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Triethylamine → {5-({[4-(Methyloxy)phenyl]methyl}oxy)-4-[(trimethylsilyl)ethynyl]-2-pyridinyl}methyl acetate

HRID 15327
Notes
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Reaction equation

HRID 15327 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10](OS(C(F)(F)F)(=O)=O)[C:9]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=[CH:8][N:7]=1)(=[O:3])[CH3:2].C(N(CC)CC)C.[CH3:37][Si:38]([C:41]#[CH:42])([CH3:40])[CH3:39]>C(#N)C.[Cu]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>[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10]([C:42]#[C:41][Si:38]([CH3:40])([CH3:39])[CH3:37])[C:9]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=[CH:8][N:7]=1)(=[O:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 57423118(5-((4-Methoxybenzyl)oxy)-4-(((trifluoromethyl)sulfonyl)oxy)pyridin-2-yl)methyl acetate

Product 1

HCID 57423117{5-({[4-(Methyloxy)phenyl]methyl}oxy)-4-[(trimethylsilyl)ethynyl]-2-pyridinyl}methyl acetateYield 96%

Reagents, catalysts & solvents 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 178418476HCID 178418476, compoundCatalyst
HCID 6342AcetonitrileSolvent

Conditions

Temperature
45 °C

Procedure

(5-({[4-(Methyloxy)phenyl]methyl}oxy)-4-{[(trifluoromethyl)sulfonyl]oxy}-2-pyridinyl)methyl acetate (10 g, 23 mmol) (for a synthesis see WO2004058144, Example 60(d)) was dissolved in acetonitrile (400 ml) and triethylamine (65 ml) and treated with trimethylsilyl acetylene (10 ml, 69 mmol). The mixture was then degassed several times and put under an atmosphere of argon. Copper(I) iodide (0.44 g, 2,3 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.645 g, 0.9 mmol) was added and the mixture heated at 45° C. for 18 h. The mixture was allowed to cool and filtered. The filtrate was concentrated in vacuo and the residue partitioned between ethyl acetate and water. The organic layer was dried then evaporated to dryness. Chromatography on silica gel eluting with 40-60 petrol and ethyl acetate gradient provided the desired compound (8.45 g, 96%).

Workup

  1. customThe mixture was then degassed several times
  2. temperatureto cool
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue partitioned between ethyl acetate and water
  6. customThe organic layer was dried
  7. customthen evaporated to dryness

Sources & evidence

ORD record
ord-dab63cbb9d81434f9c369ca7618f597e
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07732461B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes