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CAS No. : | 98081-84-6 | MDL No. : | MFCD04966992 |
Formula : | C10H8ClNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HHDCCGVOJXWGEU-UHFFFAOYSA-N |
M.W : | 209.63 | Pubchem ID : | 4715032 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.1 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 54.59 |
TPSA : | 42.09 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.55 cm/s |
Log Po/w (iLOGP) : | 2.23 |
Log Po/w (XLOGP3) : | 2.86 |
Log Po/w (WLOGP) : | 2.61 |
Log Po/w (MLOGP) : | 1.94 |
Log Po/w (SILICOS-IT) : | 2.99 |
Consensus Log Po/w : | 2.53 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.29 |
Solubility : | 0.109 mg/ml ; 0.000519 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.4 |
Solubility : | 0.0829 mg/ml ; 0.000395 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.98 |
Solubility : | 0.0218 mg/ml ; 0.000104 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.62 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280 | UN#: | N/A |
Hazard Statements: | H302-H317 | 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 |
---|---|---|
50% | With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 5 h; Cooling with ice | General procedure: A solution of indole-2-carboxylate 11 (1 mmol) in THF (10 mL)was added dropwise to a suspension of LiAlH4 (0.8 mmol) in THF(20 mL) under cooling with ice-water. After stirring at rt for 5 h, thereaction mixture was quenched with water, and then was filtratedthrough a Celite pad. The filtrate was extracted with EtOAc. Theorganic layer was washed with brine, dried over Na2SO4, andevaporated in vacuo. The residue was purified by column chromatography using EtOAc-hexane as an eluent to give thealcohol 12. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With hydrazine hydrate In ethanol for 5h; Reflux; | |
With hydrazine hydrate In isopropyl alcohol at 60℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | In xylene for 0.333333h; Heating; | |
96% | With Rh4(3,3'-[1,3-phenylenebis(ethyne-2,1-diyl)]dibenzoicacid(-H))4(H2O)2(dimethylacetamide)2 In toluene at 85℃; for 5h; | |
88.6% | In 5,5-dimethyl-1,3-cyclohexadiene Inert atmosphere; Reflux; |
85% | In toluene at 60℃; for 16h; | |
56% | With iron(II) triflate In tetrahydrofuran at 80℃; for 24h; Sealed tube; Inert atmosphere; | |
50% | With tetrabutylammonium tricarbonylnitrosylferrate In chloroform at 80℃; for 1h; Inert atmosphere; Microwave irradiation; | |
In hexane at 200℃; for 0.166667h; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride at 20℃; | ||
With sulfuric acid at 20 - 80℃; for 4h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 6-chloro-2-methoxycarbonylindole With sodium hydride In N,N-dimethyl-formamide at 20℃; Stage #2: 3-(bromomethyl)-5-(5-chlorothiophen-2-yl)isoxazole In N,N-dimethyl-formamide at 80℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; hexane; toluene at 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38 mg | With potassium cyanide; hydroxylamine In tetrahydrofuran; methanol at 20℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 63 percent / sodium methoxide / methanol / 4 h / -10 °C 2: 85 percent / Rh2(pbf)4 / toluene / 16 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 76 percent / 5 h / 90 °C 2: 72 percent / AlCl3 / CH2Cl2 / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: K2CO3 / acetone / 12 h / 60 °C 2: 76 percent / 5 h / 90 °C 3: 72 percent / AlCl3 / CH2Cl2 / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: NaH / dimethylformamide / 20 °C 1.2: dimethylformamide / 80 °C 2.1: lithium hydroxide monohydrate / tetrahydrofuran / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: NaH / dimethylformamide / 20 °C 1.2: dimethylformamide / 80 °C 2.1: lithium hydroxide monohydrate / tetrahydrofuran / 60 °C 3.1: NEt3; bis(oxo-3-oxazolidinyl)phosphoryl chloride / CH2Cl2 / 20 °C 3.2: CH2Cl2 / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 85percent aq. hydrazine / propan-2-ol / 1 h / 60 °C 2: CH2Cl2 / 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 74 percent / Na, CH3OH / 3 h / Ambient temperature 2: 97 percent / xylene / 0.33 h / Heating | ||
