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CAS No. : | 443-75-4 | MDL No. : | MFCD01074503 |
Formula : | C10H8FNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OOEZASHYQRURRT-UHFFFAOYSA-N |
M.W : | 193.17 | Pubchem ID : | 2774507 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.1 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 49.8 |
TPSA : | 53.09 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.41 cm/s |
Log Po/w (iLOGP) : | 1.18 |
Log Po/w (XLOGP3) : | 1.51 |
Log Po/w (WLOGP) : | 2.35 |
Log Po/w (MLOGP) : | 1.53 |
Log Po/w (SILICOS-IT) : | 2.62 |
Consensus Log Po/w : | 1.84 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.85 |
Log S (ESOL) : | -2.33 |
Solubility : | 0.898 mg/ml ; 0.00465 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.23 |
Solubility : | 1.13 mg/ml ; 0.00585 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.34 |
Solubility : | 0.0875 mg/ml ; 0.000453 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.72 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
With dihydrogen peroxide; horseradish peroxidase |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide In methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: nBuLi / tetrahydrofuran / 0 °C 1.2: ZnCl2 2.1: aq. NaOH / methanol | ||
Multi-step reaction with 2 steps 1.1: eschenmoser's salt; acetic acid / acetonitrile / 4 h / 20 °C 1.2: 18 h / 20 °C 1.3: 4 h / 70 °C 2.1: potassium hydroxide / water; methanol / 2 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | 3.b Example 3(b) Example 3(b) 6-Fluoroindole-3-acetic acid (SR043) Off-white needles, yield 30%, m.p. 161-163°C (lit. 165°C); m/z 193 (M+), 148 (M+ - CO2H), 101; δH/ppm (CD3COCD3): 7.61-6.43 (4H, m, ArH), 3.73 (2H, s, ArCH2); found C: 62.08%, H: 4.18%, N: 7.22% (calculated C: 62.18%, H: 4.17%, N: 7.25%). | |
30% | 3.b 6-Fluoroindole-3-acetic acid (SR043) Example 3(b) 6-Fluoroindole-3-acetic acid (SR043) Off-white needles, yield 30%, m.p. 161-163° C. (lit. 165° C.); m/z 193 (M+), 148 (M+-CO2H), 101; δH/ppm (CD3COCD3): 7.61-6.43 (4H, m, ArH), 3.73 (2H, s, ArCH2); found C, 62.08%, H: 4.18%, N, 7.22% (calculated C, 62.18%, H, 4.17%, N, 7.25%). | |
30% | 3.b 6-Fluoroindole-3-acetic acid (SR043) Example 3(b) 6-Fluoroindole-3-acetic acid (SR043) Off-white needles, yield 30%, m.p. 161-163° C. (lit. 165° C.); m/z 193 (M+), 148 (M+-CO2H), 101; δH/ppm (CD3COCD3): 7.61-6.43 (4H, m, ArH), 3.73 (2H, s, ArCH2); found C: 62.08%, H: 4.18%, N: 7.22% (calculated C: 62.18%, H: 4.17%, N: 7.25%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2-(6-fluoro-1H-indol-3-yl)acetic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 1h; Combinatorial reaction / High throughput screening (HTS); Stage #2: 1-(4-(dimethylamino)-4-phenylpiperidin-1-yl)-3-methyl-2-(methylamino)butan-1-one trihydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 12h; Combinatorial reaction / High throughput screening (HTS); | A solution of the indole carboxylic acid derivative ACI (150 μmol) in 1.6 ml dichloromethane was prepared at room temperature and a solution of carbonyldiimidazole (160 μmol) in 1 ml dichloromethane was added. The reaction mixture was shaken for 1 hour at room temperature and then a solution of the corresponding amine AA (100 μmol) in a mixture of 500 μmol N-ethyl-diisopropylamine and 0.5 ml dichloromethane was added. The reaction mixture was shaken for 12 hours at room temperature. The solvent was then removed under vacuum in a vacuum centrifuge (GeneVac). The final purification was performed by HPLC-MS. The final analysis was performed by LC-MS. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 8 h / 20 °C 2: trichlorophosphate / acetonitrile / 1.5 h / Inert atmosphere; Reflux 3: sodium tetrahydroborate / methanol / 8 h / 0 - 20 °C 4: formic acid / acetonitrile / 2 h / 25 - 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 8 h / 20 °C 2: trichlorophosphate / acetonitrile / 1.5 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 8 h / 20 °C 2: trichlorophosphate / acetonitrile / 1.5 h / Inert atmosphere; Reflux 3: sodium tetrahydroborate / methanol / 8 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With dmap; triethylamine; dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: dicyclohexyl-carbodiimide; dmap; triethylamine / tetrahydrofuran / 12 h / 0 - 20 °C 2: C70H68Au2Cl2F12N6O2; silver trifluoromethanesulfonate / toluene / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | Stage #1: 2-(6-fluoro-1H-indol-3-yl)acetic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N,N-dimethyl-formamide In ethyl acetate at 23℃; for 1h; Inert atmosphere; Stage #2: 4,6-dimethyl-2-(piperazin-1-yl)pyrimidine In ethyl acetate at 50℃; for 3h; Inert atmosphere; | General procedure for the coupling reactions to obtain compounds 5-8 and 13-25. General procedure: Toa suspension of indole acid and EDC.HCl were added EtOAc and two drops of DMF, and themixture was stirred for 1 h at 23°C followed by the addition of compound 4. The reaction washeated at 50°C for 3 h, and solvents were evaporated to dryness under high vacuum. Waterwas added, sonicated, and filtered. The filter cake was washed with hexane/EtOAc and furtherpurified by crystallization from MeOH/EtOH/Et2O/EtOAc. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | Stage #1: 2-(6-fluoro-1H-indol-3-yl)acetic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.75h; Stage #2: 4-(3-aminopropyl)-1-(triphenylmethyl)-imidazole With triethylamine In N,N-dimethyl-formamide at 20℃; for 16h; | |
56% | Stage #1: 2-(6-fluoro-1H-indol-3-yl)acetic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Stage #2: 4-(3-aminopropyl)-1-(triphenylmethyl)-imidazole With triethylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere; | 1.1D Synthesis of 2-(6-fluoro-1H-indol-3-yl)-N-(3-(1-trityl-1H-imidazol-4-yl)propyl)acetamide (I) To a solution of 2-(6-fluoro-1 H-indol-3-yl)acetic acid (H) (1.00 g, 5.18 mmol) in DMF (50 mL)was added EDCHCI (1.50 g, 7.77 mmol) and HOBtH20 (1.19 g, 7.77 mmol). The resulting mixture was stirred at room temperature for 1 h. A solution of the amine 7 (1.90 g, 5.18 mmol) and TEA (2.80 mL) were added and the reaction was stirred for 16 hours at room temperature. The mixture was partitioned with EtOAc (120 mL) and iN NaHSO4 (1 00 mL). The layers were separated and the EtOAc solution was washed with water (150 mL), sat. NaHCO3 (150 mL) and brine (150 mL). The EtOAc layer was dried (Na2SO4), filtered and concentrated. Trituration of the solid with hot ACN and filtration afforded 1.58 g (56% yield) of pure amide I: 1H NMR (400 MHz, DMSO-d6) ö 10.88 (bs, 1 H), 7.89 (t, J = 5.48 Hz, 1 H), 7.45 (dd, J = 8.69, 5.53 Hz, 1 H),7.37-7.23 (complex m, 9H), 7.19 (d, J= 1.20 Hz, 1H), 7.11 (d, J= 2.36 Hz, 1H), 7.06-7.01 (m, 7H), 6.73 (ddd, J = 11.04, 9.73, 2.33 Hz, 1 H), 6.53 (bs, 1 H), 3.40 (s, 2H), 2.98(apparent q, J = 6.71 Hz, 2H), 2.35 (t, J = 7.44 Hz, 2H), 1.58 (quint., J = 7.19 Hz, 2H).LCMS (50-95% acetonitrile in 0.05% TEA over 10 minutes) retention time = 4.38 mm,ESI m/z = 543, [M+H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | Stage #1: 2-(6-fluoro-1H-indol-3-yl)acetic acid; N,O-dimethylhydroxylamine*hydrochloride With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In dichloromethane; ethyl acetate at 20℃; Inert atmosphere; Stage #2: di-<i>tert</i>-butyl dicarbonate With dmap In dichloromethane at 20℃; for 2h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine / dichloromethane; ethyl acetate / 20 °C / Inert atmosphere 1.2: 2 h / 20 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; n-heptane / 2 h / -65 °C / Inert atmosphere 2.2: -65 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine / dichloromethane; ethyl acetate / 20 °C / Inert atmosphere 1.2: 2 h / 20 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; n-heptane / 2 h / -65 °C / Inert atmosphere 2.2: -65 °C / Inert atmosphere 3.1: ammonium acetate; sodium cyanoborohydride / methanol / 12 h / 70 °C / Inert atmosphere 3.2: 2 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With copper(II) acetate monohydrate In acetonitrile at 115℃; for 2h; Sealed tube; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With copper(II) acetate monohydrate In acetonitrile at 115℃; for 2h; Sealed tube; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(II) acetate monohydrate In acetonitrile at 115℃; for 2h; Sealed tube; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With copper(II) acetate monohydrate In acetonitrile at 115℃; for 2h; Sealed tube; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2-(6-fluoro-1H-indol-3-yl)acetic acid With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: triisopropylsilyl chloride In N,N-dimethyl-formamide at 0℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide In methanol; water at 100℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 1 h / 0 °C 2.