Water → HCID 67170987, compound

HRID 1969240Notes

Reaction equation

HRID 1969240 reaction equation
[CH2:1]([O:3][C:4](=[O:6])[CH3:5])[CH3:2].Br[C:8]1[CH:9]=[C:10]([S:22][C:23]2[CH:33]=[CH:32][C:26]([O:27]CC(O)=O)=[C:25]([CH3:34])[CH:24]=2)[CH:11]=[C:12]([O:14][CH2:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:13]=1.[C:35]([C:37]1[CH:42]=[CH:41][C:40]([S:43]([CH3:46])(=[O:45])=[O:44])=[CH:39][CH:38]=1)#[CH:36].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:27][C:26]1[CH:32]=[CH:33][C:23]([S:22][C:10]2[CH:9]=[C:8]([C:36]#[C:35][C:37]3[CH:38]=[CH:39][C:40]([S:43]([CH3:46])(=[O:45])=[O:44])=[CH:41][CH:42]=3)[CH:13]=[C:12]([O:14][CH2:15][CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[CH:11]=2)=[CH:24][C:25]=1[CH3:34])[CH3:2]

Participants

9

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 220426121-Ethynyl-4-(methanesulfonyl)benzeneHCID 67171784HCID 67171784, compound

Product 1

HCID 67170987HCID 67170987, compound

Reagents, catalysts & solvents 4

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

Procedure

[4-(3-Bromo-5-cyclohexylmethoxy-phenylsulfanyl)-2-methyl-phenoxy]-acetic acid ethyl acetate (0.1 g; 0.203 mmol), 1-Ethynyl-4-methanesulfonyl-benzene (0.109 g; 0.61 mmol), bis(triphenylphosphine)palladium (II) chloride (11.4 mg; 0.016 mmol) and copper iodide (2.3 mg; 0.06 mmol) were dissolved in a mixture of triethylamine (2 mL) and DMF (2 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 (Metode A). Yield: 90 mg. HPLC-MS: m/z: 593.5 (M+H)+; Rt: 3.04 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-529388810aaa4ec19987391c3b57c9e5
Source dataset
uspto-grants-2013_04
Patent number
US08426473B2

Reaction notes

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