Multi-step reaction with 2 steps 1: sodium methylate / methanol / -20 - -10 °C / Inert atmosphere 2: iron(II) triflate / tetrahydrofuran / 24 h / 80 °C / Sealed tube; Inert atmosphere | ||
Multi-step reaction with 2 steps 1: sodium; methanol / -10 °C 2: tetrakis(trifluoroacetato)rhodium(II) / toluene / 0.33 h / 95 °C / Microwave irradiation |
Multi-step reaction with 2 steps 1: sodium methylate / methanol / 3 h / -10 °C 2: 5,5-dimethyl-1,3-cyclohexadiene / 1 h / Reflux; Inert atmosphere | ||
Multi-step reaction with 2 steps 1: sodium methylate / methanol / -20 - 0 °C 2: 5,5-dimethyl-1,3-cyclohexadiene / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In N,N-dimethyl-formamide | 1 Methyl 6-chloro-1-(cyanomethyl)-indole-2-carboxylate Methyl 6-chloro-1-(cyanomethyl)-indole-2-carboxylate To a stirred solution of methyl 6-chloroindole-2-carboxylate (9.8 g, 46.7 mmol) (D. Knittel, Synthesis, 1985, 2, 186-188) in DMF (80 mL) under Ar at ambient temperature was added sodium hydride (60%; 2.80 g, 70 mmol) portionwise over 10 min. After 30 min, chloroacetonitrile (5.9 mL, 93.2 mmol) was added dropwise and the resultant mixture was heated at 75 °C (bath temp.) for 45 min, then allowed to cool. The reaction mixture was poured onto ice (500 mL) and the solid product was filtered, washed with ice-cold water (100 mL), and triturated with refluxing ethanol (150 mL). After allowing to cool to ambient temperature, then cooling in ice, the solid product was filtered-off and washed with ice-cold ethanol (50 mL) to afford the title compound (9.49 g, 82%) as a light grey solid: mp 177-8 °C; IR νmax (Nujol)/cm-1; 3094, 2955, 2925, 2854, 1713, 1613, 1568, 1527, 1519, 1448, 1421, 1398, 1378, 1336, 1306, 1260, 1150, 1108, 1060, 943, 908, 834, 802, 761, 737, 682, 618, 597, 518 and 478; NMR δH (400 MHz, DMSO-d6) 3.95 (3H, s), 5.56 (2H, s), 7.22 (1H, dd, J 8.5, 2 Hz), 7.34 (1H, d, J 1 Hz), 7.43 (1H, br s) and 7.62 (1H, d, J 8.5 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With tetrakis(trifluoroacetato)rhodium(II) In toluene at 95℃; for 0.333333h; Microwave irradiation; | |
89% | With 5,10,15,20-tetrakis(pentafluorophenyl)-21H,23H-porphyrin iron(III) chloride In 1,2-dichloro-ethane for 24h; Molecular sieve; Reflux; Inert atmosphere; | |
85% | With dirhodium(II) tetrakis(perfluorobutyrate) In toluene at 40℃; Inert atmosphere; |
In 5,5-dimethyl-1,3-cyclohexadiene for 1h; Reflux; Inert atmosphere; | General procedure for the synthesis of 4-methoxy-1H-indole-2-carboxylic acid methyl ester (7).2 General procedure: Azido ether (6) (3.7g, 15.86 mmol, 1 equiv) dissolved in xylene (100 mL) was added dropwise to refluxing xylene (150 mL) under argon. The solution was reflux for 1h, after which it was evaporated under reduced pressure. The resulting solid was flash chromatographed on silica gel using hexane/EtOAc (4:1) to give a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 6-chloro-2-methoxycarbonylindole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.333333h; Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1h; | General procedure for the synthesis of methyl 1-benzyl-4-methoxy-1H-indole-2-carboxylate (8).2 General procedure: 4-methoxy-1H-indole-2-carboxylic acid methyl ester (7) (3g, 10 mmol, 1 equiv) was dissolved in DMF (4 mL) and the resulting solution was added dropwise to a suspension of NaH (60% in mineral oil) (0.6g, 15 mmol, 1.5 equiv) in DMF (10 mL) at 0 °C. The mixture was stirred for 20 min at 0 °C and benzyl bromide (2 mL, 17 mmol, 1.7 equiv) was added dropwise. The mixture was allowed to warm to room temperature and stirred for 1h, before quenching the reaction by pouring it onto ice. The organic layer was diluted with EtOAc (20 mL) and separated from the aqueous one. The latter was extracted with EtOAc (3×20 mL). The combined organic layers were wash with water (20 mL) and brine (20 mL), were dried over MgSO4, filtered and concentrated in vacue to afford as yellow solid, which