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 40 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 1 h / 0 °C 2.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 40 °C 3.1: disodium hydrogenphosphate; Selectfluor; water; C69H48O6 / toluene / 24 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2-(6-fluoro-1H-indol-3-yl)acetic acid; 5-fluoro-N1-methylbenzene-1,2-diamine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Stage #2: With acetic acid In toluene at 150℃; Microwave irradiation; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | Stage #1: 2-(6-fluoro-1H-indol-3-yl)acetic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere; Stage #2: Spermine In N,N-dimethyl-formamide at 20℃; for 72h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride; triethylamine In N,N-dimethyl-formamide Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sulfuric acid / Reflux 2.1: sodium hydride / acetonitrile / 0.5 h / 20 °C 2.2: 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: sulfuric acid / Reflux 2.1: sodium hydride / acetonitrile / 0.5 h / 20 °C 2.2: 20 °C 3.1: sodium hydride / Reflux 4.1: ethanol; potassium hydroxide / 20 °C 4.2: 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sulfuric acid / Reflux 2.1: sodium hydride / acetonitrile / 0.5 h / 20 °C 2.2: 20 °C 3.1: sodium hydride / Reflux 4.1: ethanol; potassium hydroxide / 20 °C 4.2: 20 °C 5.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sulfuric acid / Reflux 2.1: sodium hydride / acetonitrile / 0.5 h / 20 °C 2.2: 20 °C 3.1: sodium hydride / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sulfuric acid / Reflux 2.1: sodium hydride / acetonitrile / 0.5 h / 20 °C 2.2: 20 °C 3.1: sodium hydride / Reflux 4.1: ethanol; potassium hydroxide / 20 °C 4.2: 20 °C 5.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 20 °C 6.1: triethylamine / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sulfuric acid / Reflux 2.1: sodium hydride / acetonitrile / 0.5 h / 20 °C 2.2: 20 °C 3.1: sodium hydride / Reflux 4.1: ethanol; potassium hydroxide / 20 °C 4.2: 20 °C 5.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 20 °C 6.1: triethylamine / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sulfuric acid / Reflux 2.1: sodium hydride / acetonitrile / 0.5 h / 20 °C 2.2: 20 °C 3.1: sodium hydride / Reflux 4.1: ethanol; potassium hydroxide / 20 °C 4.2: 20 °C 5.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 20 °C 6.1: triethylamine / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sulfuric acid / Reflux 2.1: sodium hydride / acetonitrile / 0.5 h / 20 °C 2.2: 20 °C 3.1: sodium hydride / Reflux 4.1: ethanol; potassium hydroxide / 20 °C 4.2: 20 °C 5.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 20 °C 6.1: triethylamine / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sulfuric acid / Reflux 2.1: sodium hydride / acetonitrile / 0.5 h / 20 °C 2.2: 20 °C 3.1: sodium hydride / Reflux 4.1: ethanol; potassium hydroxide / 20 °C 4.2: 20 °C 5.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 20 °C 6.1: triethylamine / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sulfuric acid / Reflux 2.1: sodium hydride / acetonitrile / 0.5 h / 20 °C 2.2: 20 °C 3.1: sodium hydride / Reflux 4.1: ethanol; potassium hydroxide / 20 °C 4.2: 20 °C 5.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 20 °C 6.1: triethylamine / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.65% | With sulfuric acid Reflux; | 41.2 (2) Preparation of 6-fluoro-indole-3-acetic acid methyl ester: Add 6-fluoro-3-indole acetic acid (3.86g, 20mmol) and anhydrous methanol (50mL) into a 100mL three-necked round bottom flask, add 3 drops of concentrated sulfuric acid, and heat to reflux for 6-10 hours. After the reaction, the solvent was concentrated and 100 mL of water was added, extracted with ethyl acetate (3×60 mL), the organic phases were combined, dried over anhydrous sodium sulfate, and the solvent was spin-dried