)[N:27]=2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

参加物

8

反応物 4

HCID 11430Potassium Carbonate2 回HCID 117757049-Phenanthracenylboronic acidHCID 18980112B-(4-(2-Pyridinyl)phenyl)boronic acidHCID 591334782-(3,5-Dibromophenyl)-4,6-diphenylpyrimidine

生成物 1

HCID 866699544,6-Diphenyl-2-[5-(9-phenanthryl)-4'-(2-pyridyl)biphenyl-3-yl]-pyrimidine収率 62%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒

実験手順

In a stream of argon, 0.714 g (3.22 mmol) of 9-phenanthreneboronic acid, 1.50 g (3.22 mmol) of 2-(3,5-dibromophenyl)-4,6-diphenylpyrimidine and 37.2 mg (0.0322 mmol) of tetrakis(triphenylphosphine)palladium were suspended in a mixed solvent composed of 120 mL of toluene and 15 mL of ethanol, and the resultant suspension was heated to 50° C. To the suspension, 9.66 mL (9.66 mmol) of an aqueous 1M K2CO3 solution was gradually added dropwise, and the mixture was stirred for 18 hours. Then the mixture was cooled to room temperature, and 0.961 g (4.83 mmol) of 4-(2-pyridyl)phenylboronic acid and 9.66 mL (9.66 mmol) of an aqueous 1M K2CO3 solution were added. Then the mixture was heated to 60° C. and maintained at that temperature for 4 hours while being stirred. Then the reaction mixture was cooled to room temperature, and was then distilled under a reduced pressure to remove all volatile materials. Methanol was added to the concentrate, and the thus-deposited solid was collected by filtration. The obtained crude product was purified by silica gel chromatography using a hexane/chloroform (1:2) mixed solvent as an eluent to give 1.28 g of the target 4,6-diphenyl-2-[5-(9-phenanthryl)-4′-(2-pyridyl)biphenyl-3-yl]-pyrimidine as a white solid (yield: 62%).

後処理

  1. temperatureThen the mixture was heated to 60° C.
  2. temperaturemaintained at that temperature for 4 hours
  3. stirringwhile being stirred
  4. temperatureThen the reaction mixture was cooled to room temperature
  5. distillationwas then distilled under a reduced pressure
  6. customto remove all volatile materials
  7. additionMethanol was added to the concentrate
  8. filtrationthe thus-deposited solid was collected by filtration
  9. customThe obtained crude product
  10. customwas purified by silica gel chromatography
  11. additionmixed solvent as an eluent

出典と根拠

ORDレコード
ord-d2a3b7a496db4c61831c5eb7021dc28b
出典データセット
uspto-grants-2015_09
特許番号
US09120773B2

反応ノート

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