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CAS No. : | 10601-19-1 | MDL No. : | MFCD00005623 |
Formula : | C10H9NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | TUWARWGEOHQXCO-UHFFFAOYSA-N |
M.W : | 175.18 | Pubchem ID : | 82758 |
Synonyms : |
|
Num. heavy atoms : | 13 |
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 : | 50.18 |
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) : | -6.32 cm/s |
Log Po/w (iLOGP) : | 1.48 |
Log Po/w (XLOGP3) : | 1.48 |
Log Po/w (WLOGP) : | 1.99 |
Log Po/w (MLOGP) : | 0.57 |
Log Po/w (SILICOS-IT) : | 2.65 |
Consensus Log Po/w : | 1.63 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.24 |
Solubility : | 1.01 mg/ml ; 0.00577 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.97 |
Solubility : | 1.87 mg/ml ; 0.0107 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.36 |
Solubility : | 0.0772 mg/ml ; 0.000441 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.28 |
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 |
---|---|---|
94% | Stage #1: at 0℃; for 1 h; Stage #2: at 20℃; for 5 h; Stage #3: With sodium hydroxide In N,N-dimethyl-formamide at 100℃; for 0.166667 h; |
General procedure: Oxalyl chloride (0.3 mL) was added in a drop-wise manner to cooled (ice-bath) DMF (3 mL) under stirring. The mixture was then stirred at 0 °C for 1 h. A solution of the substituted indole (4 mmol) in DMF (1.5 mL) was then added to the reaction mixture in a dropwise manner. The resulting mixture was stirred at room temperature for 5 h. A 2 N solution of sodium hydroxide (2 mL) was then added, and the mixture was heated at 100 °C for 10 min. The mixture was then cooled and extracted with ethyl acetate (3 X 50 mL). The organic layers were combined and washed with sequentially water and brine. The organics were dried (Na2SO4) and distilled to dryness to give the crude residue, which was purified by flash column chromatography using ethyl acetate/petroleum ether (3:1, v/v) as the eluent to give pure indole-3-carbaldehyde (4a-k). |
92% | at 0 - 55℃; for 2 h; | General procedure: To a solution of compounds 17a, 17b (10 mmol) in 20 mL of DMF, phosphorus oxychloride (1.4 mL, 15 mmol) was added dropwise at 0°C. In 2 h of the reaction at 55°C, the mixture was poured into 150 mL of ice water. 20 percent NaOH solution was added to adjust pH at 8.0. The crude product was filtered off and recrystallized from anhydrous ethanol to give the corresponding product. |
89.4% | at 35℃; | General procedure: To a stirring solution of POCl3 (18.36 g, 0.120 mol) in DMF (25 mL), indole (11.7 g, 0.100 mol) in DMF (15 mL) was added dropwise. The mixture was stirred at 35°C for 1 h, and then be poured into ice water and neutralized with 20 percent NaOH aq. The solution was filtered and the residue was washed with water and dried under IR to give the compound 4a as yellow needle (13.86 g, 95.48 percent). Mp = 192–194°C, lit.31 Mp = 196–197°C. |
85% | Stage #1: at 0℃; Stage #2: at 0℃; for 0.5 h; Stage #3: With sodium hydroxide In waterCooling with ice; Reflux |
Synthesis of 5-methoxy-indole-3-carbaldehydes; Preparation of S-methoxy-indole-3-carbaldehyde, 5-methoxy-2-methyl-indole-3- carbaldehyde, and 3-formyl-5-methoxy-indole-2-carboxylic acid POCI3 (1.6 ml_, 17 mmol, 1.1 eq.) was added to DMF (6 mL) at 00C and the solution was stirred for 30 minutes. This mixture was added to a stirring solution of the selected 5-methoxy- indole (15.5 mmol, 1 eq.) in DMF (11.5 mL) at 00C. The resulting mixture was stirred at 00C for 30 minutes, then allowed to warm to room temperature. The reaction was poured into ice, basified to pH 10 with 5 N NaOH, warmed to room temperature, refluxed for 5 minutes and allowed to cool to rt. Finally, it was acidified to pH 4 with 2 N HCI and the resulting precipitate was filtered and washed with water until pH 7. The solid product was dried under vacuum.5-Methoxy-indole-3-carbaldehydeYield: 85percent. MS (m/z): 176.2 (MH+). |
83% | at 0 - 40℃; for 1.5 h; | General procedure: Phosphorus oxychloride (0.42 g, 2.74 mmol) was added dropwise to a solution of the indole 5b, 5e–5g (0.30 g, 2.29 mmol) in DMF (0.84 g, 11.4 mmol) at 0 °C for 30 min. The solution was then heated at 40 °C for 1 h. Ice was added to the reaction vessel, followed by a solution of sodium hydroxide (2 M). The solution was refluxed for 40 min. The mixture was cooled and extracted using ethyl acetate, and the organic phase was washed with brine. The organic extracts were combined, dried over Na2SO4, and concentrated. The crude residue was purified by chromatography on a silica gel column using hexane-ethyl acetate as an eluent to obtain the desired product [19]. |
