Acetonitrile → 3-(4-methylsulfonylphenyl)-4-phenyl-5-(trifluoromethyl)-1,2-oxazole
Reaction equation
Br[C:2]([F:25])([F:24])[C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[C:4]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[F-:26].[K+].CC#N>O>[CH3:17][S:14]([C:11]1[CH:12]=[CH:13][C:8]([C:5]2[C:4]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:3]([C:2]([F:25])([F:26])[F:24])[O:7][N:6]=2)=[CH:9][CH:10]=1)(=[O:16])=[O:15]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 7 (5.4 mg, 0.013 mmol), anhydrous KF (1.1 mg, 0.019 mmol), Kryptofix® 222 (7.0 mg, 0.019 mmol) and dry MeCN (1.0 mL) was refluxed for 50 min. The reaction mixture was diluted with H2O (5 mL) and passed through a Waters Sep-Pak® C-18 cartridge (1 mL). The cartridge was washed with H2O (3×3 mL) and with MeCN (3 mL). The MeCN eluate was purified by semi-preparative HPLC (Phenomenex® HPLC column: aqua, 5μ, C-18, 10 mm×250 mm) with MeCN—H2O (3:1) containing 0.075% TFA (5 mL/min). The fractions at 22-25 min were combined and concentrated to yield 8 (2.3 mg, 50%) as a colorless solid. The 1H NMR spectrum was identical with those reported (Habeeb, A. G.; Rao, P. N. P.; Knaus, E. E. Drug Dev. Res. 2000, 51, 273-286).
Workup
- temperaturewas refluxed for 50 min
- washThe cartridge was washed with H2O (3×3 mL) and with MeCN (3 mL)
- customThe MeCN eluate was purified by semi-preparative HPLC (Phenomenex® HPLC column: aqua, 5μ, C-18, 10 mm×250 mm) with MeCN—H2O (3:1)
- additioncontaining 0.075% TFA (5 mL/min)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-83a7c6c9cbcf45848ade9f882bdc49b7
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07329401B2
Reaction notes
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