Water → HCID 67169847, compound

HRID 549599Notes

Reaction equation

HRID 549599 reaction equation
[CH2:1]([O:3][C:4](=[O:6])[CH3:5])[CH3:2].Br[C:8]1[CH:9]=[C:10]([S:21][C:22]2[CH:32]=[CH:31][C:25]([O:26]CC(O)=O)=[C:24]([CH3:33])[CH:23]=2)[CH:11]=[C:12]([O:14][CH2:15][CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:13]=1.[C:34]([C:36]1[CH:41]=[CH:40][C:39]([S:42]([CH3:45])(=[O:44])=[O:43])=[CH:38][CH:37]=1)#[CH:35].O.ClCCl>C(N(CC)CC)C.CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu](I)I>[CH2:1]([O:3][C:4](=[O:6])[CH2:5][O:26][C:25]1[CH:31]=[CH:32][C:22]([S:21][C:10]2[CH:9]=[C:8]([C:35]#[C:34][C:36]3[CH:37]=[CH:38][C:39]([S:42]([CH3:45])(=[O:44])=[O:43])=[CH:40][CH:41]=3)[CH:13]=[C:12]([O:14][CH2:15][CH:16]3[CH2:17][CH2:18][CH2:19][CH2:20]3)[CH:11]=2)=[CH:23][C:24]=1[CH3:33])[CH3:2]

Participants

9

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 220426121-Ethynyl-4-(methanesulfonyl)benzeneHCID 67170529HCID 67170529, compound

Product 1

HCID 67169847HCID 67169847, compound

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

[4-(3-Bromo-5-cyclopentylmethoxy-phenylsulfanyl)-2-methyl-phenoxy]-acetic acid ethyl acetate (0.24 g; 0.50 mmol), 1-Ethynyl-4-methanesulfonyl-benzene (0.271 g; 1.5 mmol), bis(triphenylphosphine)palladium (II) chloride (28.11 mg; 0.04 mmol) and copper iodide (5.7 mg; 0.03 mmol) were dissolved in a mixture of triethylamine (5 mL) and DMF (5 mL) under an atmosphere of nitrogen. The reaction mixture was reacted in a microwave oven at 120° C. for 1 h. Water and dichloromethane was added to the reaction mixture and the phases were separated and washed with water. The organic phase was dried and evaporated to dryness. The crude product was purified by prep. HPLC (Method A). Yield: 180 mg. HPLC-MS: m/z: 579.4 (M+H)+; Rt: 3.00 min.

Workup

  1. customThe reaction mixture was reacted in a microwave oven at 120° C. for 1 h
  2. customthe phases were separated
  3. washwashed with water
  4. customThe organic phase was dried
  5. customevaporated to dryness
  6. customThe crude product was purified by prep

Sources & evidence

ORD record
ord-659ceff73eae40269885193caa794776
Source dataset
uspto-grants-2011_05
Patent number
US07943669B2

Reaction notes

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