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CAS No. : | 144291-47-4 | MDL No. : | MFCD06801752 |
Formula : | C15H12O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MNUSHZDUHWBMSZ-UHFFFAOYSA-N |
M.W : | 240.25 | Pubchem ID : | 4325150 |
Synonyms : |
|
Num. heavy atoms : | 18 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.07 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 68.55 |
TPSA : | 43.37 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.3 cm/s |
Log Po/w (iLOGP) : | 2.29 |
Log Po/w (XLOGP3) : | 3.47 |
Log Po/w (WLOGP) : | 2.95 |
Log Po/w (MLOGP) : | 2.71 |
Log Po/w (SILICOS-IT) : | 3.6 |
Consensus Log Po/w : | 3.0 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.75 |
Solubility : | 0.0432 mg/ml ; 0.00018 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.06 |
Solubility : | 0.0208 mg/ml ; 0.0000865 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -4.95 |
Solubility : | 0.00272 mg/ml ; 0.0000113 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.96 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,2-dimethoxyethane; water; toluene at 85℃; Inert atmosphere; | |
90% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane; water at 95℃; for 4h; Inert atmosphere; | 1.2 1-2. Preparation of Methyl-4′-formylbiphenyl-2-carboxylate 1-2. Preparation of Methyl-4'-formylbiphenyl-2-carboxylate Methyl-2-bromobenzoate (2.0 g, 9.30 mmol) obtained in Example 1-1 and 4-formylphenylboronic acid (1.46 g, 9.76 mmol) were added to a stirring solution of 1,4-dioxane (20 mL) and water (4 mL). The mixture was degassed with argon for 15 minutes, and PdCl2 (dppf)CH2Cl2 (0.379 g, 0.46 mmol) and Na2CO3 (2.38 g, 23.25 mmol) were added thereto. The mixture was degassed again and stirred at 95° C. for 4 hours. The mixture was cooled at room temperature, diluted with ethyl acetate, and filtered through a celite bed. The filtrate was washed with brine, and the organic solvent layer was collected, concentrated, and purified by silica gel column chromatography (n-Hexane:EtOAc=1:4), yielding methyl-4'-formylbiphenyl-2-carboxylate as a while solid phase (2.0 g, 90.0% yield). |
71% | With sodium carbonate In tetrahydrofuran at 60℃; for 4h; |
66% | With sodium carbonate In tetrahydrofuran; water at 60℃; for 10h; | |
58% | With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 75℃; for 5h; Inert atmosphere; | |
With potassium phosphate In DMF (N,N-dimethyl-formamide) at 75℃; for 5h; | 7 2-(4-formylphenyl)benzoic acid methyl ester To a solution of 4-formylphenylboric acid (6.7 g) in N,N-dimethylformamide (100 ml) were added 2-bromobenzoic acid methyl ester (6.5 g), tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] (1.0 g) and tripotassium phosphate (23 g). The reaction mixture was stirred for 5 hours at 75°C. The reaction mixture was filtrated and concentrated. To the residue were added 1N hydrochloric acid and ethyl acetate, and the mixture was concentrated. The residue was purified by column chromatography on silica gel (hexane: ethyl acetate=9: 1) to give the title compound (4.1 g) having the following physical data. TLC:Rf 0.50(hexane:ethyl acetate=2:1); NMR (CDCl3): δ.10.07 (s, 1H), 7.96-7.89 (m, 3H), 7.63-7.34 (m, 5H), 3.66 (s, 3H). | |
With potassium phosphate In DMF (N,N-dimethyl-formamide) at 75℃; for 5h; | 7 2-(4-formylphenyl)benzoic acid methyl ester To a solution of 4-formylphenylboric acid (6.7 g) in N,N-dimethylformamide (100 ml) were added 2-bromobenzoic acid methyl ester (6.5 g), tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] (1.0 g) and tripotassium phosphate (23 g). The reaction mixture was stirred for 5 hours at 75°C. The reaction mixture was filtrated and concentrated. To the residue were added 1N hydrochloric acid and ethyl acetate, and the mixture was concentrated. The residue was purified by column chromatography on silica gel (hexane : ethyl acetate=9: 1) to give the title compound (4.1 g) having the following physical data. TLC:Rf 0.50(hexane:ethyl acetate=2:1); NMR (CDCl3): δ.10.07 (s, 1H), 7.96-7.89 (m, 3H), 7.63-7.34 (m, 5H), 3.66 (s, 3H). | |
