Potassium Carbonate → HCID 77230740, compound

HRID 1628370Notes

Reaction equation

HRID 1628370 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[NH:5][C:4]=2[CH:3]=1.[CH:15]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)=[O:16].C(=O)([O-])[O-].[K+].[K+]>>[CH:3]1[C:4]2[NH:5][C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:12]=2[CH:13]=[CH:14][C:2]=1[C:20]1[CH:21]=[CH:22][C:17]([CH:15]=[O:16])=[CH:18][CH:19]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 127170892-Bromo-9H-carbazole

Product 1

HCID 77230740HCID 77230740, compoundYield 53%

Procedure

10.0 g of 2-bromo-9H-carbazole (4.06 10−2 mol), 9.22 g of 4-formylphenylboronic acid (6.15 10−2 mol), 0.63 g of tetrakistriphenylpalladium (5.5 10−4 mol), 42.0 g of potassium carbonate (3 10−1 mol) are initially introduced. After flushing through 300 ml of water with argon, 400 ml of THF is added. The reaction mixture is stirred under reflux for 2 days. After filtration through Celite, the organic phase is separated, dried over Na2CO4, and the aqueous phase is washed 2× with CH2Cl2 and dried over Na2SO4. Column chromatography with toluene as eluent give 2.0 g (53%) of clean product.

Workup

  1. customAfter flushing through 300 ml of water with argon, 400 ml of THF
  2. additionis added
  3. temperatureunder reflux for 2 days
  4. filtrationAfter filtration through Celite
  5. customthe organic phase is separated
  6. dry with materialdried over Na2CO4
  7. washthe aqueous phase is washed 2× with CH2Cl2
  8. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-fc90d3b6e91a47c1afa0ca388281a409
Source dataset
uspto-grants-2014_07
Patent number
US08786181B2

Reaction notes

Loading…