Cesium carbonate → HCID 15555103, compound

HRID 2390892Notes

Reaction equation

HRID 2390892 reaction equation
Br[C:2]1[C:3]([CH2:12][O:13][CH2:14][B-](F)(F)F)=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[Na+].O1CCOCC1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.ClCCl.O>[CH2:14]1[C:2]2[CH:11]=[C:10]3[C:5](=[CH:4][C:3]=2[CH2:12][O:13]1)[CH:6]=[CH:7][CH:8]=[CH:9]3

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 131729969HCID 131729969, compound

Product 1

HCID 15555103HCID 15555103, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

To the mixture of sodium (((3-bromo-2-naphthyl)methoxy)methyl)trifluoroborate (30 mg, 0.088 mmol) synthesized in Example 6 and 1,4-dioxane (1.0 ml), water (0.15 ml), cesium carbonate (86 mg, 0.26 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (7.2 mg, 0.018 mmol), palladium(II) acetate (2.0 mg, 0.009 mmol) were added at room temperature, and the obtained reaction mixture was then stirred at 100° C. (an outer temperature) for 16 hours. The reaction mixture was cooled to room temperature, and then water and dichloromethane were added thereto, followed by filtration with Celite. The organic layer of the filtrate was separated and washed with saturated saline. The solvents were evaporated under reduced pressure from the organic layer, and then the obtained residue was purified with silica gel column chromatography (hexane:ethyl acetate=10:1), thereby obtaining the entitled compound (10 mg, 67%).

Workup

  1. additionwere added at room temperature
  2. customthe obtained reaction mixture
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationfollowed by filtration with Celite
  5. customThe organic layer of the filtrate was separated
  6. washwashed with saturated saline
  7. customThe solvents were evaporated under reduced pressure from the organic layer
  8. customthe obtained residue was purified with silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-2a105c7927bc46ff9ee7cfc72f8567a2
Source dataset
uspto-grants-2012_09
Patent number
US08273885B2

Reaction notes

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