With potassium phosphate In DMF (N,N-dimethyl-formamide) at 75℃; for 5h; | 1 Under atmosphere of argon, to a solution of 4-formylphenylboric acid (6.7g) in N,N-dimethylformamide (100ml), 2-bromobenzoic acid methyl ester(6.5g), tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] (1.0g) and tripotassium phosphate (23g) were added and the mixture was stirred for 5 hours at 75°C. The reaction mixture was filtered and the filtrate was concentrateded. 1N Hydrochloric acid was added to the residue and the mixture was extracted by ethyl acetate. The extract was washed with saturated aqueous solution of sodium hydrogen carbonate and brine sequentially, dried over anhydrous sodium sulfate, concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Hexane : Ethyl acetate = 9 : 1) to give the title compound (4.lg) having the following physical data. TLC ; Rf 0.50 (Hexane : Ethyl acetate = 2 : 1); NMR (CDCl3) : δ 10.07 (s, 1H), 7.96-7.89 (m, 3H), 7.63-7.34 (m, 5H), 3.66 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With sodium tris(acetoxy)borohydride; acetic acid In N,N-dimethyl-formamide at 20℃; for 4h; | |
With sodium tris(acetoxy)borohydride In DMF (N,N-dimethyl-formamide) at 20℃; for 2.5h; | 8 2-(4-(3-phenylpropylaminomethyl)phenyl)benzoic acid methyl ester To a solution of the compound prepared in reference example 7 (1.2 g) in acetic acid (4 ml)-N,N-dimethylformamide (36 ml) were added 3-phenylpropylamine (1 g) and sodium borotriacetoxyhydride (1.6 g). The reaction mixture was stirred for 2.5 hours at room temperature. To the reaction mixture were added a saturated aqueous solution of sodium bicarbonate and ethyl acetate and extracted. The extract was washed with a saturated aqueous solution of sodium bicarbonate and anhydrous sodium sulfate and concentrated to give the title compound (1.8 g) having the following physical data. TLC:Rf 0.59(dichloromethane:methanol=9:1). | |
With sodium tris(acetoxy)borohydride In DMF (N,N-dimethyl-formamide); acetic acid at 20℃; for 2.5h; | 8 2-(4-(3-phenylpropylaminomethyl)phenyl)benzoic acid methyl ester To a solution of the compound prepared in reference example 7 (1.2 g) in acetic acid (4 ml)-N,N-dimethylformamide (36 ml) were added 3-phenylpropylamine (1 g) and sodium borotriacetoxyhydride (1.6 g). The reaction mixture was stirred for 2.5 hours at room temperature. To the reaction mixture were added a saturated aqueous solution of sodium bicarbonate and ethyl acetate and extracted. The extract was washed with a saturated aqueous solution of sodium bicarbonate and anhydrous sodium sulfate and concentrated to give the title compound (1.8 g) having the following physical data. TLC:Rf 0.59(dichloromethane:methanol=9:1). |
With sodium tris(acetoxy)borohydride In DMF (N,N-dimethyl-formamide); acetic acid at 20℃; for 2.5h; | 2 To a solution of the compound prepared in Reference example 1 (1.2g) in a mixed solvent of acetic acid (4ml) and N,N-dimethylformamide (36ml), 3-phenylpropylamine (1g) and sodium triacetoxyborohydride (1.6g) were added sequentially and the mixture was stirred for 2.5 hours at room temperature. Saturated aqueous solution of sodium hydrogen carbonate was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous solution of sodium hydrogen carbonate and brine sequentially, dried over anhydrous sodium sulfate, concentrated under reduced pressure to give the title compound (1.8g) having the following physical data. TLC : Rf 0.59 (Dichloromethane : Methanol = 9 : 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
R.97.c Reference Example 97c Reference Example 97c 4-(2-Methoxycarbonyl-phenyl)-Benzaldehyde. Using essentially the same procedure used in reference example 97b except using methyl 2-iodo-benzoate as substrate in place of methyl 3-bromo-benzoate. MS (EI) m/z 240 (M)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2-nitropropane; sodium In ethanol at 70℃; for 4h; | 4 methyl 4'-formylbiphenyl-2-carboxylate 2-nitropropane (3.56g) was added to a solution that sodium (85mg) was added to ethanol (50mL) little by little. Further, the compound (8.40g) prepared in Example 3 in ethanol solution (10mL) was added and stirred for 4 hours at 70°C. The reaction mixture was concentrated and extracted with ethyl acetate after adding water. The extract was sequentially washed with 1 mol/L sodium hydroxide solution and saturated brine and dried by anhydrous sodium sulfate, and then concentrated. The titled compound (5.02g) having the following physical data was obtained by purifying the obtained residue by silica gel column chromatography (ethyl acetate:hexane= 1:5). TLC: Rf 0.50 (ethyl acetate:hexane=1:2); NMR (CDCl3) : δ 10.07 (s, 1H), 7.96-7.89 (m, 3H), 7.63-7.34 (m, 5H), 3.66 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | Stage #1: aniline; 4-(2-Methoxycarbonyl-phenyl)-Benzaldehyde With magnesium sulfate In chloroform Stage #2: With sodium tetrahydroborate In tetrahydrofuran; ethanol at 50℃; for 2h; | |
86% | With sodium cyanoborohydride; zinc(II) chloride In methanol at 20℃; for 4h; | 1.3 1-3. Preparation of methyl-4′-[(phenylamino)methyl]biphenyl-2-carboxylate 1-3. Preparation of methyl-4'-[(phenylamino)methyl]biphenyl-2-carboxylate A methanol solution (5 mL) in which sodium cyanoborohydride (4.0 ml (1M), 4.16 mmol) and zinc chloride (4.0 ml (0.5M), 2.08 mmol) were dissolved was slowly added at room temperature to a methanol solution (10 mL) in which methyl-4'-formylbiphenyl-2-carboxylate (1.0 g, 4.16 mmol) obtained in Example 1-2 and aniline (1.16 g, 12.48 mmol) were dissolved, and the mixture was stirred at room temperature for 4 hours. The mixture was concentrated under reduced pressure, diluted with ethyl acetate, and washed with brine and water. Then, the organic solvent layer was collected, dehydrated with anhydrous MgSO4, and filtered, and then the resulting organic solvent layer was concentrated by evaporation. The concentrate was purified by silica gel column chromatography (n-Hexane:EtOAc=4:1), yielding methyl-4'-[(phenylamino)methyl]biphenyl-2-carboxylate as a white solid phase (1.13 g, 86% yield). |
Stage #1: aniline; 4-(2-Methoxycarbonyl-phenyl)-Benzaldehyde In methanol at 20℃; for 4h; Stage #2: With sodium tetrahydroborate In methanol for 1.5h; | 8 methyl 4'-(anilinomethyl)biphenyl-2-carboxylate Example 8 methyl 4'-(anilinomethyl)biphenyl-2-carboxylate Phenylamine (56mg) was added to the compound (120mg) prepared in Example 4 in methanol solution (3mL) and stirred for 4 hours at room temperature. The reaction mixture was added to sodium borohydride(37mg) and stirred for 1.5 hours. To alkalinize, 5 mol/L sodium hydroxide solution was added to the concentrated reaction mixture and then extracted with ethyl acetate. The organic layer was washed with saturated sodium and dried by anhydrous sodium sulfate, and then concentrated to obtain the titled compound (124mg) having the following physical data by purifying the obtained residue by silica gel column chromatography(diethyl ether:hexane=1:2). TLC: Rf 0.42 (ethyl acetate:hexane =1:4); NMR (CDC13): δ 7.86-7.80 (m, 1H), 7.58-7.14 (m, 9H), 6.78-6.64 (m, 3H), 4.38 (s, 2H), 4.20-4.00 (br, 1H), 3.65 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | Stage #1: benzylamine; 4-(2-Methoxycarbonyl-phenyl)-Benzaldehyde With magnesium sulfate In chloroform Stage #2: With sodium tetrahydroborate In tetrahydrofuran; ethanol at 50℃; for 2h; | |
Stage #1: benzylamine; 4-(2-Methoxycarbonyl-phenyl)-Benzaldehyde In methanol at 20℃; for 4h; Stage #2: With sodium cyanoborohydride In methanol at 20℃; for 1h; | 5 methyl 4'-[(benzylamino)methyl]biphenyl-2-carboxylate Benzylamine(128mg) was added to the compound(120mg) prepared in Example 4 in methanol solution (3mL) and stirred for 4 hours at room temperature. Cyano sodium borohydride (62mg) was added to the reaction mixture and then acetic acid was dropped until pH.5.5 and stirred for 1 hour at room temperature. The reaction mixture was concentrated and alkalinized with 5mo1/L sodium hydroxide solution, and then extracted with ethyl acetate. The organic layer was washed with saturated brine and dried by anhydrous sodium sulfate, and then concentrated. The titled compound (94mg) having the following physical data was obtained by purifying the obtained residue by silica gel column chromatography (chloroform:hexane=30:1). TLC: Rf 0.51 (chloroform:methanol=9:1); NMR (CDCl3): δ 7.85-7.79 (m, 1H), 7.58-7.22 (m, 12H), 3.87 (s, 2H), 3.86 (s, 2H), 3.65 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium tetrahydroborate In methanol at 20℃; for 1h; | 10 methyl 4'-(hydroxymethyl)biphenyl-2-carboxylate Sodium borohydride (111mg) was added to the compound (400mg) prepared in Example 4 in methanol solution (10mL) and stirred for 1 hour at room temperature. The reaction mixture was concentrated and extracted with 1mol/L hydrochloric acid and ethyl acetate. The organic layer was washed with saturated sodium and dried by anhydrous sodium sulfate, and then concentrated to obtain the titled compound (400mg) having the following physical data. TLC: Rf 0.33 (ethyl acetate:hexane =1:1); NMR (CDCl3): δ 7.86-7.80 (m, 1H), 7.60-7.26 (m, 7H), 4.75 (s, 2H), 3.67 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With tetrabutylammomium bromide; palladium diacetate; sodium carbonate In 1,2-dimethoxyethane; water at 150℃; for 0.166667h; Microwave irradiation; | |
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; water at 20 - 80℃; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With isopropylmagnesium chloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at -40 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide; water / tetrahydrofuran / 80 °C 2: dipotassium peroxodisulfate; oxygen; silver nitrate / water; acetonitrile / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water; sodium hydroxide In tetrahydrofuran at 80℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: N,N-dimethylammonium chloride; 4-(2-Methoxycarbonyl-phenyl)-Benzaldehyde With sodium acetate; acetic acid In tetrahydrofuran for 0.0833333h; Cooling with ice; Stage #2: With sodium tris(acetoxy)borohydride In tetrahydrofuran at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: thionyl chloride / 4 h / 90 °C / Cooling with ice 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate / 1,4-dioxane; water / 4 h / 95 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium cyanoborohydride; zinc(II) chloride / methanol / 4 h / 20 °C 2: triethylamine / dichloromethane / 4 h / 20 °C / Cooling with ice | ||
Multi-step reaction with 2 steps 1.1: magnesium sulfate / chloroform 1.2: 2 h / 50 °C 2.1: triethylamine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium cyanoborohydride; zinc(II) chloride / methanol / 4 h / 20 °C 2: triethylamine / dichloromethane / 4 h / 20 °C / Cooling with ice 3: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 °C | ||
Multi-step reaction with 3 steps 1.1: magnesium sulfate / chloroform 1.2: 2 h / 50 °C 2.1: triethylamine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere 3.1: lithium hydroxide / water; tetrahydrofuran; methanol / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: sodium cyanoborohydride; zinc(II) chloride / methanol / 4 h / 20 °C 2.1: triethylamine / dichloromethane / 4 h / 20 °C / Cooling with ice 3.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 °C 4.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 20 °C 4.2: 4 h / 20 °C / Cooling with ice |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: acetic acid; sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: benzotriazol-1-ol / N,N-dimethyl-formamide / 16 h / 20 °C 2.2: PS-trisamine / 1.5 h 3.