Water → HCID 67778666, compound

HRID 1026243Notes

Reaction equation

HRID 1026243 reaction equation
[H-].[Na+].Br[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH:12]2[CH2:14][CH2:13]2)[CH:7]=[CH:6][C:5]=1[CH2:15][CH:16]([C:18]1[CH:23]=[CH:22][C:21]([O:24][Si](C(C)C)(C(C)C)C(C)C)=[CH:20][N:19]=1)[OH:17].O>C1(C)C=CC=CC=1.[Cu]Cl>[CH:12]1([CH2:11][O:10][C:8]2[CH:7]=[CH:6][C:5]3[CH2:15][CH:16]([C:18]4[N:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=4)[O:17][C:4]=3[CH:9]=2)[CH2:14][CH2:13]1

Participants

6

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 67777123HCID 67777123, compound

Product 1

HCID 67778666HCID 67778666, compoundYield 55.1%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

Sodium hydride (27.7 mg) was added to a suspension of 2-[2-bromo-4-(cyclopropylmethoxy)phenyl]-1-(5-{[tris(1-methylethyl)silyl]oxy}pyridin-2-yl)ethanol (600 mg) and copper(I) chloride (5.71 mg) in toluene (10 mL) at room temperature. The reaction mixture was stirred at 120° C. for 3 hr, and allowed to cool to room temperature. Water was added to the mixture, and the mixture was extracted with ethyl acetate. The combined organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was dissolved in THF (10 mL), and a THF solution (1.0 M, 5.76 mL) of tetrabutylammonium fluoride was added thereto. The reaction mixture was stirred at room temperature for 30 min, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (180 mg).

Workup

  1. temperatureto cool to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. dissolutionThe residue was dissolved in THF (10 mL)
  7. additiona THF solution (1.0 M, 5.76 mL) of tetrabutylammonium fluoride was added
  8. stirringThe reaction mixture was stirred at room temperature for 30 min
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-08613bd4529644bb9816f85895ae9493
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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