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CAS No. : | 1075-35-0 | MDL No. : | MFCD00005619 |
Formula : | C9H8ClN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WUVWAXJXPRYUME-UHFFFAOYSA-N |
M.W : | 165.62 | Pubchem ID : | 70636 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.11 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 48.27 |
TPSA : | 15.79 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) : | -5.12 cm/s |
Log Po/w (iLOGP) : | 2.03 |
Log Po/w (XLOGP3) : | 3.08 |
Log Po/w (WLOGP) : | 3.13 |
Log Po/w (MLOGP) : | 2.46 |
Log Po/w (SILICOS-IT) : | 3.63 |
Consensus Log Po/w : | 2.87 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.41 |
Solubility : | 0.064 mg/ml ; 0.000387 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.08 |
Solubility : | 0.138 mg/ml ; 0.000834 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.28 |
Solubility : | 0.00873 mg/ml ; 0.0000527 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.24 |
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% | With carbon monoxide In toluene at 120℃; for 5 h; | EXAMPLE 10 Synthesis of 5-chloro-2-methylindole In a stainless steel autoclave having an internal volume of 100 mL, 1.09 g (5.1 mmol) of 5-chloro-2-nitrophenylacetone, 72 mg (4 mol percent) of cyclopentadienyidicarbonyliron (dimer) and 40 g of toluene were placed under nitrogen atmosphere. After the atmosphere inside of the reactor was substituted by nitrogen gas (10 kgf/cm2) three times, carbon monoxide gas was injected (30 kgf/cm2), and the resulting mixture was reacted at a temperature of 120 C. for 5 hours. After cooling, the reaction solution was subjected to quantitative analysis with liquid chromatography. As a result of it, it was confirmed that 5-chloro-2-nitrophenylacetone was completely disappeared. Thereafter, post-treatment was conducted, and the main product was isolated with silica gel chromatography to obtain 0.79 g (yield 94.0percent) of 6-fluoro-2-methylindole. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With triphenylphosphine In diphenylether at 260℃; for 1 h; | General procedure: In a 50 ml round bottom flask containing magnetic stir bar was charged with o-nitro benzaldehydes (2 mmol), phosphorane (2.2 mmol), triphenyl phosphine (4.6 mmol) and diphenyl ether (10 mL) and heated at 260 oC for 1 h. The reaction mass was then cooled to room temperature and poured on silica column. Products were isolated by eluting with petrolium ether to 3:1 pet ether: ethyl acetate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | 0.96 g of POCl3 was added drop wise to a solution of 2-methyl-5-chloroindole (1.0 g) in 20 mL of DMF), at 10 C. The mixture was stirred at 50 C. for 1 hr, cooled and diluted with saturated NaHCO3. The suspension was heated at 60 C. for 15 min, cooled, and the precipitates of 2-methyl-5-chloroindole-3-carboxaldehyde were filtered.Yield 1.14 g (99%). An analytical sample was crystallized from EtOH. | |
92% | General procedure: POCl3 (1.73 mL, 18.6 mmol) was slowly added dropwise into stirred and ice-cooled DMF (5.0 mL). The reaction mixture was stirred at 1-5 C for 20 min, then a solution of corresponding substituted 2-methylindole 6 (15.5 mmol) in DMF (5.0 mL) was slowly added. The resulting reaction mixture was slowly warmed to 35 C and kept at this temperature for 40 min. It was then allowed to cool down to room temperature. To this mixture, ice (~10 g) was added followed by 5 M NaOH solution (31 mL, 155 mmol). The reaction mixture was heated at 95 C for 30 min, and then it was allowed to cool down to room temperature. To this mixture, ice (~10 g) was again added, and the resulting reaction mixture was stirred for 30 min. The desired product was collected by filtration and washed several times with water. