Sodium Carbonate → HCID 66797678, compound

HRID 2275940Notes

Reaction equation

HRID 2275940 reaction equation
BrC1C=C([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)C=C(Br)N=1.[N:31]1[CH:36]=[CH:35][CH:34]=[C:33](B(O)O)[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>[CH3:28][C:21]1([CH3:29])[C:18]2=[CH:19][C:20]3[N:8]([C:34]4[CH:35]=[C:36]([C:33]5[CH:32]=[N:31][CH:36]=[CH:35][CH:34]=5)[N:31]=[C:32]([C:33]5[CH:32]=[N:31][CH:36]=[CH:35][CH:34]=5)[CH:33]=4)[C:9]4[C:14]([C:15]=3[CH:16]=[C:17]2[C:27]2[C:22]1=[CH:23][CH:24]=[CH:25][CH:26]=2)=[CH:13][CH:12]=[CH:11][CH:10]=4

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 86663412HCID 86663412, compound

Product 1

HCID 66797678HCID 66797678, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

20 g (38.6 mmol) of 10-(2,6-dibromopyridin-4-yl)-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene and 10.4 g of 3-pyridineboronic acid (84.9 mmol) are suspended in 400 ml of ethylene glycol dimethyl ether. 85 ml of a 2 M Na2CO3 solution are added to the reaction mixture. 2.23 g (1.93 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, recrystallised from toluene and finally sublimed in a high vacuum, the purity is 99.9%. Yield: 12 g, 60% 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-dc7bea95763a438396ecb1a650af6041
Source dataset
uspto-grants-2015_09
Patent number
US09126970B2

Reaction notes

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