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Limited Quantity
USD 15-60
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USD 80+
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Structure of 654-76-2 * Storage: {[proInfo.prStorage]}
* 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.
Reference：
[1] Journal of Medicinal Chemistry, 1998, vol. 41, # 10, p. 1598 - 1612
4
[ 88-16-4 ]
[ 654-76-2 ]
Reference：
[1] Journal of Organic Chemistry, 1961, vol. 26, p. 2707 - 2710
5
[ 67-56-1 ]
[ 777-37-7 ]
[ 654-76-2 ]
Reference：
[1] Journal of Organic Chemistry, 1961, vol. 26, p. 2707 - 2710
6
[ 654-76-2 ]
[ 1548-61-4 ]
Yield
Reaction Conditions
Operation in experiment
83%
With hydrogen bromide In water; acetic acid for 96 h; Heating / reflux
A solution of 6-methoxy-5-nitrobenzotrifluoride (24.73 g, 110.7 mmol) in acetic acid (260 ml) and aqueous HBr solution (62percent, 130 ml) was heated to reflux for 96 h, cooled, evaporated and taken up in aqueous saturated NaHCO3 solution/Et2O (3x). The organic phases were washed with aqueous 10percent NaCl, dried over Na2SO4 and evaporated to yield 19.27 g (83percent) of 4-nitro-2-trifluoromethyl-phenol as yellow solid, MS: 207 (M+), MP: 103-104 C.
65%
With lithium chloride In N,N-dimethyl-formamide for 6.5 h; Heating / reflux
A mixture of l-methoxy-4-nitro-2- (trifluoromethyl) benzene (10.29 g, 46.5 mmol) , lithium chloride (5.92 g, 140 mmol) and N, N-dimethylformamide (46.5 mL) was heated under reflux for 6.5 hr. After cooling to room temperature, 10percent aqueous sodium hydroxide solution (230 mL) was added, and the mixture was washed with ethylether (χ2) . The aqueous solution was acidified with 10percent hydrochloric acid, and extracted with ether (χ2) . The- extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was purified by column chromatography (silica gel, hexane/ethyl acetate=80/20) to give the title compound (6.20 g, 65percent) .1H-NMR (CDCl3, 300 MHz) δ V.08 (IH, d, J = 9.0 Hz), 8.32 (IH, dd, J = 9.0, 2.7 Hz) , 8.48 (IH, d, J = 2.7 Hz) .
3.5 g
at 160℃; for 5 h;
Lithium chloride (2.30 g) was added to a solution of 1-methoxy-4-nitro-2-(trifluoromethyl)benzene (4 g) in N,N-dimethylformamide (40 ml) at room temperature. The reaction mixture was stirred at 160 °C for 5 h. After cooling to rt, the solution was diluted with EtOAc (300 ml). The mixture was washed with water (100 ml * 2) and brine (100 ml), dried and concentrated to give 4-nitro-2-(trifluoromethyl)phenol (3.5 g) as a yellow solid.
Reference：
[1] Journal of Materials Chemistry, 2009, vol. 19, # 39, p. 7208 - 7215
[2] Patent: US2004/248951, 2004, A1, . Location in patent: Page 16
[3] Patent: WO2007/4749, 2007, A1, . Location in patent: Page/Page column 150
[4] Journal of Organic Chemistry, 1962, vol. 27, p. 4660 - 4662
[5] Patent: WO2005/80340, 2005, A1, . Location in patent: Page/Page column 50
[6] Patent: WO2012/100734, 2012, A1, . Location in patent: Page/Page column 28
[7] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 17, p. 5293 - 5302
7
[ 654-76-2 ]
[ 53903-51-8 ]
Reference：
[1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 17, p. 5293 - 5302
[2] Patent: WO2012/100734, 2012, A1,
8
[ 654-76-2 ]
[ 393-15-7 ]
Yield
Reaction Conditions
Operation in experiment
100%
With hydrogen In methanol; water at 20℃; for 3.5 h;
To a solution of 2-methoxy-5-nitrobenzotrifluoride (5.08 g, 23.0 mmol) in methanol (200 ml) was added 10percent Pd-C (containing 50percent water, 250 mg), and the resulting mixture was stirred for 3.5 hours under a hydrogen atmosphere at room temperature and atmospheric pressure while maintaining the temperature. The mixture was filtered by the use of Celite and the filtrate was concentrated to dryness under reduced pressure to obtain 4-methoxy-3-(trifluoromethyl)aniline (4.67 g, 100percent). MS : m/z = 192 (M + 1)
99%
for 4 h;
1-Methoxy-4-nitro-2-trifluoromethyl-benzene (10 g, 45 mmol) was hydrogenated in a Paar apparatus with shaking at 50 psi for 4 hours, with 1 g 10 wt percent Pd/C. The reaction mixture was filtered through celite, and the filtrate was evaporated in vacuo to give 8.6 g 4-Methoxy-3-trifluoromethyl-phenylamine, 99percent, as a solid.