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 65 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: acetic acid; sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: benzotriazol-1-ol / N,N-dimethyl-formamide / 16 h / 20 °C 2.2: PS-trisamine / 1.5 h 3.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 65 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: acetic acid; sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: benzotriazol-1-ol / N,N-dimethyl-formamide / 16 h / 20 °C 2.2: PS-trisamine / 1.5 h 3.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 65 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: acetic acid; sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: benzotriazol-1-ol / N,N-dimethyl-formamide / 16 h / 20 °C 2.2: PS-trisamine / 1.5 h 3.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 65 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: acetic acid; sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: benzotriazol-1-ol / N,N-dimethyl-formamide / 16 h / 20 °C 2.2: PS-trisamine / 1.5 h 3.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 65 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: acetic acid; sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: benzotriazol-1-ol / N,N-dimethyl-formamide / 16 h / 20 °C 2.2: PS-trisamine / 1.5 h 3.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 65 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: acetic acid; sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: benzotriazol-1-ol / N,N-dimethyl-formamide / 16 h / 20 °C 2.2: PS-trisamine / 1.5 h 3.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 65 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: acetic acid; sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: benzotriazol-1-ol / N,N-dimethyl-formamide / 16 h / 20 °C 2.2: PS-trisamine / 1.5 h 3.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 65 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: acetic acid; sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: benzotriazol-1-ol / N,N-dimethyl-formamide / 16 h / 20 °C 2.2: PS-trisamine / 1.5 h 3.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 65 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: acetic acid; sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: benzotriazol-1-ol / N,N-dimethyl-formamide / 16 h / 20 °C 2.2: PS-trisamine / 1.5 h 3.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 65 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: acetic acid; sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: benzotriazol-1-ol / N,N-dimethyl-formamide / 16 h / 20 °C 2.2: PS-trisamine / 1.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: acetic acid; sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: benzotriazol-1-ol / N,N-dimethyl-formamide / 16 h / 20 °C 2.2: PS-trisamine / 1.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: acetic acid; sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: benzotriazol-1-ol / N,N-dimethyl-formamide / 16 h / 20 °C 2.2: PS-trisamine / 1.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: acetic acid; sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: benzotriazol-1-ol / N,N-dimethyl-formamide / 16 h / 20 °C 2.2: PS-trisamine / 1.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: acetic acid; sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: benzotriazol-1-ol / N,N-dimethyl-formamide / 16 h / 20 °C 2.2: PS-trisamine / 1.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: acetic acid; sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: benzotriazol-1-ol / N,N-dimethyl-formamide / 16 h / 20 °C 2.2: PS-trisamine / 1.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: acetic acid; sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: benzotriazol-1-ol / N,N-dimethyl-formamide / 16 h / 20 °C 2.2: PS-trisamine / 1.