did not require further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 0 °C 1.2: 1 h / 0 - 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran; toluene / 0.5 h / 0 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 0 °C 1.2: 1 h / 0 - 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran; toluene / 0.5 h / 0 °C / Inert atmosphere 3.1: manganese(IV) oxide / tetrahydrofuran / 4 h / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 0 °C 1.2: 1 h / 0 - 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran; toluene / 0.5 h / 0 °C / Inert atmosphere 3.1: manganese(IV) oxide / tetrahydrofuran / 4 h / Inert atmosphere 4.1: titanium(IV) tetraethanolate / toluene / 4 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 0 °C 1.2: 1 h / 0 - 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran; toluene / 0.5 h / 0 °C / Inert atmosphere 3.1: manganese(IV) oxide / tetrahydrofuran / 4 h / Inert atmosphere 4.1: titanium(IV) tetraethanolate / toluene / 4 h / Reflux 5.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 4 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 0 °C 1.2: 1 h / 0 - 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran; toluene / 0.5 h / 0 °C / Inert atmosphere 3.1: manganese(IV) oxide / tetrahydrofuran / 4 h / Inert atmosphere 4.1: titanium(IV) tetraethanolate / toluene / 4 h / Reflux 5.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 4 h / 0 - 20 °C 6.1: triphenylphosphine; diethylazodicarboxylate / toluene / Inert atmosphere 7.1: triphenylphosphine gold(I)chloride / dichloromethane / 5 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 0 °C 1.2: 1 h / 0 - 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran; toluene / 0.5 h / 0 °C / Inert atmosphere 3.1: manganese(IV) oxide / tetrahydrofuran / 4 h / Inert atmosphere 4.1: titanium(IV) tetraethanolate / toluene / 4 h / Reflux 5.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 4 h / 0 - 20 °C 6.1: triphenylphosphine; diethylazodicarboxylate / toluene / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With 1,4-diaza-bicyclo[2.2.2]octane; copper(l) iodide; potassium carbonate In 1,4-dioxane for 3h; Schlenk technique; Inert atmosphere; Reflux; | General Procedure forthe CuI Catalyzed Intramolecule Coupling Reaction Using 3-(2-Aminophenyl)-2-Bromo-acrylates (2a-2t): General procedure: A dried 50 mL Schlenk tubeequipped with a rubber septum and magnetic stir bar was charged with3-(2-aminophenyl)-2-bromoacrylate (128 mg, 0.5 mmol), K2CO3(345 mg, 2.5 mmol), CuI (9.5 mg, 0.05 mmol), DABCO (0.1 mmol) and dioxane (4mL). The mixture was degassed 3 times under N2 atmosphere thenheated at reflux until the starting material was consumed as indicated by TLC.The cooled mixture was partitioned between 20 mL of water and 20 mL of ethylacetate. The organic layer was separated, and the aqueous layer was extractedwith ethyl acetate (10 mL x 2). The combined organic layers were dried (Na2SO4)and concentrated. The residue was purified by flash chromatography on silicagel eluted with petroleum/ethylacetate to provide corresponding 2-carboxyindole. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetic acid; iron / ethanol / 0.08 h / 20 °C / Reflux 2: potassium carbonate; 1,4-diaza-bicyclo[2.2.2]octane; copper(l) iodide / 1,4-dioxane / 3 h / Schlenk technique; Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: dimethylbromosulphonium bromide / dichloromethane / 1 h / 20 °C / Inert atmosphere 1.2: -78 - 20 °C / Inert atmosphere 2.1: acetic acid; iron / ethanol / 0.08 h / 20 °C / Reflux 3.1: potassium carbonate; 1,4-diaza-bicyclo[2.2.2]octane; copper(l) iodide / 1,4-dioxane / 3 h / Schlenk technique; Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: aluminum (III) chloride / 1,2-dichloro-ethane / Inert atmosphere; Reflux 2: triethylsilane; trifluoroacetic acid / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: aluminum (III) chloride / 1,2-dichloro-ethane / Inert atmosphere; Reflux 2.1: triethylsilane; trifluoroacetic acid / 0 - 20 °C 3.1: sodium hydroxide / ethanol; water / 2 h / Reflux 3.2: 20 °C / pH 2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: aluminum (III) chloride / 1,2-dichloro-ethane / Inert atmosphere; Reflux 2.1: triethylsilane; trifluoroacetic acid / 0 - 20 °C 3.1: sodium hydroxide / ethanol; water / 2 h / Reflux 3.2: 20 °C / pH 2 4.