6-Bromoquinoline → HCID 68083972, compound

HRID 2273486Notes

Reaction equation

HRID 2273486 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[CH2:12]([Li])[CH2:13][CH2:14][CH3:15].Br[C:18]1[CH:19]=[C:20]([C:25]2[N:30]=[C:29]([C:31]3[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=3)[CH:28]=[C:27]([C:38]3[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][CH:39]=3)[N:26]=2)[CH:21]=[C:22](Br)[CH:23]=1>O1CCCC1.CCCCCC.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>[N:8]1[C:9]2[C:4](=[CH:3][C:2]([C:18]3[CH:19]=[C:20]([C:25]4[N:30]=[C:29]([C:31]5[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=5)[CH:28]=[C:27]([C:38]5[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][CH:39]=5)[N:26]=4)[CH:21]=[C:22]([C:13]4[CH:14]=[C:15]5[C:9](=[CH:4][CH:12]=4)[N:8]=[CH:7][CH:6]=[CH:5]5)[CH:23]=3)=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 792436-BromoquinolineHCID 67983791HCID 67983791, compoundHCID 178418339Butyllithium

Product 1

HCID 68083972HCID 68083972, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

In a stream of argon, 0.34 g (1.62 mmol) of 6-bromoquinoline was dissolved in 7 mL of tetrahydrofuran, and then 1.03 mL of a solution of butyllithium 1.63 mmol in hexane was added dropwise at −78° C. The resultant mixture was stirred at −78° C. for 30 minutes, and then 0.41 g (1.63 mmol) of dichloro(tetramethylethylenediamine)zinc was added. The mixture was heated to room temperature and maintained at that temperature for 1 hour while being stirred. To the resultant mixture, 0.20 g (0.41 mmol) of 2-(3,5-dibromophenyl)-4,6-di-p-tolylpyrimidine, 19 mg (0.016 mmol) of tetrakis(triphenylphosphine)palladium and 3 mL of tetrahydrofuran were added, and the obtained suspension was heated under reflux for 17 hours. The reaction mixture was cooled to room temperature, and was then distilled under a reduced pressure to remove all volatile materials. The thus-deposited solid was collected by filtration. The thus-obtained crude product was purified by silica gel chromatography using a hexane/chloroform (1:1) mixed solvent as an eluent to give 0.16 g of the target 2-[3,5-di(6-quinolyl)phenyl-4,6-di-p-tolylpyrimidine as a white solid (yield: 65%).

Workup

  1. temperaturemaintained at that temperature for 1 hour
  2. temperaturethe obtained suspension was heated
  3. temperatureunder reflux for 17 hours
  4. temperatureThe reaction mixture was cooled to room temperature
  5. distillationwas then distilled under a reduced pressure
  6. customto remove all volatile materials
  7. filtrationThe thus-deposited solid was collected by filtration
  8. customThe thus-obtained crude product
  9. customwas purified by silica gel chromatography
  10. additionmixed solvent as an eluent

Sources & evidence

ORD record
ord-c6e8e82966a94a6aa67fa8fb227a5f52
Source dataset
uspto-grants-2015_09
Patent number
US09120773B2

Reaction notes

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