3-(5-Fluoro-2-pyridyl)-5-(3-bromo-5-fluorophenyl)-1,2,4-oxadiazole → 3-(5-Fluoro-2-pyridyl)-5-(3-fluoro-5-(1-trityl-1H-imidazol-4-yl)phenyl)-1,2,4-oxadiazole

HRID 431981Notes

Reaction equation

C([Sn](CCCC)(CCCC)[C:6]1[N:7]=[CH:8][N:9]([C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=1)CCC.[F:38][C:39]1[CH:40]=[CH:41][C:42]([C:45]2[N:49]=[C:48]([C:50]3[CH:55]=[C:54]([F:56])[CH:53]=[C:52](Br)[CH:51]=3)[O:47][N:46]=2)=[N:43][CH:44]=1>O1CCCC1>[F:38][C:39]1[CH:40]=[CH:41][C:42]([C:45]2[N:49]=[C:48]([C:50]3[CH:51]=[C:52]([C:6]4[N:7]=[CH:8][N:9]([C:11]([C:12]5[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=5)([C:24]5[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=5)[C:18]5[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=5)[CH:10]=4)[CH:53]=[C:54]([F:56])[CH:55]=3)[O:47][N:46]=2)=[N:43][CH:44]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To the solution of 4-Tributylstannyl-1-trityl-1H-imidazole (106 mg, 0.18 mmol) in tetrahydrofuran (5 ml) added 3-(5-Fluoro-2-pyridyl)-5-(3-bromo-5-fluorophenyl)-1,2,4-oxadiazole (50.0 mg, 0.15 mmol) and tetrakis(triphenylphoshine)palladium (0) (17.1 mg, 0.01 mmol), sequentially. The resulting brownish yellow reaction mixture was heated at 100° C. under argon overnight. The reaction mixture was cooled to room temperature and concentrated in-vacuo. The residue was purified on silica gel using 30% ethyl acetate in hexanes to isolate 3-(5-Fluoro-2-pyridyl)-5-(3-fluoro-5-(1-trityl-1H-imidazol-4-yl)phenyl)-1,2,4-oxadiazole (20.0 mg).

Workup

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated in-vacuo
customThe residue was purified on silica gel using 30% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-b34d2db9e710479cac51d3ecdc2a101b
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06660753B2

Reaction notes

Loading…