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | With trichlorophosphate; In ethanol; at 50℃; for 8.5h;Heating / reflux; | A mixture of 5-chloro-2-methylindole (30.1 g; 0.18 mole) and 1-acetyl-imidazolidine-2-one (24 g; 0.18 mole) was added to phosphorous oxychloride (178 ml) and heated to 50 C. After 5 hours, phosphorous oxychloride was evaporated. The residue was treated with ethanol (250 ml) cautiously and maintained at reflux for 3.5 hours. The mixture was concentrated under reduced pressure to half of the orignal volume to obtain a precipitate, which was collected on a filter. The crystalline residue was treated with water, washed with ethylacetate, treated with 2N sodium hydroxide to pH 11 and stirred overnight. The precipitate was filtered, washed with water and t-butylmethylether and dried to give product (10.9 g, 26%), m.p. 213 C. [0467] 1H-NMR(DMSO): d 2.5 (s, 3H, CH-31), 3.55 (s, 4H, 2×CH-2), 6.30 (b, 1H, imidazolin), 7.04 (d, 1H 8.00 (s, 1H, H-4), 11.57 (b, 1H, NH-indol); MS (Ei 70 eV) m/Z 233M+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | To a 250 mL round bottom flask under an atmosphere of nitrogen was added <strong>[1075-35-0]5-chloro-2-methylindole</strong> (5.0 g, 30.2 mmol, 1.0 equiv) and 100 mL THF. The resulting solution was cooled to -78 C. in a dry ice/acetone bath, and n-butyllithium (21 mL of 1.51M solution, 31.72 mmol, 1.05 equiv) was added dropwise over 30 minutes. This was allowed to stir at -78 C. for 30 minutes, at which point zinc chloride (4.12 g, 30.2 mmol, 1.0 equiv) was added as a solution in 5 mL THF dropwise. The resulting mixture was allowed to warm to room temperature. Methyl bromoacetate (2.78 mL, 30.2 mmol, 1.0 equiv) was then added and the reaction allowed to stir fro 24 hours. The reaction mixture was then poured into 500 mL saturated aqueous ammonium chloride and extracted with three 100 mL portions of ethyl acetate. The combined organic layers were washed with water and brine and dried over MgSO4. Filtration and concentration in vacuo gave the crude material which was purified by silica gel chromatography to give the desired product as a yellow oil (4.53 g, 63%). 1H NMR (400 MHz, CHLOROFORM-d) δ 2.35 (s, 3H) 3.64 (s, 2H) 3.68 (s, 3H) 6.99-7.07 (m, 1H) 7.09-7.14 (m, 1H) 7.46 (d, J=2.0 Hz, 1H) 7.95 (br. s., 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With triethylsilane; trifluoroacetic acid; In dichloromethane; | To a solution of <strong>[1075-35-0]5-chloro-2-methylindole</strong> (0.86 g, 5.2 mmol) and 4-(3-Oxo-propyl)-benzoic acid methyl ester (1.0 g, 5.2 mmol) in methylene chloride (50 mL), was added TFA (1.78 g, 15.6 mmol), followed by triethylsilane (1.81 g, 15.6 mmol). The reaction mixture was stirred overnight, quenched with sat. NaHCO3 solution (50 mL), and the organic layer was washed with sat. NaHCO3 solution, water, brine, and dried (Na2SO4). Solvent was removed under reduced pressure, and the residue was purified by flash column chromatography with 10-20% EtOAc/hexanes to yield the desired product in 94% (1.67 g) yield. |
94% | With triethylsilane; trifluoroacetic acid; In dichloromethane; | To a solution of <strong>[1075-35-0]5-chloro-2-methylindole</strong> (0.86 g, 5.2 mmol) and 4-(3-oxo-propyl)- benzoic acid methyl ester (1.Og, 5.2 mmol) in methylene chloride (50 mL), was added TFA (1.78 g, 15.6 mmol), followed by triethylsilane (1.81 g, 15.6 mmol). The reaction mixture was stirred overnight, quenched with sat. NaHCO3 solution (50 mL), and the organic layer was washed with sat. NaHCO3 solution, water, brine, and dried (Na2SO4). The solvent was removed under reduced pressure, and the residue was purified by flash column chromatography with 10-20% EtOAc/hexanes to yield the desired product (1.67g) in 94% yield. |
