Triethylamine → 5-Biphenyl-4-ylethynyl-2-[(4-methoxy-benzenesulfonyl)-methyl-amino]-3-methyl-benzoic acid methyl ester

HRID 583390Notes

Reaction equation

HRID 583390 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[C:8](Br)[CH:7]=[C:6]([CH3:11])[C:5]=1[N:12]([S:14]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)(=[O:16])=[O:15])[CH3:13].C([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)#C.[CH2:40](N(CC)CC)[CH3:41]>CN(C=O)C.CCOCC.[Cu]I>[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[C:8]([C:40]#[C:41][C:37]2[CH:36]=[CH:35][C:34]([C:29]3[CH:28]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:39][CH:38]=2)[CH:7]=[C:6]([CH3:11])[C:5]=1[N:12]([S:14]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)(=[O:16])=[O:15])[CH3:13]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 127318612-Ethynyl-1,1'-biphenylHCID 699040625-Bromo-2-[(4-methoxy-benzenesulfonyl)-methyl-amino]-3-methyl-benzoic acid methyl ester

Product 1

HCID 700528885-Biphenyl-4-ylethynyl-2-[(4-methoxy-benzenesulfonyl)-methyl-amino]-3-methyl-benzoic acid methyl esterYield 63%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.0 g (2.336 mmol) of the product of Example 202 in 7.5 mL of DMF was added 0.50 g (2.804 mmol) of ethynyl biphenyl, 0.033 g (0.047 mmol) of bis triphenylphosphine palladium(II) dichloride 4.4 mg of copper(I) iodide and 7.5 mL of triethylamine. The reaction was heated to 80° for 5 h and then diluted with ether. the organics were washed with water, 5% HCl solution and sodium bicarbonate solution, dried over MgSO4, filtered and concentrated in vacuo. The residue was chromatographed on silica gel cluting with EtOAc/hexanes (1:3) to provide 0.777 g (63%) of the alkyne as a brown foam. Electrospray Mass Spec: 526.2 (M+H)+.

Workup

  1. temperatureThe reaction was heated to 80° for 5 h
  2. washthe organics were washed with water, 5% HCl solution and sodium bicarbonate solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel cluting with EtOAc/hexanes (1:3)

Sources & evidence

ORD record
ord-8d7a1204656b4ba9bfcd15e20560fabd
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

Loading…