Trimethylsilylacetylene → HCID 58319144, compound

HRID 2043005Notes

Reaction equation

HRID 2043005 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:10][CH:9]2[C:11]([O:13][CH3:14])=[O:12])=[CH:4][CH:3]=1.C(P(C(C)(C)C)C1N(C2C=CC=CC=2)C2C(C=1)=CC=CC=2)(C)(C)C.[CH3:39][Si:40]([C:43]#[CH:44])([CH3:42])[CH3:41]>[Cu]I.CN(C)CCN(C)C>[CH3:39][Si:40]([C:43]#[C:44][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:10][CH:9]2[C:11]([O:13][CH3:14])=[O:12])=[CH:4][CH:3]=1)([CH3:42])[CH3:41]

Participants

6

Reactant 3

HCID 66111TrimethylsilylacetyleneHCID 111751332-(di-tert-butylphosphino)-N-phenylindoleHCID 58319110HCID 58319110, compound

Product 1

HCID 58319144HCID 58319144, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8037N,N,N',N'-TetramethylethylenediamineSolvent

Procedure

The title compound was prepared from and according to the general procedure A dry Schlenk flask was charged with methyl 2-(4-iodophenyl)cyclopropanecarboxylate (1.66 g, 5.49 mmol), Na2[PdCl4] (18 mg, 0.06 mmol), 2-(di-tert-butylphosphino)-1-phenylindole (37 mg, 0.11 mmol), CuI (21 mg, 0.11 mmol), and tetramethylethylenediamine (10 mL). The mixture was evacuated and backfilled with Ar (3×), and heated to 70° C. before addition of trimethylsilylacetylene (1.4 mL, 10.8 mmol) through the septum and the temperature was elevated to 80° C. After consumption of the starting material indicated by HPLC, the reaction mixture was cooled to room temperature, quenched with water and extracted with EtOAc (3×). The combined extracts were washed with brine, dried over MgSO4 and concentrated under vacuum and a fraction of the residue was purified by flash chromatography to give 580 mg (40%) after purification by flash chromatography (SiO2, EtOAc:PE, 1:8): Rt: 14.56 min (HPLC method I).

Workup

  1. customThe mixture was evacuated
  2. customwas elevated to 80° C
  3. customAfter consumption of the starting material
  4. customquenched with water
  5. extractionextracted with EtOAc (3×)
  6. washThe combined extracts were washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated under vacuum
  9. customa fraction of the residue was purified by flash chromatography
  10. customto give 580 mg (40%)
  11. customafter purification by flash chromatography (SiO2, EtOAc:PE, 1:8)

Sources & evidence

ORD record
ord-52fcee44589d4cdaba9ff40d1901e760
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

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