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2,2,2-trifluoro-N-(2-hydroxy-6-iodophenyl)acetamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
64%
With Oxone; In 1,4-dioxane; at 90.0℃;Schlenk technique; Inert atmosphere;
General procedure: A Schlenk tube was charged with Oxone (0.398 g, 0.648mmol) and trifloroacetic acid (0.099 mL, 1.296 mmol) in anhydrous dioxane (2 mL) under argon. To this mixture was added 2-fluoroaniline (0.06 g, 0.54 mmol), and the reaction mixture was heated to 90 C under argon until starting material was consumed. As the reaction progressed, the color turned from lightred to dark red. The mixture was then cooled to room temperature and washed with a saturated aqueous sodium bicarbonate.The mixture was extracted with EtOAc (2 × 20 mL) and the combined organic layers were dried over Na2SO4. After filtering andremoval of the solvent under reduced pressure in vacuo, theresidue was purified by silica gel (100-200 mesh) column chromatography(hexane-EtOAc, 9:1), to afford a pale-brown solid(65%) of 2-hydroxy-N-trifluoroacetanilides from 2-fluoroaniline(2a).
(1R,2R)-2-fluorocyclopropanecarboxylic acid (6-[2-ethyl-6-fluoro-4-(1-methyl-1H-pyrazol-4-yl)phenyl]methylamino}-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)amide[ No CAS ]
3.90.2. Step ii): 2-ethyl-6-fluoroaniline PdCl2dppf (0.1 eq, 375 mg), Cs2C03 (3 eq, 4.5 g) and <strong>[886762-73-8]6-fluoro-2-iodoaniline</strong> (1 eq, 1.1 g) are dissolved in dry DMF (50 mL) in a 250 mL round bottom flask. The suspension is degassed under nitrogen atmosphere for 10 min, followed by the addition of triethylborane (1M in hexane, 1.3 eq, 6.0 mL). The reaction is heated to 55C for 2 h, using a condenser. Upon completion of the reaction, as shown by LC-MS, the suspension is filtered over a Celite pad, which is washed with DCM. The filtrate is poured into water and extraction with DCM (3 x 50 mL) is performed. The combined organic layers are dried (Na2S04) and concentrated in vacuo. The residue is purified by silica chromatography (petroleum ether/EtOAc; 100:0 to 80:20) to give the desired product.
With iodine; silver sulfate; In ethanol; at 20.0℃;
3.90. Intermedi -Ethyl-6-fluoroaniline 3.90.1. Step i): 6-Fluoro-2-iodoaniline Iodine (1 eq, 4.6 g) is dissolved in EtOH (150 mL) at room temperature in a 250 mL round bottom flask and 2-fluoroaniline (1 eq, 2.0 g) and silver sulfate (1 eq, 5.6 g) are added. After overnight stirring of the suspension at room temperature, the silver salts are filtered off and the filtrate is concentrated under reduced pressure. The residue is dissolved in DCM and washed with sat. Na2S203 (3 x 50 mL). The organic layer is washed with sat. brine, dried over Na2S04 and purified via silica chromatography (petroleum ether/EtOAc; 100:0 to 50:50) to give the envisaged product.
2'-chloro-3-fluoro-[1,1'-biphenyl]-2-amine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
69%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrabutylammomium bromide; potassium carbonate; In 1,4-dioxane; water; at 130.0℃; for 1h;Microwave irradiation;
General procedure: Substituted 2-iodoaniline 1 (1.0 eq.), substituted phenylboronicacid 2 (1.2 eq.), K2CO3 (3.0 eq.), tetrabutylammonium bromide (0.1eq.), PdCl2(dppf) (0.1 eq.) and dioxane/H2O (9:1) (0.5 M) wereadded to a 10 mL microwave-vial. The vial was sealed with a capand placed in a Cem Discover-microwave cavity. After irradiation at130 C for 1 h and subsequent cooling, the solvent was removed invacuo. The residue was taken up into EtOAc (30 mL) and washedonce withwater and brine. The organic layerwas dried over MgSO4,filtered, and concentrated. The crude product was purified by flashcolumn chromatography using 0e10% EtOAc/petroleum benzine togive the biphenylamine product 3a-3aa.
tert-butyl ((4-fluorobenzo[d]thiazol-2-yl)methyl)carbamate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
91%
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); copper(II) oxide; In N,N-dimethyl-formamide; at 90.0℃; for 1h;Sealed tube;
A solution of 2-fluoro-6-iodoaniline (200 mg, 0.844 mmol) in DMF (0.5 mL) was added to amixture of <strong>[89226-13-1]tert-butyl (2-amino-2-thioxoethyl)carbamate</strong> (209 mg, 1.10 mmol), CuO (101 mg,1.27 mmol), Pd2(dba)3 (77 mg, 0.084 mmol), and dppf (94 mg, 0.169 mmol) in DMF (1 mL).The sealed vial was stirred at 90 C for 1 h and cooled to RT. FCC (10-30% EtOAc inisohexane) afforded the title compound as a yellow solid (217 mg, 9 1%). M/z 305 (M+Na).
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