Sodium Carbonate → HCID 66798064, compound

HRID 2275941Notes

Reaction equation

HRID 2275941 reaction equation
Br[C:2]1[CH:7]=[C:6]([N:8]2[C:20]3[CH:19]=[C:18]4[C:21]([CH3:29])([CH3:28])[C:22]5[C:27]([C:17]4=[CH:16][C:15]=3[C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][CH:13]=3)=[CH:26][CH:25]=[CH:24][CH:23]=5)[CH:5]=[C:4](Br)[N:3]=1.[N:31]1[CH:36]=[C:35](B(O)O)[CH:34]=[N:33][CH:32]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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:31]1[CH:36]=[C:35]([C:2]2[CH:7]=[C:6]([N:8]3[C:20]4[CH:19]=[C:18]5[C:21]([CH3:29])([CH3:28])[C:22]6[C:27]([C:17]5=[CH:16][C:15]=4[C:14]4[C:9]3=[CH:10][CH:11]=[CH:12][CH:13]=4)=[CH:26][CH:25]=[CH:24][CH:23]=6)[CH:5]=[C:4]([C:35]3[CH:36]=[N:31][CH:32]=[N:33][CH:34]=3)[N:3]=2)[CH:34]=[N:33][CH:32]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 86663412HCID 86663412, compound

Product 1

HCID 66798064HCID 66798064, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

15 g (29 mmol) of 10-(2,6-dibromopyridin-4-yl)-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene and 7.9 g of 5-pyrimidineboronic acid (63.7 mmol) are suspended in 300 ml of ethylene glycol dimethyl ether. 65 ml of a 2 M Na2CO3 solution are added to the reaction mixture. 1.67 g (1.45 mmol) of Pd(PPh3)4 are added to this suspension. The reaction mixture is heated under reflux for 12 h. After cooling, the precipitated solid is filtered off with suction, washed with water and ethanol and dried. The residue is extracted with hot toluene and recrystallised from toluene and finally sublimed in a high vacuum, the purity is 99.9%. Yield: 8.5 g, 57% of theory.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 12 h
  3. temperatureAfter cooling
  4. filtrationthe precipitated solid is filtered off with suction
  5. washwashed with water and ethanol
  6. customdried
  7. extractionThe residue is extracted with hot toluene
  8. customrecrystallised from toluene

Sources & evidence

ORD record
ord-95c5e7c40f1d46bca7ef8f5b1ef1b87e
Source dataset
uspto-grants-2015_09
Patent number
US09126970B2

Reaction notes

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