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Trimethylsilylacetylene → 2-(5-trimethylsilylethynyl-3-pyridyloxy)-N-(4-methylpent-2-yn-4-yl)butyramide

HRID 1374920
Notes
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Reaction equation

HRID 1374920 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:8][CH:9]([CH2:19][CH3:20])[C:10]([NH:12][C:13]([CH3:18])([CH3:17])[C:14]#[C:15][CH3:16])=[O:11])[CH:5]=[N:6][CH:7]=1.[CH3:21][Si:22]([C:25]#[CH:26])([CH3:24])[CH3:23]>C(N(CC)CC)C.C(OCC)C.[Cu]Cl>[CH3:21][Si:22]([C:25]#[C:26][C:2]1[CH:3]=[C:4]([O:8][CH:9]([CH2:19][CH3:20])[C:10]([NH:12][C:13]([CH3:18])([CH3:17])[C:14]#[C:15][CH3:16])=[O:11])[CH:5]=[N:6][CH:7]=1)([CH3:24])[CH3:23]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 66111Trimethylsilylacetylene2×HCID 21078374HCID 21078374, compound

Product 1

HCID 210784012-(5-trimethylsilylethynyl-3-pyridyloxy)-N-(4-methylpent-2-yn-4-yl)butyramide

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 3283Diethyl EtherSolvent
HCID 8471
Triethylamine
Solvent

Conditions

Temperature
90 °C

Procedure

2-(5-Bromo-3-pyridyloxy)-N-(4-methylpent-2-yn-4-yl)butyramide (0.40 g), trimethylsilylacetylene (0.24 ml), copper (I) chloride (0.015 g) and palladium dichloride bis(triphenyl)phosphine (0.030 g) in dry triethylamine (4 ml) were sealed in a glass tube and heated to 90° C. for 3 hours. The mixture was cooled to ambient temperature and stored for 18 hours. Further trimethylsilylacetylene (0.24 ml) and palladium dichloride bis(triphenyl)-phosphine (0.030 g) were added and the mixture re-heated in the sealed tube for another 5.5 hours. The reaction mixture was cooled to ambient temperature, stored for 72 hours, diluted with diethyl ether and washed with water (three times). The organic phase was separated, dried over magnesium sulphate and evaporated under reduced pressure to give a dark yellow gum, ca. 0.4 g, containing the required product, which was used in the next Stage without further purification.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. temperaturethe mixture re-heated in the sealed tube for another 5.5 hours
  3. temperatureThe reaction mixture was cooled to ambient temperature
  4. waitstored for 72 hours
  5. washwashed with water (three times)
  6. customThe organic phase was separated
  7. dry with materialdried over magnesium sulphate
  8. customevaporated under reduced pressure
  9. customto give a dark yellow gum, ca. 0.4 g

Sources & evidence

ORD record
ord-40abed4075dd486d9538de71bf5d5e8f
Source dataset
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07166621B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes