Water → Cyclopropanecarboxylic acid ethyl-[2-(2-methoxy-5-trimethylsilanylethynyl-pyridin-3-yl)-5-trifluoromethyl-benzyl]-amide

HRID 554617Notes

Reaction equation

HRID 554617 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:10]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][C:11]=2[CH2:12][N:13]([CH2:19][CH3:20])[C:14]([CH:16]2[CH2:18][CH2:17]2)=[O:15])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[CH3:29][Si:30]([C:33]#[CH:34])([CH3:32])[CH3:31].C(Cl)Cl.O>C(N(CC)CC)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>[CH2:19]([N:13]([CH2:12][C:11]1[CH:21]=[C:22]([C:25]([F:28])([F:27])[F:26])[CH:23]=[CH:24][C:10]=1[C:4]1[C:5]([O:8][CH3:9])=[N:6][CH:7]=[C:2]([C:34]#[C:33][Si:30]([CH3:32])([CH3:31])[CH3:29])[CH:3]=1)[C:14]([CH:16]1[CH2:18][CH2:17]1)=[O:15])[CH3:20]

Participants

8

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 66111TrimethylsilylacetyleneHCID 67212469Cyclopropanecarboxylic acid [2-(5-bromo-2-methoxy-pyridin-3-yl)-5-trifluoromethyl-benzyl]-ethyl-amide

Product 1

HCID 67212431Cyclopropanecarboxylic acid ethyl-[2-(2-methoxy-5-trimethylsilanylethynyl-pyridin-3-yl)-5-trifluoromethyl-benzyl]-amide

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

Cyclopropanecarboxylic acid [2-(5-bromo-2-methoxy-pyridin-3-yl)-5-trifluoromethyl-benzyl]-ethyl-amide (0.215 g, 0.47 mmol), (trimethylsilyl)acetylene (0.07 mL, 0.47 mmol), and copper iodide (0.012 g, 0.05 mmol) were combined in triethylamine (2 mL), and the solution was purged with N2 for 25 minutes. Dichlorobis(triphenylphosphine)palladium(II) (0.039 g, 0.05 mmol) was added, and the reaction was stirred at room temperature overnight. 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 (0-100% EtOAc in hexanes) to give cyclopropanecarboxylic acid ethyl-[2-(2-methoxy-5-trimethylsilanylethynyl-pyridin-3-yl)-5-trifluoromethyl-benzyl]-amide.

Workup

  1. customthe solution was purged with N2 for 25 minutes
  2. customthe combined organic layers were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-1a16ae84a6cb4c518fb12ce9d2b61434
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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