99%
for 4 h;
1-Methoxy-4-nitro-2-trifluoromethyl-benzene (10 g, 45 mmol) was hydrogenated in a Paar apparatus with shaking at 50 psi for 4 hours, with 1 g 10 wt percent Pd/C. The reaction mixture was filtered through celite, and the filtrate was evaporated in vacuo to give 8.6 g 4-Methoxy-3-trifluoromethyl-phenylamine, 99percent, as a solid.
With hydrogen;palladium 10% on activated carbon; In methanol; water; at 20℃; under 760.051 Torr; for 3.5h;
To a solution of 2-methoxy-5-nitrobenzotrifluoride (5.08 g, 23.0 mmol) in methanol (200 ml) was added 10% Pd-C (containing 50% water, 250 mg), and the resulting mixture was stirred for 3.5 hours under a hydrogen atmosphere at room temperature and atmospheric pressure while maintaining the temperature. The mixture was filtered by the use of Celite and the filtrate was concentrated to dryness under reduced pressure to obtain 4-methoxy-3-(trifluoromethyl)aniline (4.67 g, 100%). MS : m/z = 192 (M + 1)
99%
With hydrogen;palladium 10% on activated carbon; under 2585.81 Torr; for 4h;
<strong>[654-76-2]1-Methoxy-4-nitro-2-trifluoromethyl-benzene</strong> (10 g, 45 mmol) was hydrogenated in a Paar apparatus with shaking at 50 psi for 4 hours, with 1 g 10 wt % Pd/C. The reaction mixture was filtered through celite, and the filtrate was evaporated in vacuo to give 8.6 g 4-Methoxy-3-trifluoromethyl-phenylamine, 99%, as a solid.
99%
With hydrogen;palladium 10% on activated carbon; under 2585.81 Torr; for 4h;
<strong>[654-76-2]1-Methoxy-4-nitro-2-trifluoromethyl-benzene</strong> (10 g, 45 mmol) was hydrogenated in a Paar apparatus with shaking at 50 psi for 4 hours, with 1 g 10 wt % Pd/C. The reaction mixture was filtered through celite, and the filtrate was evaporated in vacuo to give 8.6 g 4-Methoxy-3-trifluoromethyl-phenylamine, 99%, as a solid.
With hydrogen;nickel; In methanol; under 1050.11 - 3750.38 Torr; for 15h;
The title compound is prepared from <strong>[654-76-2]1-methoxy-4-nitro-2-trifluoromethyl-benzene</strong> (1 g, 4.43 [MMOL)] by hydrogenation [(5-] 1.4 bar) in the presence of Raney-Ni (0.3 g) in MeOH (20 mL) during 15 h. The product is isolated by filtration of the reaction suspension over Hyflo and evaporation of the solvent under reduced pressure to give compound of Stage 149.1 as a beige solid : M+H = 191.9 ; Rf [(ACOET/HEXANE] = 1 : 1): 0.33.
