Sodium Bicarbonate → 7-Dibenzofuran-4-yl-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene

HRID 2275950Notes

Reaction equation

HRID 2275950 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH:9]=[C:8]3[C:15]([CH3:23])([CH3:22])[C:16]4[C:21]([C:7]3=[CH:6][C:5]2=1)=[CH:20][CH:19]=[CH:18][CH:17]=4.[CH:24]1[C:32]2[C:31]3[CH:33]=[CH:34][CH:35]=[CH:36][C:30]=3[O:29][C:28]=2[C:27](B(O)O)=[CH:26][CH:25]=1.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.C(O)C>[CH:24]1[C:32]2[C:31]3[CH:33]=[CH:34][CH:35]=[CH:36][C:30]=3[O:29][C:28]=2[C:27]([C:2]2[CH:3]=[C:4]3[C:12](=[CH:13][CH:14]=2)[NH:11][C:10]2[CH:9]=[C:8]4[C:15]([CH3:23])([CH3:22])[C:16]5[C:21]([C:7]4=[CH:6][C:5]3=2)=[CH:20][CH:19]=[CH:18][CH:17]=5)=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734328Dibenzofuran-4-boronic acidHCID 667977897-Bromo-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene

Product 1

HCID 667975987-Dibenzofuran-4-yl-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

32 g (90.6 mmol) of 7-bromo-12,12-dimethyl-10,12-dihydro-10-azaindeno-[2,1-b]fluorene, 19.9 g (94 mmol) of dibenzofuran-4-boronic acid and 164 ml of saturated NaHCO3 solution are suspended in 1640 ml of toluene and 164 ml of ethanol. 1.9 g (1.6 mmol) of Pd(PPh)3 are added to this suspension, and the reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is separated off, filtered through silica gel, washed three times with 200 ml of water and subsequently evaporated to dryness. The yield is 26.7 g (59 mmol), corresponding to 65% of theory.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 16 h
  3. temperatureAfter cooling
  4. customthe organic phase is separated off
  5. filtrationfiltered through silica gel
  6. washwashed three times with 200 ml of water
  7. customsubsequently evaporated to dryness

Sources & evidence

ORD record
ord-d3a0abd91cb5479699931c2148dfa21f
Source dataset
uspto-grants-2015_09
Patent number
US09126970B2

Reaction notes

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