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

HRID 1038604Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][O:8][C:9]2[C:10](OS(C(F)(F)F)(=O)=O)=[CH:11][C:12]([CH2:15][O:16][C:17](=[O:19])[CH3:18])=[N:13][CH:14]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:37][Si:38]([C:41]#[CH:42])([CH3:40])[CH3:39].O>C(#N)C.[Cu](I)I>[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][O:8][C:9]2[C:10]([C:42]#[C:41][Si:38]([CH3:40])([CH3:39])[CH3:37])=[CH:11][C:12]([CH2:15][O:16][C:17](=[O:19])[CH3:18])=[N:13][CH:14]=2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 45 °C

Procedure

(5-[(4-Methoxybenzyl)oxy]-4-{[(trifluoromethyl)sulfonyl]oxy}pyridin-2-yl)methylacetate (1.2 g, 2.78 mmol) was dissolved in acetonitrile (9.3 mL), added copper iodide (53 mg, 278 μmol), ditriphenylphosphine palladium (II) dichloride (98 mg, 139 μmol), triethylamine (8.0 mL) and trimethylsilyl acetylene (819 mg, 8.34 mmol) under an argon atmosphere, and under ice-cold conditions, and the mixture was stirred at 45° C. overnight. This operation was conducted for 4 lots, and the following treatments were conducted as a whole. The reaction solution was added water, and filtered through a pad of celite. The obtained filtrate was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. A crude product of the title compound (5.38 g) was obtained as a yellow oil.

Workup

filtrationfiltered through a pad of celite
extractionThe obtained filtrate was extracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-e1a69b817c5f419fb5c1b9d1e1a9dde6
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08551985B2

Reaction notes

Loading…