A suspension of <strong>[654-76-2]4-methoxy-3-trifluoromethyl-nitrobenzene</strong> (2.2 g) and iron powder (1.68 g) in ethanol (35 mL) and water (15 mL) is treated with a solution of concentrated hydrochloric acid (0.42 mL) in ethanol (6 mL) and water (3 mL) and the mixture is heated to reflux for approximately 1 hour. The mixture is then cooled, filtered, and concentrated under reduced pressure. The resulting oil is dissolved in ethyl acetate and extracted three times with 5% aqueous hydrochloric acid. The pooled acidic extracts are then cooled in an ice bath and basified with solid potassium carbonate, then extracted with ethyl acetate. These organic extracts are washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, concentrated under reduced pressure, then passed through a short column of silica gel (ethyl acetate is used as the eluant) to provide the desired compound as an amber oil.
With tin(ll) chloride; In ethyl acetate; at 20℃; for 5h;Heating / reflux;
[0185] 1-Methoxy-4-nitro-2-trifluoromethylbenzene 68 (0.1 mol) and SnCl2 (1 mol) was mixed in EtOAc. The mixture was stirred at rt for 2 hrs and then refluxed for 3 hrs until TLC indicated the completion of the reaction. The reaction mixture was cooled and quenched with aqueous NaHC03. The solid was filtered through a celite pad and washed with EtOAc. The organic layer of the filtrate was collected, dried and concentrated to afford the corresponding aniline. To the aniline (0.05 mol) in methylene chloride (200mL) was added Et3N and (CF3CO) 20 at 0C. The reaction was allowed to warm to 25C with stirring. The reaction was then worked up between EtOAc and water. The organic layer was dried and concentrated. The residue was purified on silica gel column to afford 70. This material is dissolved in methylene chloride (100 mL) and the solution was cooled to-78C. Boron tribromide (0.1 mol) was added. The mixture was warmed to room temperature. Water was added, and the organic phase was dried and concentrated. Chromatography afforded the title compound 71.
With hydrogen bromide; In water; acetic acid; for 96h;Heating / reflux;
A solution of 6-methoxy-5-nitrobenzotrifluoride (24.73 g, 110.7 mmol) in acetic acid (260 ml) and aqueous HBr solution (62%, 130 ml) was heated to reflux for 96 h, cooled, evaporated and taken up in aqueous saturated NaHCO3 solution/Et2O (3x). The organic phases were washed with aqueous 10% NaCl, dried over Na2SO4 and evaporated to yield 19.27 g (83%) of 4-nitro-2-trifluoromethyl-phenol as yellow solid, MS: 207 (M+), MP: 103-104 C.
65%
With lithium chloride; In N,N-dimethyl-formamide; for 6.5h;Heating / reflux;
A mixture of l-methoxy-4-nitro-2- (trifluoromethyl) benzene (10.29 g, 46.5 mmol) , lithium chloride (5.92 g, 140 mmol) and N, N-dimethylformamide (46.5 mL) was heated under reflux for 6.5 hr. After cooling to room temperature, 10% aqueous sodium hydroxide solution (230 mL) was added, and the mixture was washed with ethylether (chi2) . The aqueous solution was acidified with 10% hydrochloric acid, and extracted with ether (chi2) . The- extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was purified by column chromatography (silica gel, hexane/ethyl acetate=80/20) to give the title compound (6.20 g, 65%) .1H-NMR (CDCl3, 300 MHz) delta V.08 (IH, d, J = 9.0 Hz), 8.32 (IH, dd, J = 9.0, 2.7 Hz) , 8.48 (IH, d, J = 2.7 Hz) .
With boron tribromide; In dichloromethane; at -78℃;
[0184] 1-Fluoro-4-nitro-2-trifluoromethylbenzene 67 (0.1 mol), was dissolved in tetrahydrofuran (100 mL). The solution was cooled to 0C and sodium methoxide (0.1 mol) was added. The reaction was warmed to room temperature over 2 hours. Water and ethyl acetate were added. The organic phase was dried and concentrated to afford l-methoxy-4- nitro-2-trifluoromethylbenzene 68. This material was dissolved in methylene chloride (100 mL) and the solution was cooled to-78C. Boron tribromide (0.1 mol) was added. The mixture was warmed to room temperature. Water was added, and the organic phase was dried and concentrated. Chromatography then afforded the title compound 69.
