Triethylamine → tert-Butyl {5-[(trimethylsilyl)ethynyl]pyridin-3-yl}carbamate

HRID 1614978Notes

Reaction equation

HRID 1614978 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[N:6][CH:7]=1.C(N(CC)CC)C.[CH3:23][Si:24]([C:27]#[CH:28])([CH3:26])[CH3:25]>[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.O1CCCC1>[CH3:23][Si:24]([C:27]#[C:28][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[N:6][CH:7]=1)([CH3:26])[CH3:25]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 11403050tert-Butyl (5-bromopyridin-3-yl)carbamate

Product 1

HCID 57962266tert-Butyl {5-[(trimethylsilyl)ethynyl]pyridin-3-yl}carbamateYield 63%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Into a reaction flask were added tert-butyl (5-bromopyridin-3-yl)carbamate (3.0 g, 11.0 mmol), tetrahydrofuran (30 mL), and triethylamine (1.7 mL, 12 mmol). The reaction mixture was stirred under N2 bubbling for 5 min. (Trimethylsilyl)acetylene (1.60 g, 16.3 mmol), copper(I) iodide (84 mg, 0.44 mmol), and bis(triphenylphosphine)palladium(II) chloride (0.31 g, 0.44 mmol) were then added. The resultant mixture was heated at 50° C. overnight. The solvent was removed under vacuum and the residue was diluted with EtOAc and water. After separation, the organic layer was dried over Na2SO4 and concentrated under vacuum. The crude product was purified by silica gel column chromatography to give the desired product as a white powder (2.0 g, 63%). LCMS for C15H23N2O2Si (M+H)+: m/z=291.1.

Workup

  1. additionwere then added
  2. customThe solvent was removed under vacuum
  3. additionthe residue was diluted with EtOAc and water
  4. customAfter separation
  5. dry with materialthe organic layer was dried over Na2SO4
  6. concentrationconcentrated under vacuum
  7. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fc8f338c11f840e39c8c632386d453d5
Source dataset
uspto-grants-2014_07
Patent number
US08765727B2

Reaction notes

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