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58.8% | With aluminum (III) chloride In 1,2-dichloro-ethane Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: hydrazine hydrate / ethanol / 5 h / Reflux 2: acetic acid; sodium nitrite / water; 1,4-dioxane / 0 °C 3: Reflux 4: 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: hydrazine hydrate / ethanol / 5 h / Reflux 2: acetic acid; sodium nitrite / water; 1,4-dioxane / 0 °C 3: Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: hydrazine hydrate / ethanol / 5 h / Reflux 2: acetic acid; sodium nitrite / water; 1,4-dioxane / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: hydrazine hydrate / ethanol / 5 h / Reflux 2: acetic acid; sodium nitrite / water; 1,4-dioxane / 0 °C 3: Reflux 4: 0 °C 5: tetrahydrofuran / 0 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: hydrazine hydrate / ethanol / 5 h / Reflux 2: acetic acid; sodium nitrite / water; 1,4-dioxane / 0 °C 3: Reflux 4: 0 °C 5: tetrahydrofuran / 0 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In methanol; water for 2.5h; Reflux; Inert atmosphere; Acidic conditions; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 5 h / 20 °C / Cooling with ice 2: manganese(IV) oxide / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 5 h / 20 °C / Cooling with ice 2.1: manganese(IV) oxide / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere 3.1: potassium hydroxide / N,N-dimethyl-formamide / 0.5 h / Cooling with ice 3.2: 4 h / 20 °C / Cooling with ice |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 5 h / 20 °C / Cooling with ice 2.1: manganese(IV) oxide / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere 3.1: potassium hydroxide / N,N-dimethyl-formamide / 0.5 h / Cooling with ice 3.2: 4 h / 20 °C / Cooling with ice 4.1: 2,6-di-tert-butyl-4-methyl-phenol; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 7 h / 70 °C / 760.05 Torr / Inert atmosphere 4.2: 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 5 h / 20 °C / Cooling with ice 2.1: manganese(IV) oxide / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere 3.1: potassium hydroxide / N,N-dimethyl-formamide / 0.5 h / Cooling with ice 3.2: 4 h / 20 °C / Cooling with ice 4.1: 2,6-di-tert-butyl-4-methyl-phenol; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 7 h / 70 °C / 760.05 Torr / Inert atmosphere 4.2: 1 h / 20 °C 5.1: tetrahydrofuran / 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 5 h / 20 °C / Cooling with ice 2.1: manganese(IV) oxide / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere 3.1: potassium hydroxide / N,N-dimethyl-formamide / 0.5 h / Cooling with ice 3.2: 4 h / 20 °C / Cooling with ice 4.1: 2,6-di-tert-butyl-4-methyl-phenol; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 7 h / 70 °C / 760.05 Torr / Inert atmosphere 4.2: 1 h / 20 °C 5.1: tetrahydrofuran / 1 h 6.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; oxygen / toluene / 0.5 h / 70 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With lithium aluminium tetrahydride; In tetrahydrofuran; at 20℃; for 5.0h;Cooling with ice; | General procedure: A solution of indole-2-carboxylate 11 (1 mmol) in THF (10 mL)was added dropwise to a suspension of LiAlH4 (0.8 mmol) in THF(20 mL) under cooling with ice-water. After stirring at rt for 5 h, thereaction mixture was quenched with water, and then was filtratedthrough a Celite pad. The filtrate was extracted with EtOAc. Theorganic layer was washed with brine, dried over Na2SO4, andevaporated in vacuo. The residue was purified by column chromatography using EtOAc-hexane as an eluent to give thealcohol 12. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine; dmap / dichloromethane / 3 h / 0 - 25 °C 2: diisobutylaluminium hydride / dichloromethane; toluene / 4 h / -70 - -40 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: triethylamine; dmap / dichloromethane / 3 h / 0 - 25 °C 2: diisobutylaluminium hydride / dichloromethane; toluene / 4 h / -70 - -40 °C 3: thionyl chloride / dichloromethane / 2 h / 0 - 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; triethylamine In dichloromethane at 0 - 25℃; for 3h; | 1-tert-butyl 2-methyl 6-chloro-1H-indole-1,2-dicarboxylate To a solution of methyl 6-chloro-1H-indole-2-carboxylate (4.6 g, 21.9 mmol), Et3N (6.65 g, 65.7 mmol) and DMAP (268 mg, 2.19 mmol) in DCM (70 mL) was added dropwise Boc2O (5.74 g, 26.3 mmol) at 0 °C. The mixture was warmed to 25 °C and stirred for 3 h. The reaction mixture was diluted in DCM (60 mL) and washed with water (1 * 80 mL) and brine (1 * 80 mL), dried over Na2SO4, concentrated and purified by flash chromatography (O1O% EAPE) to give the product. ESI 254.1 (M-56+H)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: aluminum (III) chloride / 1,2-dichloro-ethane / 0 - 20 °C / Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 80 °C / Inert atmosphere 3: manganese(IV) oxide / ethyl acetate / 20 - 100 °C / Inert atmosphere 4: piperidine; acetic acid / toluene / 140 °C / Inert atmosphere; Dean-Stark 5: hydrogen; palladium 10% on activated carbon / methanol / 50 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With aluminum (III) chloride In 1,2-dichloro-ethane at 0 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | Stage #1: methanol; 4-(2,4-dichloro-benzylidene)-2-phenyl-4<i>H</i>-oxazol-5-one In N,N-dimethyl-formamide at 70℃; for 1h; Stage #2: With copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide at 110℃; for 4h; | The synthesis of compounds 2 and 6 General procedure: A 25 ml round bottom flask was charged with 3 (1mmol), R1OH (5equiv.) or R2NHR3 (5 equiv.), DMF (5 ml). The reaction was allowed to stir ar 70°C for 1h. Then, CuI (10 mol%), and K2CO3 (1 equiv.) were added and stirred at 110°C. After the completion of the reaction (as indicated by TLC), the reaction mixture was added EtOAc (10 ml) and washed with a solution of NaCl (3*10 ml). The organic layers were dried with anhydrous Na2SO4 and concentrated in vacuo. The residue was then purified by column chromatography on silica gel (n-hexanes/EtOAc = 20:1) to indole-2-carboxylic ester 2 or indole-2-carboxylic amide 6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In tetrahydrofuran for 15h; Reflux; | 1 Preparation of Intermediate III from Compound I: General procedure: Add 1.0 millimoles of compound I and 5 milliliters of tetrahydrofuran into a single-neck flask, add 1.0 millimoles of 1,5,7-triazabicyclodec-5-ene and 5.0 millimoles of compound II under stirring, and react under reflux for 15 hours After the reaction is over, the solvent is removed under reduced pressure, and the residue is separated and purified by 300-400 mesh silica gel column chromatography (the eluent is a mixed solution of ethyl acetate-petroleum ether, Vpetroleum ether: Vethyl acetateis 3: 1) Intermediate III can be obtained with a yield of 53-83%.Use the above method to prepare the following intermediate III: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 4h; Inert atmosphere; |
Tags: 98081-84-6 synthesis path| 98081-84-6 SDS| 98081-84-6 COA| 98081-84-6 purity| 98081-84-6 application| 98081-84-6 NMR| 98081-84-6 COA| 98081-84-6 structure
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P265 | Wash skin thouroughly after handling. |
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P272 | Contaminated work clothing should not be allowed out of the workplace. |
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H242 | Heating may cause a fire |
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H260 | In contact with water releases flammable gases which may ignite spontaneously |
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Health hazards | |
Code | Phrase |
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H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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