Example 19; Ar-(5-(4-chloro-2-(trifluoromethyl)phenoxy)-4-(3-cyanophenyl)thiazol-2-yl)-2-(4- (ethylsulfonyl)phenyl)acetamide; Step 1:; Lithium chloride (2.30 g) was added to a solution of l-methoxy-4-nitro-2- (trifluoromethyl)benzene (4 g) in NN-dimethylformamide (40 mL) at room temperature. The reaction mixture was stirred at 160 C for 5 hours. After cooling to RT, the solution was diluted with EtOAc (300 mL). The mixture was washed with water (100 mL x 2) and brine (100 mL), dried and concentrated to give 4-nitro-2-(trifluoromethyl)phenol (3.5 g) as a yellow solid.
3.5 g
With N,N-dimethyl-formamide; lithium chloride; at 160℃; for 5h;
Lithium chloride (2.30 g) was added to a solution of <strong>[654-76-2]1-methoxy-4-nitro-2-(trifluoromethyl)benzene</strong> (4 g) in N,N-dimethylformamide (40 ml) at room temperature. The reaction mixture was stirred at 160 C for 5 h. After cooling to rt, the solution was diluted with EtOAc (300 ml). The mixture was washed with water (100 ml * 2) and brine (100 ml), dried and concentrated to give 4-nitro-2-(trifluoromethyl)phenol (3.5 g) as a yellow solid.
With potassium tert-butylate; In N,N-dimethyl-formamide; at -10℃; for 1h;
A mixture of 1 -methoxy-4-nitro-2-(trifluoromethyl)benzene [CAS 654-76-2] (24.5 g, 1 10.8 mmol) and 4-chlorophenoxyacetonitrile [CAS 3598-13-8] (20.4 g, 121 .9 mmol) in DMF (100 mL) was added dropwise over 30 min to a stirred solution of tBuOK (27.35 g, 243.7 mmol) in DMF (100 mL) at -10C. After addition, the purple solution was maintained at -10C for 1 h. 500 mL of ice-water and 500 mL of 6N HCI were added and the precipitate was filtered off, washed with water and dried under reduced pressure to afford 40.4 g of 2-(5-methoxy-2-nitro-4- (trifluoromethyl)phenyl)acetonitrile 5a (used as such in the next step).
40.4 g
With potassium tert-butylate; In N,N-dimethyl-formamide; at -10℃; for 1.5h;
A mixture of 1 -methoxy-4-nitro-2-(trifluoromethyl)benzene [CAS 654-76-2] (24.5 g, 1 10.8 mmol) and 4-chlorophenoxyacetonitrile [CAS 3598-13-8] (20.4 g, 121 .9 mmol) in DMF (100 mL) was added dropwise over 30 min to a stirred solution of fBuOK (27.4 g, 243.7 mmol) in DMF (100 mL) at -10C. After addition, the purple solution was maintained at -10C for 1 h. Ice-water (500 mL) and 6N HCI (500 mL) were added and the precipitate was filtered off, washed with water and dried under vacuum to afford 2-(5-methoxy-2-nitro-4-(trifluoromethyl)- phenyl)acetonitrile 7a (40.4 g) which was used as such in the next step.
With potassium tert-butylate; In N,N-dimethyl-formamide; at -10℃; for 1.5h;
A mixture of 1 -methoxy-4-nitro-2-(trifluoromethyl)benzene [CAS 654-76-2] (24.5 g, 1 10.8 mmol) and 4-chlorophenoxyacetonitrile [CAS 3598-13-8] (20.4 g, 121 .9 mmol) in DMF (100 mL) was added dropwise over 30 min to a stirred solution of tBuOK (27.35 g, 243.7 mmol) in DMF (100 mL) at -10C. After addition, the purple solution was maintained at -10C for 1 h. 500 mL of ice-water and 500 mL of 6N HCI were added and the precipitate was filtered off, washed with water and dried under reduced pressure to afford 40.4 g of 2-(5-methoxy-2-nitro-4- (trifluoromethyl)phenyl)acetonitrile 2a (used as such in the next step).