to obtain 3.96 g of a light yellow solid with a yield of 95.65%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.75 h / 20 °C 1.2: 16 h / 20 °C 2.1: Lawessons reagent / tetrahydrofuran / Reflux 3.1: silver benzoate; acetic acid / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.75 h / 20 °C 1.2: 16 h / 20 °C 2.1: Lawessons reagent / tetrahydrofuran / Reflux 3.1: silver benzoate; acetic acid / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.75 h / 20 °C 1.2: 16 h / 20 °C 2.1: Lawessons reagent / tetrahydrofuran / Reflux 3.1: silver benzoate; acetic acid / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.75 h / 20 °C 1.2: 16 h / 20 °C 2.1: Lawessons reagent / tetrahydrofuran / Reflux 3.1: silver benzoate; acetic acid / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.75 h / 20 °C 1.2: 16 h / 20 °C 2.1: Lawessons reagent / tetrahydrofuran / Reflux 3.1: silver benzoate; acetic acid / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.75 h / 20 °C 1.2: 16 h / 20 °C 2.1: Lawessons reagent / tetrahydrofuran / Reflux 3.1: silver benzoate; acetic acid / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.75 h / 20 °C 1.2: 16 h / 20 °C 2.1: Lawessons reagent / tetrahydrofuran / Reflux 3.1: silver benzoate; acetic acid / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.75 h / 20 °C 1.2: 16 h / 20 °C 2.1: Lawessons reagent / tetrahydrofuran / Reflux 3.1: silver benzoate; acetic acid / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.75 h / 20 °C 1.2: 16 h / 20 °C 2.1: Lawessons reagent / tetrahydrofuran / Reflux 3.1: silver benzoate; acetic acid / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.75 h / 20 °C 1.2: 16 h / 20 °C 2.1: Lawessons reagent / tetrahydrofuran / Reflux 3.1: silver benzoate; acetic acid / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.75 h / 20 °C 1.2: 16 h / 20 °C 2.1: Lawessons reagent / tetrahydrofuran / Reflux 3.1: silver benzoate; acetic acid / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.75 h / 20 °C 1.2: 16 h / 20 °C 2.1: Lawessons reagent / tetrahydrofuran / Reflux 3.1: silver benzoate; acetic acid / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.75 h / 20 °C 1.2: 16 h / 20 °C 2.1: Lawessons reagent / tetrahydrofuran / Reflux 3.1: silver benzoate; acetic acid / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.5 h / 20 °C 1.2: 16 h / 20 °C 2.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 1.5 h / 20 °C 3.1: silver benzoate; acetic acid; triethylamine / dichloromethane / 90 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.75 h / 20 °C 1.2: 16 h / 20 °C 2.1: Lawessons reagent / tetrahydrofuran / Reflux 3.1: silver benzoate; acetic acid; triethylamine / dichloromethane / 90 h / 20 °C | ||
Multi-step reaction with 3 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.5 h / 20 °C 1.2: 16 h / 20 °C 2.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 1.5 h / 20 °C 3.1: silver benzoate; acetic acid; triethylamine / dichloromethane / 90 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.5 h / 20 °C 1.2: 16 h / 20 °C 2.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 1.5 h / 20 °C 3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 70 °C 4.1: sodium hydroxide / ethanol / 3 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.5 h / 20 °C 1.2: 16 h / 20 °C 2.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 1.5 h / 20 °C 3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 70 °C 4.1: sodium hydroxide / ethanol / 3 h / 50 °C 5.1: acetic acid; dihydrogen peroxide / dichloromethane / 2 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.5 h / 20 °C 1.2: 16 h / 20 °C 2.