Triethylamine → HCID 68278456, compound

HRID 1423272Notes

Reaction equation

HRID 1423272 reaction equation
C(N(CC)CC)C.[CH3:8][Si:9]([C:12]#[CH:13])([CH3:11])[CH3:10].Cl[C:15]1[O:16][C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]=1>ClC(Cl)C.ClCCl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:8][Si:9]([C:12]#[C:13][C:15]1[O:16][C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]=1)([CH3:11])[CH3:10]

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 119862-ChlorobenzoxazoleHCID 66111Trimethylsilylacetylene

Product 1

HCID 68278456HCID 68278456, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of bis(triphenylphosphine)palladium(II) chloride (0.229 g, 0.326 mmol), triethylamine (1.815 mL, 13.02 mmol), copper(I) iodide (0.124 g, 0.651 mmol), trimethylsilylacetylene (29A, 1.645 mL, 11.72 mmol) and compound 28A (1.0 g, 6.51 mmol) in dichloroethane (10 mL) under an inert atmosphere was heated at 80° C. overnight. After the reaction was complete, the mixture was cooled, diluted with dichloromethane (10 mL), washed with aq. NaHCO3, dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with 0-5% EtOAc/hexanes to give a mixture of Compound 29B (575 mg) and Compound 29C (200 mg).

Workup

  1. temperaturethe mixture was cooled
  2. washwashed with aq. NaHCO3
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel eluting with 0-5% EtOAc/hexanes
  7. customto give

Sources & evidence

ORD record
ord-165049813bab4a1cacc2175dfd1d5940
Source dataset
uspto-grants-2015_01
Patent number
US08927559B2

Reaction notes

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