94% | With triethylsilane; trifluoroacetic acid; In dichloromethane; | To a solution of <strong>[1075-35-0]5-chloro-2-methylindole</strong> (0.86 g, 5.2 mmol) and 4-(3-oxo-propyl)-benzoic acid methyl ester (1.0 g, 5.2 mmol) in methylene chloride (50 mL), was added TFA (1.78 g, 15.6 mmol), followed by triethylsilane (1.81 g, 15.6 mmol). The reaction mixture was stirred overnight, quenched with sat. NaHCO3 solution (50 mL), and the organic layer was washed with sat. NaHCO3 solution, water, brine, and dried (Na2SO4). Solvent was removed under reduced pressure, and the residue was purified by flash column chromatography with 10-20% EtOAc/hexanes to yield the desired product in 94% (1.67 g) yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With triethylsilane; trifluoroacetic acid; In dichloromethane; water; at 20℃; for 48h; | To the above product (1.0 eq) and 5-chloro-2-methyl indole (1.0 eq) in CH2Cl2 (0.12 M) was added triethylsilane (3.0 eq) followed by trifluoroacetic acid (3.0 eq). After being stirred overnight at room temperature, added water and trifluroacetic acid (1.0 eq) to the reaction mixture, stirred at room temperature for two days, diluted with CH2Cl2, washed with 1N NaOH, water, brine, dried over sodium sulfate. Trituration of the material with CH2Cl2 and hexanes afforded the C3 alkylated indole in 92% yield |
92% | To the above product (1.0 eq) and 5-chloro-2-methyl indole (1.0 eq) in CH2CI2 (0.12 M) was added triethylsilane (3.0 eq) followed by trifluoroacetic acid (3.0 eq). After being stirred overnight at room temperature, water and trifluroacetic acid (1.0 eq) were added to the reaction mixture, which was stirred at room temperature for two days, diluted with CH2CI2, washed with 1N NaOH, water, and brine, and dried over sodium sulfate. Trituration of the material with CH2CI2 and hexanes afforded the C3 alkylated indole in 92% yield | |
92% | With triethylsilane; trifluoroacetic acid; In dichloromethane; at 20℃; | To the above product (1.0 eq) and 5-chloro-2-methyl indole (1.0 eq) in CH2Cl2 (0.12 M) was added triethylsilane (3.0 eq) followed by trifluoroacetic acid (3.0 eq). After being stirred overnight at room temperature, added water and trifluroacetic acid (1.0 eq) to the reaction mixture, stirred at room temperature for two days, diluted with CH2Cl2, washed with 1N NaOH, water, brine, dried over sodium sulfate. Trituration of the material with CH2Cl2 and hexanes afforded the C3 alkylated indole in 92% yield |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With iodine; p-Chlorothiophenol; In ethanol; for 1.16667h; | A solution of iodine (14 g) was added dropwise over 10 mins to a solution of the 5-chloro- 2-methyl indole (8.3 g) and 4-chlorothiophenol [(8] g) in ethanol (250 ml) and stirred for 1 hour. The mixture was concentrated in vacuo and the residue was treated with diethyl ether to give the sub-title compound as an off white solid (9.9 g) MS: APCI (+ve): 291 [M+H] [+] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With 2-(Dimethylamino)pyridine; In tetrahydrofuran; at 0 - 20℃; for 18.5h; | A. 5-Chloro-2-methyl-indole-1-carboxylic acid tert-butyl ester. A solution containing <strong>[1075-35-0]5-chloro-2-methylindole</strong> (4.0 g, 24.1 mmol) and DMAP (295 mg, 2.42 mmol) in anhydrous THF (100 ML) is cooled to 0 C. A solution containing (Boc)2O (5.27 g, 24.1 mmol) in anhydrous THF (100 ML) is then added over a 20 min period.The reaction mixture is stirred for 2 h at 0 C. and then at ambient temperature for 16 hours.The reaction mixture is concentrated and the crude residue is purified by flash silica gel chromatography (2% EtOAc/hexane to 5% EtOAc/hexane) to provide 5.2 g (81%) of title compound as a pale yellow solid. 