Sodium Carbonate → HCID 67288842, compound

HRID 576461Notes

Reaction equation

HRID 576461 reaction equation
Br[C:2]1[CH:7]=[C:6]([N:8]2[C:27]3[C:15](=[CH:16][C:17]4[C:18]([CH3:29])([CH3:28])[C:19]5[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=5[C:25]=4[CH:26]=3)[C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:5]=[C:4](Br)[N:3]=1.[C:31]1(B(O)O)[CH:36]=[CH:35][CH:34]=[CH: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>[C:31]1([C:2]2[CH:7]=[C:6]([N:8]3[C:27]4[C:15](=[CH:16][C:17]5[C:18]([CH3:29])([CH3:28])[C:19]6[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=6[C:25]=5[CH:26]=4)[C:14]4[C:9]3=[CH:10][CH:11]=[CH:12][CH:13]=4)[CH:5]=[C:4]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[N:3]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 86664282HCID 86664282, compound

Product 1

HCID 67288842HCID 67288842, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

25 g (48 mmol) of 6-(2,6-dibromopyridin-4-yl)-12,12-dimethyl-6,12-dihydro-6-azaindeno[1,2-b]fluorene and 12.9 g of phenylboronic acid (106 mmol) are suspended in 300 ml of ethylene glycol dimethyl ether. 75 ml of a 2 M Na2CO3 solution are added to the reaction mixture. 2.8 g (2.4 mmol) of Pd(PPh3)4 are added to this suspension. The reaction mixture is heated under reflux for 12 h. After cooling, the solid which has precipitated out is filtered off with suction, washed with water and ethanol and dried. The residue is extracted with hot toluene, recrystallised from toluene and finally sublimed in a high vacuum, the purity is 99.9%. Yield: 18 g, 72% of theory.

Workup

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

Sources & evidence

ORD record
ord-c056cedac1c945e8a0bf8ac371efd2ea
Source dataset
uspto-grants-2015_05
Patent number
US09040172B2

Reaction notes

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