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: acetic acid; sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: benzotriazol-1-ol / N,N-dimethyl-formamide / 16 h / 20 °C 2.2: PS-trisamine / 1.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: acetic acid; sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: benzotriazol-1-ol / N,N-dimethyl-formamide / 16 h / 20 °C 2.2: PS-trisamine / 1.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: acetic acid; sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: benzotriazol-1-ol / N,N-dimethyl-formamide / 16 h / 20 °C 2.2: PS-trisamine / 1.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | Stage #1: 4-chloro-aniline; 4-(2-Methoxycarbonyl-phenyl)-Benzaldehyde With magnesium sulfate In chloroform Stage #2: With sodium tetrahydroborate In tetrahydrofuran; ethanol at 50℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | Stage #1: N-butylamine; 4-(2-Methoxycarbonyl-phenyl)-Benzaldehyde With magnesium sulfate In chloroform Stage #2: With sodium tetrahydroborate In tetrahydrofuran; ethanol at 50℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | Stage #1: 4-methoxy-aniline; 4-(2-Methoxycarbonyl-phenyl)-Benzaldehyde With magnesium sulfate In chloroform Stage #2: With sodium tetrahydroborate In tetrahydrofuran; ethanol at 50℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | Stage #1: 3-chloro-aniline; 4-(2-Methoxycarbonyl-phenyl)-Benzaldehyde With magnesium sulfate In chloroform Stage #2: With sodium tetrahydroborate In tetrahydrofuran; ethanol at 50℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | Stage #1: isopropylamine; 4-(2-Methoxycarbonyl-phenyl)-Benzaldehyde With magnesium sulfate In chloroform Stage #2: With sodium tetrahydroborate In tetrahydrofuran; ethanol at 50℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | Stage #1: cyclohexylamine; 4-(2-Methoxycarbonyl-phenyl)-Benzaldehyde With magnesium sulfate In chloroform Stage #2: With sodium tetrahydroborate In tetrahydrofuran; ethanol at 50℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | Stage #1: 4-phenoxyanilin; 4-(2-Methoxycarbonyl-phenyl)-Benzaldehyde With magnesium sulfate In chloroform Stage #2: With sodium tetrahydroborate In tetrahydrofuran; ethanol at 50℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | Stage #1: 4-(trifluoromethoxy)aniline; 4-(2-Methoxycarbonyl-phenyl)-Benzaldehyde With magnesium sulfate In chloroform Stage #2: With sodium tetrahydroborate In tetrahydrofuran; ethanol at 50℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | Stage #1: 4-fluoroaniline; 4-(2-Methoxycarbonyl-phenyl)-Benzaldehyde With magnesium sulfate In chloroform Stage #2: With sodium tetrahydroborate In tetrahydrofuran; ethanol at 50℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | Stage #1: 4-trifluoromethylphenylamine; 4-(2-Methoxycarbonyl-phenyl)-Benzaldehyde With magnesium sulfate In chloroform Stage #2: With sodium tetrahydroborate In tetrahydrofuran; ethanol at 50℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | Stage #1: meta-fluoroaniline; 4-(2-Methoxycarbonyl-phenyl)-Benzaldehyde With magnesium sulfate In chloroform Stage #2: With sodium tetrahydroborate In tetrahydrofuran; ethanol at 50℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | Stage #1: 4-(2-Methoxycarbonyl-phenyl)-Benzaldehyde; 3,4-difluoroaniline With magnesium sulfate In chloroform Stage #2: With sodium tetrahydroborate In tetrahydrofuran; ethanol at 50℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: magnesium sulfate / chloroform 1.2: 2 h / 50 °C 2.1: triethylamine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere 3.1: lithium hydroxide / water; tetrahydrofuran; methanol / 60 °C 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 48 h / 20 °C / Inert atmosphere |
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