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[ CAS No. 443-75-4 ] {[proInfo.proName]}

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Chemical Structure| 443-75-4
Chemical Structure| 443-75-4
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Product Details of [ 443-75-4 ]

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 :

Calculated chemistry of [ 443-75-4 ]

Physicochemical Properties

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

Pharmacokinetics

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

Lipophilicity

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

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.85

Water Solubility

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

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.72

Safety of [ 443-75-4 ]

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:

Application In Synthesis of [ 443-75-4 ]

* 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.

  • Downstream synthetic route of [ 443-75-4 ]

[ 443-75-4 ] Synthesis Path-Downstream   1~76

  • 1
  • [ 343-93-1 ]
  • [ 151-50-8 ]
  • [ 443-75-4 ]
YieldReaction ConditionsOperation in experiment
With dihydrogen peroxide; horseradish peroxidase
  • 3
  • (6-fluoro-1<i>H</i>-indol-3-yl)-acetic acid ethyl ester [ No CAS ]
  • [ 443-75-4 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide In methanol
  • 4
  • [ 399-51-9 ]
  • [ 443-75-4 ]
YieldReaction ConditionsOperation 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
YieldReaction ConditionsOperation 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%).
  • 6
  • [ 443-75-4 ]
  • 1-(4-(dimethylamino)-4-phenylpiperidin-1-yl)-3-methyl-2-(methylamino)butan-1-one trihydrochloride [ No CAS ]
  • [ 1181283-56-6 ]
YieldReaction ConditionsOperation 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.
  • 7
  • [ 443-75-4 ]
  • [ 1484-85-1 ]
  • C19H17FN2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 8h;
  • 8
  • [ 443-75-4 ]
  • 2,3-methylenedioxy-11-fluoro-5,8,14,14a-tetrahydro-6H-benzo[a]indolo[2,3-g]quinolizine [ No CAS ]
YieldReaction ConditionsOperation 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
  • 9
  • [ 443-75-4 ]
  • C19H15FN2O2 [ No CAS ]
YieldReaction ConditionsOperation 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
  • 10
  • [ 443-75-4 ]
  • C19H19FN2O2 [ No CAS ]
YieldReaction ConditionsOperation 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
  • 11
  • [ 128812-16-8 ]
  • [ 443-75-4 ]
  • 3-cyclohexyl-1-phenylprop-2-yn-1-yl 2-(6-fluoro-1H-indol-3-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With dmap; triethylamine; dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃; for 12h;
  • 12
  • [ 128812-16-8 ]
  • [ 443-75-4 ]
  • C25H24FNO2 [ No CAS ]
  • C25H24FNO2 [ No CAS ]
YieldReaction ConditionsOperation 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
  • 13
  • [ 443-75-4 ]
  • [ 22746-09-4 ]
  • 1-[4-(4,6-dimethylpyrimidin-2-yl)piperazin-1-yl]-2-(6-fluoro-1H-indol-3-yl)ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation 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.
  • 14
  • [ 443-75-4 ]
  • [ 195053-89-5 ]
  • 2-(6-fluoro-1H-indol-3-yl)-N-(3-(1-trityl-1H-imidazol-4-yl)propyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation 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].
  • 15
  • [ 443-75-4 ]
  • [ 24424-99-5 ]
  • [ 6638-79-5 ]
  • tert-butyl 6-fluoro-3-(2-(methoxy(methyl)amino)-2-oxoethyl)-1H-indole-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation 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;
  • 16
  • [ 443-75-4 ]
  • tert-butyl 6-fluoro-3-(2-(furan-2-yl)-2-oxoethyl)-1H-indole-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation 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
  • 17
  • [ 443-75-4 ]
  • tert-butyl 6-fluoro-3-(2-(furan-2-yl)-2-((4-methylphenyl)sulfonamido)ethyl)-1H-indole-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation 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
  • 18
  • [ 1006-94-6 ]
  • [ 443-75-4 ]
  • 6-fluoro-3-((5-methoxy-1H-indol-3-yl)methyl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With copper(II) acetate monohydrate In acetonitrile at 115℃; for 2h; Sealed tube; regioselective reaction;
  • 19