79% | at 20℃; for 1 h; | A 5-methoxy-1H-indole (14.7 g, 0.1 mol) was dissolved in N, N -dimethylformamide (73.5 g, 1 mol) in a 500ml of reaction flask at 0 ° C with mechanical agitation, then phosphorus pentachloride / N, N -dimethylformamide mixed formylation reagent (15 g, 0.12 mol) was added in portions. The reaction mixture was stirred at room temperature for 1 hour. After completion of the reaction, 100 mL of water was added and stirred at room temperature for 1 hour. The reaction was neutralized with 2N sodium hydroxide solution and the resulting suspension was filtered. The filter cake was dissolved in methanol / tetrahydrofuran and the pH was adjusted to 1 with concentrated hydrochloric acid. The solution was stirred at room temperature for 45 minutes and neutralized with 4N sodium hydroxide solution to neutral. The solvent was partially evaporated to give the product, filtered and washed with water. Finally, 5-methoxy-1-hydrogen-indole-3- carboxaldehyde was obtained (14 g, 79percent). This product can be used in the production of Tegaserod Hydrogen Maleate. |
69% | Stage #1: at 20℃; for 0.75 h; Cooling with ice Stage #2: at 40℃; for 1.25 h; |
The Vilsmeier-Haack reagent was generated by the addition of 2 ml of POCI3 over the course of15 minutes to 8 ml of DMF cooled in an ice-salt bath. After the addition was complete, the icebath was removed and the contents of the flask allowed to warm to room temperature overapprox. 30 minutes. The substituted indole (21.9 mmol) was dissolved in 10 ml of DMF andadded over a period of 15 minutes to the formylating mixture. The stirring was continued for an10 hour during which the flask contents were heated to 40°C in a hot water bath. A total of 50 mlice cold H20 and 20 ml of 5 M NaOH were added, the mixture quickly brought to a boil and leftto cool slowly. The crystals were removed by filtration, washed with cold water and vacuumdried. The products thus obtained were in most cases sufficiently pure for the subsequentreactions, and the impure aldehydes were recrystallized from ethanol-water mixtures. Yields15 varied from 48 to 90percent.; The compound was synthesized from 5-methoxy-1H-indole (170 mmol) according to the25 general procedure 2, with the exception that it was scaled up proportionally to the 5-methoxyindole (69percent yield).LC-MS: m/z = 176.11; tR = 2.20 min. |
63% | at 20℃; for 1 h; | (a) 5-methoxyindole (200 mg, 1.36 mmol) dissolved in anhydrous DMF,Drip the newly prepared Vilsmeier reagent,Allow to react at room temperature for one hour, then pour into ice water and filter by suction.Dryed to a yellow solid 150 mg, yield 63percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With iodine; oxygen; pyrographite In N,N-dimethyl-formamide at 120℃; for 0.8 h; | General procedure: A 50 mL round bottom flask equipped with a magnetic stirring bar was charged with substituted indole 1 (1.0 mmol, 1.0 equiv), HMTA (2.0 mmol, 0.2803 g, 2.0 equiv), activated carbon (0.1 g) and DMF (2 mL). Then I2 (0.2 mmol, 0.0507g, 20 molpercent) was added and the flask was equipped with a reflux condenser. The reaction mixture was stirred at 120 oC under open air and monitored by TLC. Upon completion of the reaction, the reaction mixture was cooled to room temperature. The resultant mixture was filtered through a pad of celite and the filter cake was washed thoroughly with EtOAc (4 × 6 mL). The filtrate was washed with 0.5 M aqueous HCl (10 mL), saturated NaHCO3 solution (10 mL) and saturated NaCl solution ( 10 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluted with hexane and ethyl acetate to give the product. |
