Water → N-benzyl-N-[2-(2-methoxy-5-trimethylsilanylethynyl-pyridin-3-yl)-5-trifluoromethyl-benzyl]-acetamide

HRID 554645Notes

Reaction equation

HRID 554645 reaction equation
[CH2:1]([N:8]([CH2:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=1[C:23]1[C:24]([O:30][CH3:31])=[N:25][CH:26]=[C:27](Br)[CH:28]=1)[C:9](=[O:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:32][Si:33]([C:36]#[CH:37])([CH3:35])[CH3:34].C(Cl)Cl.O>C(N(CC)CC)C.CN(C=O)C.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([N:8]([CH2:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=1[C:23]1[C:24]([O:30][CH3:31])=[N:25][CH:26]=[C:27]([C:37]#[C:36][Si:33]([CH3:35])([CH3:34])[CH3:32])[CH:28]=1)[C:9](=[O:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 66111TrimethylsilylacetyleneHCID 67212466N-benzyl-N-[2-(5-bromo-2-methoxy-pyridin-3-yl)-5-trifluoromethyl-benzyl]-acetamide

Product 1

HCID 67212387N-benzyl-N-[2-(2-methoxy-5-trimethylsilanylethynyl-pyridin-3-yl)-5-trifluoromethyl-benzyl]-acetamide

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

N-Benzyl-N-[2-(5-bromo-2-methoxy-pyridin-3-yl)-5-trifluoromethyl-benzyl]-acetamide (0.288 g, 0.58 mmol), (trimethylsilyl)acetylene (0.08 mL, 0.58 mmol), and copper iodide (0.011 g, 0.06 mmol) were combined in triethylamine (3.5 mL), and the solution was purged with N2 for 25 minutes. Dichlorobis(triphenylphosphine)palladium(II) (0.042 g, 0.06 mmol) was added, and the reaction was stirred at room temperature overnight. A few drops of DMF was added, and the reaction was stirred at 50° C. for 5 hours, and at 60° C. for 3 hours. The mixture was worked-up with CH2Cl2 and H2O, and the combined organic layers were dried, filtered, and concentrated. The residue was purified by silica gel chromatography (0-30% EtOAc in hexanes) to give N-benzyl-N-[2-(2-methoxy-5-trimethylsilanylethynyl-pyridin-3-yl)-5-trifluoromethyl-benzyl]-acetamide.

Workup

  1. customthe solution was purged with N2 for 25 minutes
  2. stirringthe reaction was stirred at 50° C. for 5 hours
  3. waitat 60° C. for 3 hours
  4. customthe combined organic layers were dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (0-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-a93728d588944735a3b8462e31acaa8e
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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