  • [ 16096-32-5 ]
  • [ 443-75-4 ]
  • 6-fluoro-3-((4-methyl-1H-indol-3-yl)methyl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With copper(II) acetate monohydrate In acetonitrile at 115℃; for 2h; Sealed tube; regioselective reaction;
  • 20
  • [ 52488-36-5 ]
  • [ 443-75-4 ]
  • 4-bromo-3-((6-fluoro-1H-indol-3-yl)methyl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper(II) acetate monohydrate In acetonitrile at 115℃; for 2h; Sealed tube; regioselective reaction;
  • 21
  • [ 1074-86-8 ]
  • [ 443-75-4 ]
  • 3-((6-fluoro-1H-indol-3-yl)methyl)-1H-indole-4-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With copper(II) acetate monohydrate In acetonitrile at 115℃; for 2h; Sealed tube; regioselective reaction;
  • 22
  • [ 443-75-4 ]
  • [ 13154-24-0 ]
  • C19H28FNO2Si [ No CAS ]
YieldReaction ConditionsOperation 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;
  • 23
  • [ 2341-25-5 ]
  • [ 443-75-4 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide In methanol; water at 100℃; for 2h;
  • 24
  • [ 443-75-4 ]
  • 2-(6-fluoro-1-(triisopropylsilyl)-1H-indol-3-yl)-N-(phenylsulfonyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation 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
  • 25
  • [ 443-75-4 ]
  • (3aR,8aS)-3a,6-difluoro-1-(phenylsulfonyl)-8-(triisopropylsilyl)-3,3a,8,8a-tetrahydropyrrolo[2,3-b]indol-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation 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
  • 26
  • [ 443-75-4 ]
  • [ 348133-46-0 ]
  • C17H13F2N3 [ No CAS ]
YieldReaction ConditionsOperation 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;
  • 27
  • [ 443-75-4 ]
  • [ 71-44-3 ]
  • N,N'-((butane-1,4-diylbis(azanediyl))bis(propane-3,1-diyl))bis(2-(6-fluoro-1H-indol-3-yl)acetamide) [ No CAS ]
YieldReaction ConditionsOperation 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;
  • 28
  • [ 931-23-7 ]
  • [ 443-75-4 ]
  • C15H12FNO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; triethylamine In N,N-dimethyl-formamide Reflux;
  • 29
  • [ 443-75-4 ]
  • methyl 2-(6-fluoro-1-methyl-1H-indol-3-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation 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
  • 30
  • [ 443-75-4 ]
  • 2-(6-fluoro-1-methyl-1H-indol-3-yl)malonic acid [ No CAS ]
YieldReaction ConditionsOperation 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
  • 31
  • [ 443-75-4 ]
  • C12H8Cl2FNO2 [ No CAS ]
YieldReaction ConditionsOperation 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
  • 32
  • [ 443-75-4 ]
  • C14H14FNO4 [ No CAS ]
YieldReaction ConditionsOperation 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
  • 33
  • [ 443-75-4 ]
  • 1-((6-chloropyridin-3-yl)methyl)-3-(6-fluoro-1-methyl-1H-indol-3-yl)-4-oxo-4H-pyrido[1,2-a]pyrimidinium-2-olate [ No CAS ]
YieldReaction ConditionsOperation 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
  • 34
  • [ 443-75-4 ]
  • 1-((2-chlorothiazol-5-yl)methyl)-3-(6-fluoro-1-methyl-1H-indol-3-yl)-4-oxo-4H-pyrido[1,2-a]pyrimidinium-2-olate [ No CAS ]
YieldReaction ConditionsOperation 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
  • 35
  • [ 443-75-4 ]
  • 1-((2-chlorothiazol-5-yl)methyl)-3-(6-fluoro-1-methyl-1H-indol-3-yl)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidinium-2-olate [ No CAS ]
YieldReaction ConditionsOperation 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
  • 36
  • [ 443-75-4 ]
  • 1-(2-cyanoethyl)-3-(6-fluoro-1-methyl-1H-indol-3-yl)-4-oxo-4H-pyrido[1,2-a]pyrimidinium-2-olate [ No CAS ]
YieldReaction ConditionsOperation 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
  • 37
  • [ 443-75-4 ]
  • 3-(6-fluoro-1-methyl-1H-indol-3-yl)-4-oxo-1-(pyrimidin-5-ylmethyl)-4H-pyrido[1,2-a]pyrimidinium-2-olate [ No CAS ]
YieldReaction ConditionsOperation 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
  • 38
  • [ 443-75-4 ]
  • 1-((6-chloropyridin-3-yl)methyl)-3-(1,2-dimethyl-1H-indol-3-yl)-4-oxo-4H-pyrido[1,2-a]pyrimidinium-2-olate [ No CAS ]
YieldReaction ConditionsOperation 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
  • 39
  • [ 67-56-1 ]
  • [ 443-75-4 ]
  • [ 5159-07-9 ]
YieldReaction ConditionsOperation 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%.
  • 40
  • [ 443-75-4 ]
