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

HRID 541751Notes

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.[CH3:16][Si:17]([C:20]#[CH:21])([CH3:19])[CH3:18].C(N(CC)CC)C>[Cu]I.C1COCC1>[CH3:16][Si:17]([C:20]#[C:21][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)([CH3:19])[CH3:18]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of tert-butyl (5-bromopyridin-3-yl)carbamate (3.00 g, 11.0 mmol) and THF (30 mL) was added (trimethylsilyl)acetylene (1.60 g, 16.3 mmol), (triphenylphosphine)palladium(II) chloride (0.31 g, 0.44 mmol), copper(I) iodide (84 mg, 0.44 mmol) and triethylamine (1.7 mL, 12 mmol) under nitrogen atmosphere. The mixture was heated at 50° C. overnight. The solvent removed in vacuo. The residue was diluted with EtOAc and water. The organic layer was separated, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography to yield the desired product (2.0 g, 63%). LCMS calculated for C15H23N2O2Si(M+H)+: m/z=291.1.

Workup

customThe solvent removed in vacuo
additionThe residue was diluted with EtOAc and water
customThe organic layer was separated
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude residue was purified by flash column chromatography

Sources & evidence

ORD record: ord-2197df9b4bdc4389bcef60ce5a79c223
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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