Butylamine → HCID 86241403, compound

HRID 2076682Notes

Reaction equation

HRID 2076682 reaction equation
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].C(N)CCC.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])=[C:15](I)[CH:14]=1>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Cu](I)I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])=[C:17]([C:6]#[C:5][Si:2]([CH3:4])([CH3:3])[CH3:1])[CH:18]=1

Participants

8

Reactant 3

HCID 8007ButylamineHCID 66111TrimethylsilylacetyleneHCID 86241402Methyl 4-bromo-2-iodobenzeneacetate

Product 1

HCID 86241403HCID 86241403, compoundYield 118.1%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 83717Copper iodideCatalystHCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Trimethylsilylacetylene (0.319 ml, 2.25 mmol), palladium acetate (12 mg, 56.3 μmol), triphenylphosphine (30 mg, 0.113 mmol), n-butylamine (0.334 ml, 3.38 mmol) and copper iodide (43 mg, 0.225 mmol) were added to a solution of methyl (4-bromo-2-iodophenyl)acetate (400 mg, 1.13 mmol) obtained in Example (85-1) in tetrahydrofuran (6 ml), and the mixture was stirred at room temperature for 3 hours. The solvent was removed under reduced pressure and the obtained residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=15/1) to give crude methyl (4-bromo-2-trimethylsilanylethynylphenyl)acetate (434 mg).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=15/1)

Sources & evidence

ORD record
ord-12f5cc443ff341ee8909462349da54b9
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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