  • 3-((5-benzyl-4-(3-(1-trityl-1H-imidazol-4-yl)propyl)-4H-1,2,4-triazol-3-yl)methyl)-6-fluoro-1H-indole [ No CAS ]
YieldReaction ConditionsOperation 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
  • 41
  • [ 443-75-4 ]
  • 6-fluoro-3-((5-(4-fluorobenzyl)-4-(3-(1-trityl-1H-imidazol-4-yl)propyl)-4H-1,2,4-triazol-3-yl)methyl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation 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
  • 42
  • [ 443-75-4 ]
  • 3-((5-(3-chlorobenzyl)-4-(3-(1-trityl-1H-imidazol-4-yl)propyl)-4H-1,2,4-triazol-3-yl)methyl)-6-fluoro-1H-indole [ No CAS ]
YieldReaction ConditionsOperation 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
  • 43
  • [ 443-75-4 ]
  • 3-((5-(3,4-dichlorobenzyl)-4-(3-(1-trityl-1H-imidazol-4-yl)propyl)-4H-1,2,4-triazol-3-yl)methyl)-6-fluoro-1H-indole [ No CAS ]
YieldReaction ConditionsOperation 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
  • 44
  • [ 443-75-4 ]
  • 3-((5-(3,5-dichlorobenzyl)-4-(3-(1-trityl-1H-imidazol-4-yl)propyl)-4H-1,2,4-triazol-3-yl)methyl)-6-fluoro-1H-indole [ No CAS ]
YieldReaction ConditionsOperation 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
  • 45
  • [ 443-75-4 ]
  • 3-((5-(3-bromobenzyl)-4-(3-(1-trityl-1H-imidazol-4-yl)propyl)-4H-1,2,4-triazol-3-yl)methyl)-6-fluoro-1H-indole [ No CAS ]
YieldReaction ConditionsOperation 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
  • 46
  • [ 443-75-4 ]
  • 6-fluoro-3-((5-(3-(trifluoromethyl)benzyl)-4-(3-(1-trityl-1H-imidazol-4-yl)propyl)-4H-1,2,4-triazol-3-yl)methyl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation 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
  • 47
  • [ 443-75-4 ]
  • 6-fluoro-3-((5-(2-methoxybenzyl)-4-(3-(1-trityl-1H-imidazol-4-yl)propyl)-4H-1,2,4-triazol-3-yl)methyl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation 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
  • 48
  • [ 443-75-4 ]
  • 6-fluoro-3-((5-(3-methoxybenzyl)-4-(3-(1-trityl-1H-imidazol-4-yl)propyl)-4H-1,2,4-triazol-3-yl)methyl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation 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
  • 49
  • [ 443-75-4 ]
  • 6-fluoro-3-((5-(4-methoxybenzyl)-4-(3-(1-trityl-1H-imidazol-4-yl)propyl)-4H-1,2,4-triazol-3-yl)methyl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation 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
  • 50
  • [ 443-75-4 ]
  • 3-((5-((6-fluoro-1H-indol-3-yl)methyl)-4-(3-(1-trityl-1H-imidazol-4-yl)propyl)-4H-1,2,4-triazol-3-yl)methyl)benzonitrile [ No CAS ]
YieldReaction ConditionsOperation 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
  • 51
  • [ 443-75-4 ]
  • 6-fluoro-3-((5-(3-(methylsulfonyl)benzyl)-4-(3-(1-trityl-1H-imidazol-4-yl)propyl)-4H-1,2,4-triazol-3-yl)methyl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation 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
  • 52
  • [ 443-75-4 ]
  • 6-fluoro-3-((5-(4-(methylsulfonyl)benzyl)-4-(3-(1-trityl-1H-imidazol-4-yl)propyl)-4H-1,2,4-triazol-3-yl)methyl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation 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
  • 53
  • [ 443-75-4 ]
  • 6-fluoro-3-((5-neopentyl-4-(3-(1-trityl-1H-imidazol-4-yl)propyl)-4H-1,2,4-triazol-3-yl)methyl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation 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
  • 54
  • [ 443-75-4 ]
  • 3,3’-((4-(3-(1-trityl-1H-imidazol-4-yl)propyl)-4H-1,2,4-triazol-3,5-diyl)bis(methylene))bis(6-fluoro-1H-indole) [ No CAS ]
YieldReaction ConditionsOperation 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
  • 55
  • [ 443-75-4 ]
  • 5-((6-fluoro-1H-indol-3-yl)methyl)-4-(3-(1-trityl-1H-imidazol-4-yl)propyl)-4H-1,2,4-triazole-3-thiol [ No CAS ]
YieldReaction ConditionsOperation 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
  • 56
  • [ 443-75-4 ]
  • 6-fluoro-3-((4-(3-(1-trityl-1H-imidazol-4-yl)propyl)-4H-1,2,4-triazol-3-yl)methyl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation 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
  • 57
  • [ 443-75-4 ]
  • C36H33FN6OS [ No CAS ]
YieldReaction ConditionsOperation 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
  • 58
  • [ 443-75-4 ]
  • 3-((4-(3-(1H-imidazol-4-yl)propyl)-5-benzyl-4H-1,2,4-triazol-3-yl)methyl)-6-fluoro-1H-indole [ No CAS ]