40.4 g
A mixture of <strong>[654-76-2]1-methoxy-4-nitro-2-(trifluoromethyl)benzene</strong> [CAS 654-76-2] (24.5 g,110.8 mmol) and 4-chiorophenoxyacetonitrile [CAS 3598-13-8] (20.4 g, 121.9 mmol) in DMF (100 mL) was added dropwise over 30 mm to a stirred solution of tBuOK (27.35 g, 243.7 mmol) in DMF (100 mL) at -10C. After addition, the purple solution was maintained at 100C for 1 h. 500 mL of ice-water and 500 mL of 6NHCI were added and the precipitate was filtered off, washed with water and dried under reduced pressure to afford 40.4 g of 2-(5-methoxy-2-nitro-4- (trifluoromethyl)phenyl)acetonitrile 2e (used as such in the next step).
A mixture of 1 -methoxy-4-nitro-2-(trifluoromethyl)benzene [CAS 654-76-2] (24.5 g, 1 10.8 mmol) and 4-chlorophenoxyacetonitrile [CAS 3598-13-8] (20.4 g, 121 .9 mmol) in DMF (100 ml_) was added dropwise over 30 min to a stirred solution of tBuOK (27.35 g, 243.7 mmol) in DMF (100 ml_) at -10C. After addition, the purple solution was maintained at -10C for 1 h. 500 ml_ of ice-water and 500 ml_ of 6N HCI were added and the precipitate was filtered off, washed with water and dried under reduced pressure to afford 40.4 g of 2-(5-methoxy-2-nitro-4-(trifluoromethyl)- phenyl)acetonitrile 20a (used as such in the next step).
Example 2:3-(5-Methoxy-6-trifluoromethyl-lH-indol-2-yl)-4-phenethylamino-lH-pyridin-2- one; a) (5-Methoxy-2-nitro-4-trifluorornethyl-benzyl)-trimethyl-silane; A solution of l-methoxy-4-nitro-2-trifluorornethyl-benzene (LOg, 4.52 mmol) in THF (60 ml) is cooled to -75 0C under inert gas atmosphere and trimethylsilylmethyl-rnagnesiurn chloride (4.52 ml of a 1 M solution in <n="29"/>diethylether) is slowly added. After continuing stirring at this temperature for one hour, a solution of 2,3-dichloro-5,6-dicyano-l,4-benzochinon (DDQ; 1.23 g, 5.43 mmol) in THF (25 ml) is added. While stirring, the resulting solution is slowly warmed up to 0 0C, and stirring is continued at this temperature for another hour. The reaction mixture is poured in an aqueous solution of acetic acid (5 vol.-%, 50 ml), extracted with dichloromethane and worked up. The two formed isomers are separated by silica gel chromatography. Yield: 330 mg (23.7 %).1H-NMR (400 MHz, D6-DMSO): delta= 8.23 (s, IH), 7.15 (s, IH), 3.98 (s, 3H), 2.77 (s, 2H), 0.01 (s, 9H)
[0184] 1-Fluoro-4-nitro-2-trifluoromethylbenzene 67 (0.1 mol), was dissolved in tetrahydrofuran (100 mL). The solution was cooled to 0C and sodium methoxide (0.1 mol) was added. The reaction was warmed to room temperature over 2 hours. Water and ethyl acetate were added. The organic phase was dried and concentrated to afford l-methoxy-4- nitro-2-trifluoromethylbenzene 68. This material was dissolved in methylene chloride (100 mL) and the solution was cooled to-78C. Boron tribromide (0.1 mol) was added. The mixture was warmed to room temperature. Water was added, and the organic phase was dried and concentrated. Chromatography then afforded the title compound 69.
