Sodium Carbonate → HCID 118112466, compound

HRID 924547Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.C([O-])([O-])=O.[Na+].[Na+].[C:21]1([CH3:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH2:28](O)[CH3:29].O>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:21]1([C:27]2[C:28]3[C:29](=[CH:4][CH:3]=[CH:2][CH:14]=3)[C:13]([C:2]3[CH:3]=[CH:4][C:5]4[NH:6][C:7]5[C:12]([C:13]=4[CH:14]=3)=[CH:11][CH:10]=[CH:9][CH:8]=5)=[C:12]3[C:11]=2[CH:10]=[CH:9][CH:8]=[CH:7]3)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 120 °C

Procedure

3-bromocarbazole (2.54 g, 10.320 mmol), 9-phenyl-boronic acid (3.69 g, 12.384 mmol), Na2CO3 (2.2 g, 20.64 mmol), Pd(PPh3)4 (1.19 g, 1.032 mmol) were put in a 250 mL two-neck flask and dissolved in toluene/ethanol/H2O. The solution was refluxed and stirred at 120° C. for 12 hours. After completion of the reaction, the solution was extracted with methylenechloride/H2O and distilled under reduced pressure to remove the solvent. The resultant was columned with a solution of n-hexane and methylenechloride (4:1) and was re-crystallized in a solution of methylene chloride and petroleum ether such that the white solid compound was obtained, (2.60 g, yield: 60%).

Workup

temperatureThe solution was refluxed
customAfter completion of the reaction
extractionthe solution was extracted with methylenechloride/H2O
distillationdistilled under reduced pressure
customto remove the solvent
customwas re-crystallized in a solution of methylene chloride and petroleum ether such that the white solid compound
customwas obtained

Sources & evidence

ORD record: ord-cc1d3bd3dc5141688d5e291d71f5e884
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09281482B2

Reaction notes

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