Cesium carbonate → HCID 20748610, compound

HRID 1361420Notes

Reaction equation

HRID 1361420 reaction equation
Cl.Cl[CH2:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:5]=1.[C:20]([O-:23])([O-])=O.[Cs+].[Cs+].[C:26]([O-:29])(O)=O.[Na+]>CN(C=O)C>[C:14]1([C:6]2[CH:5]=[C:4]([CH2:3][O:29][C:26]3[CH:12]=[CH:13][C:4]([CH2:20][OH:23])=[CH:5][CH:6]=3)[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 23001450HCID 23001450, compound

Product 1

HCID 20748610HCID 20748610, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Compound C1 (2.14 g, 17.23 mmol), 4-chloromethyl-2-phenyl-quinoline HCl (5.0 g, 17.23 mmol), Cs2CO3 (11.8 g, 36.2 mmol), and dry DMF (60 mL) was stirred at room temperature for 20 hours. A saturated aqueous NaHCO3 solution was added and the aqueous phase was extracted with EtOAc (300 mL). The organic phase was washed with water (100 mL) and brine (100 mL), dried over Na2SO4, filtered, concentrated by rotary evaporator, and dried under vacuum overnight to give [4-(2-phenyl-quinolin-4-ylmethoxy)-phenyl]-methanol (5.81 g, 99%). [4-(2-Phenyl-quinolin-4-ylmethoxy)-phenyl]-methanol (4.0 g, 11.73 mmol) was dissolved in dry CH2Cl2 (60 mL) and was cooled to 0° C. before PBr3 (1.1 mL, 11.73 mmol, in 5 mL CH2Cl2) was added. The solution was stirred overnight at room temperature. The solution was poured into a cold aqueous NaHCO3 solution (250 mL) with stirring. The aqueous phase was extracted with EtOAc (150 mL) four times. The organic phase was washed with brine (50 mL), dried over Na2SO4, filtered, and concentrated by rotary evaporator to give compound C2 (4.3 g, 91%).

Workup

  1. extractionthe aqueous phase was extracted with EtOAc (300 mL)
  2. washThe organic phase was washed with water (100 mL) and brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporator
  6. customdried under vacuum overnight

Sources & evidence

ORD record
ord-6281824061214037a3725de9085683a0
Source dataset
uspto-grants-2011_02
Patent number
US07879997B2

Reaction notes

Loading…