* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; benzene; for 15h;Heating / reflux;
A mixture of the bromide from Step 1, 4-methylthiobenzene boronic acid (Li, et. al. J. Med. Chem. 1995, 38, 4570) (8.5 g), 2M aqueous sodium carbonate (60 mL) and palladium tetrakis(triphenylphosphine) (490 mg) in ethanol/benzene (100 mL, 1:1) was heated at reflux for 15 h. The mixture was cooled to r.t., diluted with water and extracted with ether. The organics were concentrated and the residue was subjected to stirred vigorously in ether/hexane for 1 h to provide, after filtration, the title compound (11.2 g) as a beige solid.
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; benzene; for 15h;Heating / reflux;
Step 2: 2-Amino-3-(4-methylthio)phenyl-5-trifluoromethylpyridine A mixture of the bromide from Step 1, 4-methylthiobenzene boronic acid (Li, et. al. J. Med. Chem. 1995, 38, 4570) (8.5 g), 2M aqueous sodium carbonate (60 mL) and palladium tetrakis(triphenylphosphine) (490 mg) in ethanol/benzene (100 mL, 1:1) was heated at reflux for 15 h. The mixture was cooled to r.t., diluted with water and extracted with ether. The organics were concentrated and the residue was subjected to stirred vigorously in ether/hexane for 1 h to provide, after filtration, the title compound (11.2 g) as a beige solid.
2-(2-carboxy-ethyl)-[1,3]oxazinane-3-carboxylic acid <i>tert</i>-butyl ester[ No CAS ]
2-{2-[1-(carboxymethyl-carbamoyl)-2-(4'-methylsulfanyl-biphenyl-3-yl)-ethylcarbamoyl]-ethyl}-[1,3]oxazinane-3-carboxylic acid <i>tert</i>-butyl ester[ No CAS ]
1,2,3,4-tetrafluoro-5-(4-fluorophenyl)-6-[4-(methylthio)phenyl]benzene[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
In ethanol; ethyl acetate; toluene;
Step 1 Preparation of 1,2,3,4-tetrafluoro-5-(4-fluorophenyl)-6-[4-(methylthio)phenyl]benzene Under nitrogen, 1 g of Pd(PPh3)4 was added to a stirred solution of 4.85 g (15.8 mmol) of <strong>[827-08-7]1,2-dibromo-3,4,5,6-tetrafluorobenzene</strong> (Aldrich), 2.65 g (18.9 mmol) of 4-fluorophenylboronic acid, and 3.17 g (18.9 mmol) of 4-methylthiophenylboronic acid (Example 1, Step 2) in 80 mL of toluene, 50 mL of ethanol, and 35 mL of 2M Na2 CO3. After vigorous stirring at reflux overnight, the solvent was removed in vacuo. The residue was dissolved in ethyl acetate, washed water, and dried over Na2 SO4. Concentration in vacuo gave 7.3 g of 1,2,3,4-tetrafluoro-5-(4-fluorophenyl)-6-[4-(methylthio)phenyl]benzene as a yellow oil which was used without further purification.
methyl 3,5-diamino-6-(4-(methylthio)phenyl)pyrazine-2-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
58%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In methanol; toluene;Inert atmosphere; Reflux;
General procedure: <strong>[1458-01-1]Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate</strong> 2 (1 eq.) was combined with K2CO3 (10 eq.), the appropriate (het)aryl boronic acid (1.5 eq.) and Pd(PPh3)4 (5 mol%) in a two-neck round bottom flask. The flask was connected to a condenser and purged with nitrogen. A 4:1 mixture of anhydrous toluene: MeOH (60 mL) was added via syringe and the reaction mixture was heated at reflux for 0.5-18 h. The mixture was allowed to cool to room temperature and filtered through Celite (10 x 3 cm, eluting with 3 x 20 mL EtOAc). The filtrate was evaporated to dryness and the residue purified by silica gel flash column chromatography using EtOAc/pet spirit.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
120K+ Compounds
Competitive Price
1-2 Day Shipping
