Triethylamine → (5R)-3-{3-Fluoro-4-[(trimethylsilyl)ethynyl]phenyl}-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one

HRID 1371834Notes

Reaction equation

[C:1]([Si:3]([CH3:6])([CH3:5])[CH3:4])#[CH:2].C(N(CC)CC)C.[F:14][C:15]1[CH:16]=[C:17]([N:22]2[CH2:26][C@H:25]([CH2:27][N:28]3[CH:32]=[C:31]([CH3:33])[N:30]=[N:29]3)[O:24][C:23]2=[O:34])[CH:18]=[CH:19][C:20]=1I>[Cu](I)I>[F:14][C:15]1[CH:16]=[C:17]([N:22]2[CH2:26][C@H:25]([CH2:27][N:28]3[CH:32]=[C:31]([CH3:33])[N:30]=[N:29]3)[O:24][C:23]2=[O:34])[CH:18]=[CH:19][C:20]=1[C:2]#[C:1][Si:3]([CH3:6])([CH3:5])[CH3:4]

Participants

Conditions

Temperature: 60 °C

Procedure

Ethynyl(trimethyl)silane (432 mg, 4.4 mmol), copper iodide(76 mg, 0.4 mmol), triethylamine (2.02 g, 20 mmol) and palladium tetrakis triphenylphosphine (231 mg, 0.2 mmol) were added to a solution of (5R)-3-(3-fluoro-4-iodophenyl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one (WO2003072575) (Intermediate 2,1.61 g, 4.0 mmol) in a sealed reaction vessel. The reaction mixture was stirred at 60° C. over night, then cooled down to room temperature and filtered through celite. The filtrate was concentrated and purified by flash chromatography on silica gel with 30% hexanes in ethyl acetate. The product was obtained as a yellowish solid (1.4 g).

Workup

temperaturecooled down to room temperature
filtrationfiltered through celite
concentrationThe filtrate was concentrated
custompurified by flash chromatography on silica gel with 30% hexanes in ethyl acetate

Sources & evidence

ORD record: ord-c41b49042e9743578d6b980fa39a5a5c
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157482B2

Reaction notes

Loading…