With hydrogenchloride; In ethanol; water; ethyl acetate;
EXAMPLE 1 (METHOD 1A) 4-Methoxy-3-trifluoromethyl-phenylamine A suspension of <strong>[654-76-2]4-methoxy-3-trifluoromethyl-nitrobenzene</strong> (2.2 g) and iron powder (1.68 g) in ethanol (35 mL) and water (15 mL) is treated with a solution of concentrated hydrochloric acid (0.42 mL) in ethanol (6 mL) and water (3 mL) and the mixture is heated to reflux for approximately 1 hour. The mixture is then cooled, filtered, and concentrated under reduced pressure. The resulting oil is dissolved in ethyl acetate and extracted three times with 5% aqueous hydrochloric acid. The pooled acidic extracts are then cooled in an ice bath and basified with solid potassium carbonate, then extracted with ethyl acetate. These organic extracts are washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, concentrated under reduced pressure, then passed through a short column of silica gel (ethyl acetate is used as the eluant) to provide the desired compound as an amber oil.
With sodium hydroxide; tetraethylammonium chloride; In methanol; water;
(A) 45 g of sodium hydroxide and 10 g of tetraethylammonium chloride in 200 g of methanol are initially introduced, 112.5 g of 2-chloro-5-nitro-benzotrifluoride are added dropwise at 25 to 30 C. and the mixture is then stirred at 30 C. for a further 5 hours. The mixture is then poured into 250 ml of water and extracted with methylene chloride. After evaporating off the solvent, the compound is recrystallized from isopropanol. 67 g of 2-methoxy-5-nitro-benzotrifluoride with a melting point of 70 to 74 C. are obtained.
4-(3-((1-(4-chloro-2-fluorophenyl)-2-(5-methoxy-6-(trifluoromethyl)indolin-1-yl)-2-oxoethyl)amino)-5-methoxyphenoxy)butanoic acid hydrochloride[ No CAS ]
4-(3-((1-(4-chloro-2-methoxyphenyl)-2-(5-methoxy-6-(trifluoromethyl)indolin-1-yl)-2-oxoethyl)amino)-5-methoxyphenoxy)butanoic acid hydrochloride[ No CAS ]
2-(2-(2-((tert-butyldimethylsilyl)oxy)ethoxy)-4-chlorophenyl)-2-((3-methoxy-5-(1H-1,2,4-triazol-1-yl)phenyl)amino)-1-(5-methoxy-6-(trifluoromethyl)indolin-1-yl)ethanone[ No CAS ]
2-(4-chloro-2-(2-hydroxyethoxy)phenyl)-2-((3-methoxy-5-(1H-1,2,4-triazol-1-yl)phenyl)amino)-1-(5-methoxy-6-(trifluoromethyl)indolin-1-yl)ethanone[ No CAS ]
2-(4-chloro-2-(2-hydroxyethoxy)phenyl)-2-((3-methoxy-5-(1H-1,2,4-triazol-1-yl)phenyl)amino)-1-(5-methoxy-6-(trifluoromethyl)indolin-1-yl)ethanone[ No CAS ]
2-(4-chloro-2-(2-hydroxyethoxy)phenyl)-2-((3-methoxy-5-(1H-1,2,4-triazol-1-yl)phenyl)amino)-1-(5-methoxy-6-(trifluoromethyl)indolin-1-yl)ethanone[ No CAS ]
tert-butyl 4-(5-chloro-2-(1-((3-methoxy-5-(1H-1,2,4-triazol-1-yl)phenyl)amino)-2-(5-methoxy-6-(trifluoromethyl)indolin-1-yl)-2-oxoethyl)phenoxy)butanoate[ No CAS ]
4-(5-chloro-2-(1-((3-methoxy-5-(1H-1,2,4-triazol-1-yl)phenyl)amino)-2-(5-methoxy-6-(thfluoromethyl)indolin-1-yl)-2-oxoethyl)phenoxy)butanoic acid[ No CAS ]
