| 74% |
With Dess-Martin periodane; In dichloromethane; at 20℃; for 0.333333h; |
A solution of Example 34B (3.89 g, 22.0 mmol) in CH2Cl2 (10 mL) was added to a deoxygenated solution of Dess-Martin periodinane (1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one, 10.3 g, 24.2 mmol) in CH2Cl2 (73 mL) in one portion. The reaction was stirred under nitrogen at ambient temperature for about 20 minutes after which a solid formed. The reaction was diluted with 50 mL CH2Cl2 and carefully quenched with approximately 30 mL of saturated NaHCO3 solution. The undissolved solid was filtered, and the filtrate was transferred to a separatory funnel. The aqueous phase was extracted with CH2Cl2, and the combined organic layer was washed with brine, dried over Na2SO4, filtered, and evaporated at reduced pressure to 50 mL. This solution was then loaded on silica gel (Analogix 40*150 column) and eluted with 25% to 50% EtOAc/hexanes. The result was 2.86 g (74%) of the title compound as a clear oil, which solidified on standing. 1H NMR (300 MHz, CDCl3) delta 10.15 (s, 1H), 9.06 (m, 1H), 8.15 (m, 1H), 8.09 (d, J=8.1, 1H). |
|
With manganese(IV) oxide; In chloroform; at 20℃; for 15h;Heating / reflux; |
EXAMPLE 18; trans-N-[4-(4,5-Dichloro-imidazol-1-yl)-3-trifluoromethyl-phenyl]-3-(5-trifluoromethyl-pyridin-2-yl)-acrylamide (Cpd 235) A. To a solution of compound 18a (3.84 g, 21.7 mmol), in 25 mL CHCl3 was added manganese dioxide (MnO2) (8.04 g). After stirring at ambient temperature for 15 hours the suspension was heated at reflux under a nitrogen atmosphere for an additional 23 hours. The reaction mixture was filtered over a pad of celite and the filter cake washed with additional CHCl3. The filtrate was evaporated in vacuo to yield the product, compound 18b as an orange oil. MS: M+H+=175.8, 1H NMR (CDCl3): delta 10.15 (s, 1H), 9.06 (s, 1H), 8.17-8.06 (m, 2H). |
|
|
Intermediate 13: 2-[5-(Trifluoromethyl)pyridin-2-yl]methyl}cyclopentan-1-amine Step (i): 5-(Trifluoromethyl)pyridine-2-carbaldehyde Dess-Martin periodinane (CAS number 87413-09-0; 13.17 g, 31.10 mmol) was added to a solution of <strong>[31181-84-7][5-(trifluoromethyl)pyridin-2-yl]methanol</strong> (CAS number 31181-84-7; 5.00 g, 28.2 mmol) in DCM (60 ml). The reaction was stirred at room temperature for 18 hours and then a saturated solution of sodium thiosulfate (aq, 100 ml) was added. The reaction was stirred for 45 min at room temperature and then phases separated. The aqueous phase was further extracted with DCM (60 ml) and the combined organics were washed with a saturated solution of sodium bicarbonate (aq, 60 ml), filtered through a hydrophobic frit and concentrated in vacuo. The crude product was purified by column chromatography (silica, 0-20% ethyl acetate/petrol) to afford the title compound. MS ES+: 176 |
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
120K+ Compounds
Competitive Price
1-2 Day Shipping