60% | With silica supported ceric ammonium nitrate In acetonitrile for 15 h; Reflux | General procedure: a mixture of indole (1 mmol), HMTA (2.5 mmol), and 10percent CAN–SiO2 was refluxed in CH3CN (5.0 mL). After the reaction was complete, the mixture was evaporated to give a crude residue of CAN–SiO2 and product. The crude residue was washed with EtOAc (10 mL 5) and dried to leave a crude product that was purified by short flash column chromatography (EtOAc/hexane = 1:3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With water; iodine; oxygen; sodium carbonate In 1,4-dioxane at 100℃; for 36 h; Schlenk technique; Sealed tube | General procedure: Under air, a 20 mL of Schlenk tube equipped with a stir bar was charged with indole 1 (0.2 mmol, 1 equiv),TMEDA (75 µL, 0.5 mmol, 2.5 equiv), Na2CO3 (42.4 mg, 0.4mmol, 2.0 equiv), 1,4-dioxane (0.5 mL) and H2O (100 µL). Then I2 (101.5 mg, 0.4 mmol, 2.0 equiv) was added and the tube was sealed with a rubber plug and charged with O2. The reaction mixture was stirred at 100 °C for 36 h in oil bath. After cooling to room temperature, the resultant mixture was evaporated with EtOAc (20 mL) under reduced pressure and the residue was purified by flash column chromatography on a silica gel to give the products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With iron(III) chloride; ammonia In water; N,N-dimethyl-formamide at 130℃; for 1 h; | General procedure: A 50 mL round-bottomed flask equipped with a magnetic stirringbar was charged with the appropriate indole 1 (0.5 mmol,1.0 equiv), 37percent aq HCHO (0.5 mmol, 0.0406 g, 1.0 equiv), 25percent aqNH3 (1.0 mmol, 0.0681 g, 2.0 equiv), FeCl3 (0.01 mmol, 0.0016 g,2 molpercent), and DMF (2 mL). The flask was fitted with a reflux condenser,and the mixture was stirred at 130 °C under open air.When the reaction was complete (TLC), the mixture was cooledto r.t., diluted with sat. aq NaCl (10 mL) and 0.5 M aq HCl (2 mL),and extracted with EtOAc (3 x 7 mL). The organic layers werecombined, washed with sat. aq NaHCO3 (10 mL) and sat. aq NaCl(10 mL), dried (Na2SO4), and concentrated under reduced pressure.The residue was purified by flash column chromatography(silica gel, hexane–EtOAc). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With pyridinium chlorochromate In N,N-dimethyl-formamide at 100℃; for 0.5 h; | General procedure: PCC (1.1 mmol) was added to a stirred solution of 4 (1mmol) in DMF (5 mL) at 100 °C (pre-heated oil bath) and the mixture was stirred at 100 °C for 0.5 h.After cooling, the resulting mixture was added to 10percent aqueous HCl solution, extracted with AcOEt (100mL), washed with brine, and dried over MgSO4. The solvent was removed, and the residue was purifiedby silica gel column chromatography with CH2Cl2 to give 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With sodium hydrogencarbonate In N,N-dimethyl-formamide; mineral oil | a. 5-Methoxy-1-methylindole-3-carboxaldehyde (43) 5-Methoxyindole-3-carboxaldehyde (300 mg, 1.71 mmol) was added in portions over 5 min to a suspension of sodium hydride (82 mg, 2.05 mmol, 60percent dispersion in mineral oil) in DMF (8 mL) stirring under argon. The mixture was stirred for 30 min, methyl iodide (0.13 mL, 2.05 mmol) was added and the mixture was stirred for 1 h. Sodium bicarbonate (10percent, 40 mL) was added and the mixture was extracted with EtOAc (4*). The combined organic layers were washed with sodium bicarbonate (10percent, 2*) and saturated NaCl, dried (MgSO4), filtered and evaporated. Column chromatography of the crude product (50:50 EtOAc:hexanes) afforded 43 (320 mg, 99percent) as a light yellow solid; Rf=0.35 (50:50 EtOAc:hexanes); mp=130-132° C.; lit mp=132-133° C.53; 1H NMR (CDCl3): δ 9.95 (s, 1H), 7.79 (d, 1H, J=2.4 Hz), 7.62 (s, 1H), 7.25 (d, J=8.8 Hz), 6.96 (dd, 1H, J=2.4 and 8.9 Hz), 3.90 (s, 3H), 3.85 (s, 3H). |
1.03 g | Stage #1: With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.166667 h; Inert atmosphere Stage #2: at 0 - 40℃; for 0.5 h; Inert atmosphere |
5-methoxy-indole 22 (1.78 g, 9.40 mmol) was added gradually and under dry argon to a suspension of NaH (0.564 g of a 60percent dispersion, 14.11 mmol) in dry DMF (4 mL). The suspension was stirred at room temperature for 10 min and cooled to 0 °C, and MeI (0.81 g, 5.71 mmol) was added over 5 min. The solution was then heated at 40 °C for 30 min, cooled, poured into cold water. The mixture was extracted with EtOAc (2× 150 mL), dried and evaporated. The residue was used without purification (1.03 g, 95percent). 1H NMR (300 MHz, DMSO-d6): δ (ppm) 9.72 (s, 1H), 8.45 (s, 1H), 7.82 (d, J = 9.1 Hz, 1H), 7.37 (d, J = 9.1 Hz, 1H), 3.93 (s, 3H), 3.91 (s, 3H); MS (ESI) m/z: 190.1 [M+H]+. |
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