Potassium Carbonate → HCID 86669956, compound

HRID 2273500Notes

Reaction equation

HRID 2273500 reaction equation
[CH3:1][C:2]1([CH3:22])[CH:14]=[C:13]2[C:5](=[C:6]3[C:11](=[CH:12]2)[CH:10]=[CH:9][C:8]2[CH:15]=[CH:16][C:17](B(O)O)=[CH:18][C:7]3=2)[CH:4]=[CH:3]1.Br[C:24]1[CH:25]=[C:26]([C:31]2[N:36]=[C:35]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[N:34]=[C:33]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[N:32]=2)[CH:27]=[C:28](Br)[CH:29]=1.C([O-])([O-])=O.[K+].[K+].[N:55]1[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=1[C:61]1[CH:66]=[CH:65][C:64](B(O)O)=[CH:63][CH:62]=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>[CH3:1][C:2]1([CH3:22])[CH:14]=[C:13]2[C:5](=[C:6]3[C:11](=[CH:12]2)[CH:10]=[CH:9][C:8]2[CH:15]=[CH:16][C:17]([C:24]4[CH:25]=[C:26]([C:31]5[N:36]=[C:35]([C:37]6[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=6)[N:34]=[C:33]([C:43]6[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=6)[N:32]=5)[CH:27]=[C:28]([C:64]5[CH:63]=[CH:62][C:61]([C:56]6[CH:57]=[CH:58][CH:59]=[CH:60][N:55]=6)=[CH:66][CH:65]=5)[CH:29]=4)=[CH:18][C:7]3=2)[CH:4]=[CH:3]1

Participants

8

Reactant 4

HCID 11430Potassium Carbonate2×HCID 18980112B-(4-(2-Pyridinyl)phenyl)boronic acidHCID 583826152-(3,5-Dibromophenyl)-4,6-diphenyl-1,3,5-triazineHCID 866699579,9-Dimethyl-2-benzo(c)fluoreneboronic acid

Product 1

HCID 86669956HCID 86669956, compoundYield 38%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

In a stream of argon, 185 mg (0.644 mmol) of 9,9-dimethyl-2-benzo[c]fluoreneboronic acid, 300 mg (0.644 mmol) of 2-(3,5-dibromophenyl)-4,6-diphenyl-1,3,5-triazine and 7.44 mg (0.00644 mmol) of tetrakis(triphenylphosphine)palladium were suspended in a mixed solvent composed of 24 mL of toluene and 3 mL of ethanol, and the resultant suspension was heated to 50° C. To the suspension, 1.93 ml (1.93 mmol) of an aqueous 1M K2CO3 solution was gradually added dropwise, and the mixture was stirred for 3 hours. The resultant reaction mixture was heated to 80° C. and further stirred for 3 hours. The reaction mixture was cooled to room temperature, and then, 256 mg (1.29 mmol) of 4-(2-pyridyl)phenylboronic acid and 2.90 mL (2.90 mmol) of an aqueous 1M K2CO3 solution were added to the reaction mixture. The resultant mixture was heated to 80° C., and maintained at that temperature for 24 hours while being stirred. The obtained reaction mixture was cooled to room temperature, and 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 172 mg of the target 2-[5-(9,9-dimethylbenzo[c]fluoren-2-yl)-4′-(2-pyridyl)biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine as a white solid (yield: 38.0%).

Workup

  1. customThe resultant reaction mixture
  2. stirringfurther stirred for 3 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. temperaturemaintained at that temperature for 24 hours
  5. stirringwhile being stirred
  6. customThe obtained reaction mixture
  7. temperaturewas cooled to room temperature
  8. distillationdistilled under a reduced pressure
  9. customto remove all volatile materials
  10. additionMethanol was added to the concentrate
  11. filtrationthe thus-deposited solid was collected by filtration
  12. customThe obtained crude product
  13. customwas purified by silica gel chromatography
  14. additionmixed solvent as an eluent

Sources & evidence

ORD record
ord-2cd58b33124e4b08a9c9f8c5ff82f321
Source dataset
uspto-grants-2015_09
Patent number
US09120773B2

Reaction notes

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