Hexane → HCID 67334338, compound

HRID 1671838Notes

Reaction equation

HRID 1671838 reaction equation
CCCCCC.C([Li])CCC.Br[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]3[N:30]=[C:29]([C:31]4[CH:36]=[CH:35][C:34]([C:37]([CH3:40])([CH3:39])[CH3:38])=[CH:33][CH:32]=4)[N:28]=[C:27]([C:41]4[CH:46]=[CH:45][C:44]([C:47]([CH3:50])([CH3:49])[CH3:48])=[CH:43][CH:42]=4)[N:26]=3)=[CH:21][CH:20]=2)=[CH:15][CH:14]=1.Br[C:52]1[CH:53]=[N:54][CH:55]=[CH:56][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.O1CCCC1>[C:47]([C:44]1[CH:45]=[CH:46][C:41]([C:27]2[N:28]=[C:29]([C:31]3[CH:36]=[CH:35][C:34]([C:37]([CH3:40])([CH3:39])[CH3:38])=[CH:33][CH:32]=3)[N:30]=[C:25]([C:22]3[CH:23]=[CH:24][C:19]([C:16]4[CH:17]=[CH:18][C:13]([C:52]5[CH:53]=[N:54][CH:55]=[CH:56][CH:57]=5)=[CH:14][CH:15]=4)=[CH:20][CH:21]=3)[N:26]=2)=[CH:42][CH:43]=1)([CH3:50])([CH3:49])[CH3:48]

Participants

7

Reactant 4

HCID 8058HexaneHCID 122863-BromopyridineHCID 67335182HCID 67335182, compoundHCID 178418339Butyllithium

Product 1

HCID 67334338HCID 67334338, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Under a stream of argon, 1.4 ml of a hexane solution containing 2.2 mmol of butyl lithium was slowly added to 50 ml of tetrahydrofuran cooled to −78° C. in which 1.15 g of 2-(4′-bromobiphenyl-4-yl)-4,6-bis(4-tert-butylphenyl)-1,3,5-triazine obtained in Reference Example 5 had been dissolved. After stirring at −78° C. for 15 minutes, 0.61 g of dichloro(tetramethylethylenediamine)zinc(II) was added thereto and stirred at −78° C. for 10 minutes and then at room temperature for 2 hours. A 10 ml portion of tetrahydrofuran prepared by dissolving 0.38 g of 3-bromopyridine and 0.09 g of tetrakis(triphenylphosphine)palladium(0) therein was added to this solution and stirred under heating reflux for 4 hours. The reaction solution was concentrated under a reduced pressure and the thus obtained solid was purified by a silica gel column chromatography (eluting solution hexane:chloroform=2:1 to chloroform) and an alumina gel column chromatography (eluting solution hexane:chloroform=2:1 to 3:2) and then recrystallized from dichloromethane-methanol to obtain a white solid of the intended 2,4-bis(4-tert-butylphenyl)-6-[4′-(3-pyridyl)biphenyl-4-yl]-1,3,5-triazine (0.71 g, yield 62%). Its melting point and glass transition temperature are shown in Table 4.

Workup

  1. customobtained in Reference Example 5
  2. dissolutionhad been dissolved
  3. stirringstirred at −78° C. for 10 minutes
  4. waitat room temperature for 2 hours
  5. additiontherein was added to this solution
  6. stirringstirred
  7. temperatureunder heating
  8. temperaturereflux for 4 hours
  9. concentrationThe reaction solution was concentrated under a reduced pressure
  10. customthe thus obtained solid was purified by a silica gel column chromatography (eluting solution hexane:chloroform=2:1 to chloroform)
  11. washan alumina gel column chromatography (eluting solution hexane:chloroform=2:1 to 3:2)
  12. customrecrystallized from dichloromethane-methanol

Sources & evidence

ORD record
ord-ecbd6b33e8c34e4dbd3dfe5dbc3412d8
Source dataset
uspto-grants-2011_08
Patent number
US07994316B2

Reaction notes

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