Cesium carbonate → HCID 86657858, compound

HRID 1257561Notes

Reaction equation

HRID 1257561 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:20][C:21]1[C:22](Br)=[C:23]2[C:27](=[CH:28][CH:29]=1)[CH2:26][CH:25]=[CH:24]2>C1(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)C=CC=CC=1.COCCOC>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:22]1[C:21]([CH3:20])=[CH:29][CH:28]=[C:27]2[C:23]=1[CH:24]=[CH:25][CH2:26]2

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2734375(Naphthalen-2-yl)boronic acidHCID 58444066HCID 58444066, compound

Product 1

HCID 86657858HCID 86657858, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 178420554HCID 178420554, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To mixed solution of 2-naphthylboronic acid (5 g, 29 mmol) and DME (100 mL), aqueous solution (30 mL) of cesium carbonate (12 g, 36.8 mmol)(30 mL) and 5-methyl-4-bromoindene (4.3 g, 21 mmol), tetrakis(triphenylphosphino)palladium (0.9 g) were added, and heated under reflux. After 16 hours, reaction solution was poured into 1N HCl-ice water to separate organic layer after stirring. Organic layer was washed with saturated solution of sodium chloride after filtering through Celite, and dried over magnesium sulfate, and solvent was distilled off under reduced pressure. The obtained crude product was purified by column chromatography (Silica-gel: produced by Kanto Chemical Co., Inc., hexane) to obtain the desired 4-(2-naphthyl)-5-methylindene (3.9 g, yield: 74%).

Workup

  1. additionwere added
  2. temperatureheated
  3. temperatureunder reflux
  4. customreaction solution
  5. customto separate organic layer
  6. washOrganic layer was washed with saturated solution of sodium chloride
  7. filtrationafter filtering through Celite
  8. dry with materialdried over magnesium sulfate, and solvent
  9. distillationwas distilled off under reduced pressure
  10. customThe obtained crude product
  11. customwas purified by column chromatography (Silica-gel: produced by Kanto Chemical Co., Inc., hexane)

Sources & evidence

ORD record
ord-2fd3eb1ec7bc418cbe2aaf31d2e0e766
Source dataset
uspto-grants-2013_06
Patent number
US08461365B2

Reaction notes

Loading…