YieldReaction ConditionsOperation 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
  • 59
  • [ 443-75-4 ]
  • 3-((4-(3-(1H-imidazol-4-yl)propyl)-5-(4-fluorobenzyl)-4H-1,2,4-triazol-3-yl)methyl)-6-fluoro-1H-indole [ No CAS ]
YieldReaction ConditionsOperation 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
  • 60
  • [ 443-75-4 ]
  • 3-((4-(3-(1H-imidazol-4-yl)propyl)-5-(3-chlorobenzyl)-4H-1,2,4-triazol-3-yl)methyl)-6-fluoro-1H-indole [ No CAS ]
YieldReaction ConditionsOperation 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
  • 61
  • [ 443-75-4 ]
  • 3-((4-(3-(1H-imidazol-4-yl)propyl)-5-(3,4-dichlorobenzyl)-4H-1,2,4-triazol-3-yl)methyl)-6-fluoro-1H-indole [ No CAS ]
YieldReaction ConditionsOperation 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
  • 62
  • [ 443-75-4 ]
  • 3-((4-(3-(1H-imidazol-4-yl)propyl)-5-(3,5-dichlorobenzyl)-4H-1,2,4-triazol-3-yl)methyl)-6-fluoro-1H-indole [ No CAS ]
YieldReaction ConditionsOperation 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
  • 63
  • [ 443-75-4 ]
  • 3-((4-(3-(1H-imidazol-4-yl)propyl)-5-(3-bromobenzyl)-4H-1,2,4-triazol-3-yl)methyl)-6-fluoro-1H-indole [ No CAS ]
YieldReaction ConditionsOperation 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
  • 64
  • [ 443-75-4 ]
  • 3-((4-(3-(1H-imidazol-4-yl)propyl)-5-(3-(trifluoromethyl)benzyl)-4H-1,2,4-triazol-3-yl)methyl)-6-fluoro-1H-indole [ No CAS ]
YieldReaction ConditionsOperation 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
  • 65
  • [ 443-75-4 ]
  • 3-((4-(3-(1H-imidazol-4-yl)propyl)-5-(2-methoxybenzyl)-4H-1,2,4-triazol-3-yl)methyl)-6-fluoro-1H-indole [ No CAS ]
YieldReaction ConditionsOperation 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
  • 66
  • [ 443-75-4 ]
  • 3-((4-(3-(1H-imidazol-4-yl)propyl)-5-(3-methoxybenzyl)-4H-1,2,4-triazol-3-yl)methyl)-6-fluoro-1H-indole [ No CAS ]
YieldReaction ConditionsOperation 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
  • 67
  • [ 443-75-4 ]
  • 3-((4-(3-(1H-imidazol-4-yl)propyl)-5-(4-methoxybenzyl)-4H-1,2,4-triazol-3-yl)methyl)-6-fluoro-1H-indole [ No CAS ]
YieldReaction ConditionsOperation 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
  • 68
  • [ 443-75-4 ]
  • 3-((4-(3-(1H-imidazol-4-yl)propyl)-5-((6-fluoro-1H-indol-3-yl)methyl)-4H-1,2,4-triazol-3-yl)methyl)benzonitrile [ No CAS ]
YieldReaction ConditionsOperation 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
  • 69
  • [ 443-75-4 ]
  • 3-((4-(3-(1H-imidazol-4-yl)propyl)-5-(3-(methylsulfonyl)benzyl)-4H-1,2,4-triazol-3-yl)methyl)-6-fluoro-1H-indole [ No CAS ]
YieldReaction ConditionsOperation 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
  • 70
  • [ 443-75-4 ]
  • 3-((4-(3-(1H-imidazol-4-yl)propyl)-5-(4-(methylsulfonyl)benzyl)-4H-1,2,4-triazol-3-yl)methyl)-6-fluoro-1H-indole [ No CAS ]
YieldReaction ConditionsOperation 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
  • 71
  • [ 443-75-4 ]
  • 3-((4-(3-(1H-imidazol-4-yl)propyl)-5-neopentyl-4H-1,2,4-triazol-3-yl)methyl)-6-fluoro-1H-indole [ No CAS ]
YieldReaction ConditionsOperation 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
  • 72
  • [ 443-75-4 ]
  • 3,3’-((4-(3-(1H-imidazol-4-yl)propyl)-4H-1,2,4-triazol-3,5-diyl)bis(methylene))bis(6-fluoro-1H-indole) [ No CAS ]
YieldReaction ConditionsOperation 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
  • 73
  • [ 443-75-4 ]
  • 3-((4-(3-(1H-imidazol-4-yl)propyl)-4H-1,2,4-triazol-3-yl)methyl)-6-fluoro-1H-indole [ No CAS ]
YieldReaction ConditionsOperation 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
  • 74
  • [ 443-75-4 ]
  • 2-(6-fluoro-1H-indol-3-yl)-N-(3-(1-trityl-1H-imidazol-4-yl)propyl)ethanethioamide [ No CAS ]
YieldReaction ConditionsOperation 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
  • 75
  • [ 443-75-4 ]
  • 2-(6-fluoro-1H-indol-3-yl)acetic hydrazide hydrochloride [ No CAS ]
YieldReaction ConditionsOperation 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
  • 76
  • [ 443-75-4 ]
  • [ 870-46-2 ]
  • tert-butyl 2-(2-(6-fluoro-1H-indol-3-yl)acetyl)hydrazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation 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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2-(5,6-Difluoro-1H-indol-3-yl)acetic acid

