Phenylacetylene → HCID 76587260, compound

HRID 2358435Notes

Reaction equation

HRID 2358435 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][CH:8]([C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[C:12](I)[CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].[C:19]1([C:25]#[CH:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1.[Cu](I)I>[C:1]([O:5][C:6](=[O:18])[NH:7][CH:8]([C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([C:26]#[C:25][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 10821PhenylacetyleneHCID 68456838HCID 68456838, compound

Product 1

HCID 76587260HCID 76587260, compoundYield 97.5%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

[1-(4-Amino-3-iodophenyl)ethyl]carbamic acid tert-butyl ester (500 mg, 1.380 mmol, 1 eq.), dichloro(bistriphenylphosphine) palladium (48.4 mg, 0.069 mmol, 0.05 eq.) and copper iodide 13.1 mg (0.069 mmol, 0.05 eq.) were added in THF. After stirring for 30 min at room temperature, TEA (577.0 μl, 4.140 mmol, 3 eq) and phenylacetylene (197.0 μl, 1.794 mmol, 1.3 eq) were added into the reaction mixture. The reaction mixture was stirred overnight with reflux. A reaction solvent was removed in vacuo. The residue was purified with column chromatography (n-Hx:EA=5:1) to yield title compound (452.7 mg) as a yellow liquid.

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. temperaturewith reflux
  3. customA reaction solvent was removed in vacuo
  4. customThe residue was purified with column chromatography (n-Hx:EA=5:1)

Sources & evidence

ORD record
ord-cfe0e0034d244548b63738c15ac34b44
Source dataset
uspto-grants-2010_07
Patent number
US07763657B2

Reaction notes

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