4-(5-chloro-2-(1-((3-methoxy-5-(1H-1,2,4-triazol-1-yl)phenyl)amino)-2-(5-methoxy-6-(thfluoromethyl)indolin-1-yl)-2-oxoethyl)phenoxy)butanoic acid[ No CAS ]
4-(5-chloro-2-(1-((3-methoxy-5-(1H-1,2,4-triazol-1-yl)phenyl)amino)-2-(5-methoxy-6-(thfluoromethyl)indolin-1-yl)-2-oxoethyl)phenoxy)butanoic acid[ No CAS ]
2-(4-fluoro-2-(2-hydroxyethoxy)phenyl)-2-((3-methoxy-5-(1H-1,2,4-triazol-1-yl)phenyl)amino)-1-(5-methoxy-6-(trifluoromethyl)indolin-1-yl)ethanone[ No CAS ]
2-(4-fluoro-2-(2-hydroxyethoxy)phenyl)-2-((3-methoxy-5-(1H-1,2,4-triazol-1-yl)phenyl)amino)-1-(5-methoxy-6-(trifluoromethyl)indolin-1-yl)ethanone[ No CAS ]
2-(4-fluoro-2-(2-hydroxyethoxy)phenyl)-2-((3-methoxy-5-(1H-1,2,4-triazol-1-yl)phenyl)amino)-1-(5-methoxy-6-(trifluoromethyl)indolin-1-yl)ethanone[ No CAS ]
2-(2-(2-((tert-butyldimethylsilyl)oxy)ethoxy)-4-fluorophenyl)-2-((3-methoxy-5-(1H-1,2,4-triazol-1-yl)phenyl)amino)-1-(5-methoxy-6-(trifluoromethyl)indolin-1-yl)ethanone[ No CAS ]
tert-butyl 4-(5-chloro-2-(1-((3-methoxy-5-(methylsulfonyl)phenyl)amino)-2-(5-methoxy-6-(trifluoromethyl)indolin-1-yl)-2-oxoethyl)phenoxy)butanoate[ No CAS ]
2-(2-(2-((tert-butyldimethylsilyl)oxy)ethoxy)-4-fluorophenyl)-2-((3-methoxy-5-(methylsulfonyl)phenyl)amino)-1-(5-methoxy-6-(trifluoromethyl)indolin-1-yl)ethanone[ No CAS ]
2-(2-(2-((tert-butyldimethylsilyl)oxy)ethoxy)-4-chlorophenyl)-2-((3-methoxy-5-(methylsulfonyl)phenyl)amino)-1-(5-methoxy-6-(trifluoromethyl)indolin-1-yl)ethanone[ No CAS ]
4-methoxy-N-(4-methoxyphenyl)-3-(trifluoromethyl)aniline[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
44%
With triethylphosphine; In m-xylene; at 120℃; for 16h;Inert atmosphere; Schlenk technique; Sealed tube;
General procedure: A glass culture tube containing a magnetic stir bar was charged with a nitroarene substrate and boronic acid, then fitted with a PTFE-lined silicone septum within a phenolic screw-thread open-top cap after wrapping the reaction tube thread once with Teflon tape. The vessel was evacuated and backfilled with nitrogen on a Schlenk line. Dry m-xylene (2 mL, 0.5 M) was added via syringe, followed by triethylphosphine (0.44 mL, 3 equivalents) and the reaction mixturewas heated 120 C with stirring. Upon completion, the reaction mixture was cooled to ambient temperature then diluted with 10 mL of distilled water. With the aid of ethyl acetate (ca. 3 x 10 mL), the reaction mixture was transferred to a separatory funnel. After mixing and separating the phases, the organic layer was washed with 10 mL of a 1M NaOH aqueous solution, and 10 mL of brine. Each aqueous phase was back-extracted with one 10 mL portion of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated by rotary evaporation. The crude residues were purified via column chromatography to yield pure coupling products. Columns were primarily slurry packed with hexanes and mobile phase polarity was increased gradually to the mixture indicated. Note: hexanes = Hex, dichloromethane = DCM, ethyl acetate = EA.
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