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Chemical Structure| 89434-03-7

[ 89434-03-7 ]

2-(4-Fluoro-1H-indol-3-yl)acetic acid

Similarity: 0.96

Chemical Structure| 1227572-83-9

[ 1227572-83-9 ]

2-(4,6-Difluoro-1H-indol-3-yl)acetic acid

Similarity: 0.95

Chemical Structure| 126030-75-9

[ 126030-75-9 ]

2-(4,5-Difluoro-1H-indol-3-yl)acetic acid

Similarity: 0.93

Carboxylic Acids

Chemical Structure| 443-73-2

[ 443-73-2 ]

5-Fluoroindole-3-acetic acid

Similarity: 0.98

Chemical Structure| 126030-73-7

[ 126030-73-7 ]

2-(5,6-Difluoro-1H-indol-3-yl)acetic acid

Similarity: 0.96

Chemical Structure| 89434-03-7

[ 89434-03-7 ]

2-(4-Fluoro-1H-indol-3-yl)acetic acid

Similarity: 0.96

Chemical Structure| 1227572-83-9

[ 1227572-83-9 ]

2-(4,6-Difluoro-1H-indol-3-yl)acetic acid

Similarity: 0.95

Chemical Structure| 126030-75-9

[ 126030-75-9 ]

2-(4,5-Difluoro-1H-indol-3-yl)acetic acid

Similarity: 0.93

Related Parent Nucleus of
[ 443-75-4 ]

Indoles

Chemical Structure| 443-73-2

[ 443-73-2 ]

5-Fluoroindole-3-acetic acid

Similarity: 0.98

Chemical Structure| 126030-73-7

[ 126030-73-7 ]

2-(5,6-Difluoro-1H-indol-3-yl)acetic acid

Similarity: 0.96

Chemical Structure| 89434-03-7

[ 89434-03-7 ]

2-(4-Fluoro-1H-indol-3-yl)acetic acid

Similarity: 0.96

Chemical Structure| 1227572-83-9

[ 1227572-83-9 ]

2-(4,6-Difluoro-1H-indol-3-yl)acetic acid

Similarity: 0.95

Chemical Structure| 126030-75-9

[ 126030-75-9 ]

2-(4,5-Difluoro-1H-indol-3-yl)acetic acid

Similarity: 0.93