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 1.5 h / 20 °C 3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.75 h / 20 °C 1.2: 16 h / 20 °C 2.1: Lawessons reagent / tetrahydrofuran / Reflux 3.1: silver benzoate; acetic acid / dichloromethane / 20 °C 4.1: hydrogenchloride / ethanol; water / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.75 h / 20 °C 1.2: 16 h / 20 °C 2.1: Lawessons reagent / tetrahydrofuran / Reflux 3.1: silver benzoate; acetic acid / dichloromethane / 20 °C 4.1: hydrogenchloride / ethanol; water / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.75 h / 20 °C 1.2: 16 h / 20 °C 2.1: Lawessons reagent / tetrahydrofuran / Reflux 3.1: silver benzoate; acetic acid / dichloromethane / 20 °C 4.1: hydrogenchloride / ethanol; water / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.75 h / 20 °C 1.2: 16 h / 20 °C 2.1: Lawessons reagent / tetrahydrofuran / Reflux 3.1: silver benzoate; acetic acid / dichloromethane / 20 °C 4.1: hydrogenchloride / ethanol; water / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.75 h / 20 °C 1.2: 16 h / 20 °C 2.1: Lawessons reagent / tetrahydrofuran / Reflux 3.1: silver benzoate; acetic acid / dichloromethane / 20 °C 4.1: hydrogenchloride / ethanol; water / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.75 h / 20 °C 1.2: 16 h / 20 °C 2.1: Lawessons reagent / tetrahydrofuran / Reflux 3.1: silver benzoate; acetic acid / dichloromethane / 20 °C 4.1: hydrogenchloride / ethanol; water / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.75 h / 20 °C 1.2: 16 h / 20 °C 2.1: Lawessons reagent / tetrahydrofuran / Reflux 3.1: silver benzoate; acetic acid / dichloromethane / 20 °C 4.1: hydrogenchloride / ethanol; water / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.75 h / 20 °C 1.2: 16 h / 20 °C 2.1: Lawessons reagent / tetrahydrofuran / Reflux 3.1: silver benzoate; acetic acid / dichloromethane / 20 °C 4.1: hydrogenchloride / ethanol; water / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.75 h / 20 °C 1.2: 16 h / 20 °C 2.1: Lawessons reagent / tetrahydrofuran / Reflux 3.1: silver benzoate; acetic acid / dichloromethane / 20 °C 4.1: hydrogenchloride / ethanol; water / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.75 h / 20 °C 1.2: 16 h / 20 °C 2.1: Lawessons reagent / tetrahydrofuran / Reflux 3.1: silver benzoate; acetic acid / dichloromethane / 20 °C 4.1: hydrogenchloride / ethanol; water / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.75 h / 20 °C 1.2: 16 h / 20 °C 2.1: Lawessons reagent / tetrahydrofuran / Reflux 3.1: silver benzoate; acetic acid / dichloromethane / 20 °C 4.1: hydrogenchloride / ethanol; water / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.75 h / 20 °C 1.2: 16 h / 20 °C 2.1: Lawessons reagent / tetrahydrofuran / Reflux 3.1: silver benzoate; acetic acid / dichloromethane / 20 °C 4.1: hydrogenchloride / ethanol; water / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.75 h / 20 °C 1.2: 16 h / 20 °C 2.1: Lawessons reagent / tetrahydrofuran / Reflux 3.1: silver benzoate; acetic acid / dichloromethane / 20 °C 4.1: hydrogenchloride / ethanol; water / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.5 h / 20 °C 1.2: 16 h / 20 °C 2.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 1.5 h / 20 °C 3.1: silver benzoate; acetic acid; triethylamine / dichloromethane / 90 h / 20 °C 4.1: hydrogenchloride / ethanol; water / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.5 h / 20 °C 1.2: 16 h / 20 °C 2.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 1.5 h / 20 °C 3.1: silver benzoate; acetic acid; triethylamine / dichloromethane / 90 h / 20 °C 4.1: hydrogenchloride / ethanol; water / 70 °C | ||
Multi-step reaction with 4 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.75 h / 20 °C 1.2: 16 h / 20 °C 2.1: Lawessons reagent / tetrahydrofuran / Reflux 3.1: silver benzoate; acetic acid; triethylamine / dichloromethane / 90 h / 20 °C 4.1: hydrogenchloride / ethanol; water / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.5 h / 20 °C 1.2: 16 h / 20 °C 2.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 1.5 h / 20 °C 3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 70 °C 4.1: sodium hydroxide / ethanol / 3 h / 50 °C 5.1: acetic acid; dihydrogen peroxide / dichloromethane / 2 h / 0 - 20 °C 6.1: hydrogenchloride / ethanol; water / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.75 h / 20 °C 1.2: 16 h / 20 °C 2.1: Lawessons reagent / tetrahydrofuran / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.5 h / 20 °C 1.2: 16 h / 20 °C 2.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 1.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | Stage #1: 2-(6-fluoro-1H-indol-3-yl)acetic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: t-butoxycarbonylhydrazine With triethylamine In N,N-dimethyl-formamide at 20℃; for 16h; |
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