1H NMR (300 MHz, CDCl3) δ1.67 (s, 9H), 2.57 (s, 3H), 6.24 (t, J=0.9 Hz, 1H), 7.16 (dd, J=8.8, 2.1 Hz, 1H), 7.38 (d, J=2.1 Hz, 1H), 8.01 (d, J=8.8 Hz, 1H) ppm; MS (EI): m/z 265 (M+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tin(IV) chloride; In dichloromethane; at 20℃; for 6h; | A mixture of <strong>[1075-35-0]5-chloro-2-methylindole</strong> (248 mg, 0.5 mmol) and acetyl chloride (0.045 mL, 0.6 mmol) in methylene chloride is treated with a 1.0 M solution of tin tetrachloride in methylene chloride (0.55 μL, 0.55 mmol), shaken at room temperature for 6 h, quenched with saturated NaHCO3 and extracted with ethyl acetate. The extracts are combined and concentrated in vacuo. The resultant residue and phenylsulfonyl chloride (0.095 mL, 0.75 mmol) are dissolved in THF, treated with NaH (60 mg, 1.5 mmol) at room temperature, shaken for 6 h, quenched with saturated NaHCO3 and extracted with ethyl acetate. The extracts are combined and concentrated in vacuo to give a residue. This residue is suspended in isopropanol, treated sequentially with aminoguanidine bicarbonate (100 mg, 0.5 mmol) and concentrated HCl (50 μL), heated at 80 C. for 4 h, cooled to room temperature and concentrated in vacuo. This resultant residue is purified by HPLC to afford the title product, 10 mg (5% yield), identified by HPLC and mass spectral analyses, (M+H) 404; retention time 4.72 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.98 g (63%) | With triethylsilane; trifluoroacetic acid; In dichloromethane; ethyl acetate; | EXAMPLE 88 4-[(1-benzhydryl-5-chloro-2-methyl-1H-indol-3-yl)methyl]benzoic acid Step 1 To an ice-cold (0 C.) solution of trifluoroacetic acid (1.7 ml, 15 mmol) and triethylsilane (4.8 ml, 30 mmol) in CH2Cl2 (20 mL) was added a solution of <strong>[1075-35-0]5-chloro-2-methylindole</strong> (1.66 g, 10 mmol) and methyl 4-formylbenzoate (1.8 g, 11 mmol) in CH2Cl2 (50 mL) over a period of 5 min. The resulting homogeneous solution was stirred at 0 C. for 1 h and rt for 2 h, at which time EtOAc (150 mL) and aqueous sodium bicarbonate (to pH=8) was added. The organic layer was washed with water and brine, dried over MgSO4 and concentrated. Flash chromatography (Hex/EtOAc, 4/1) gave 1.98 g (63%) of desired intermediate as a light-tan solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3,3-Dimethyl-dihydro-furan-2,5-dione (7.8 mmol, 1.0 g), 5-chloro-2- methylindole (13.8 mmol, 2.28 g), and AlCl3 (9.0 mmol, 1.2 g) were stirred in 100 mL DCE overnight at 65 C. The reaction was cooled and quenched with 10 mL water. The resultant precipitate was filtered and washed with a small amount of DCE giving 1.06 g of the sub-titled compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With phosphoric acid; In acetic acid; | a. A mixture consisting of 100 gm (0.6 mol) of 5-chloro-2-methyl-indole, 100 gm (0.65 mol) of <strong>[40064-34-4]4-piperidone monohydrate hydrochloride</strong>, 900 ml of glacial acetic acid and 450 ml of 4 N phosphoric acid was heated for 2 hours at 80C. Thereafter, the reaction mixture was cooled and then poured into a mixture of ice and ammonia, and the resulting mixture was extracted with ethyl acetate. The organic extract solution was washed with water, dried and evaporated, and the residue was recrystallized from methanol, yielding 108 gm (73% of theory) of 4-(5'-chloro-2'-methyl-3'-indolyl)-1,2,5,6-tetrahydropyridine, m.p. 208-210C. | |
With phosphoric acid; In acetic acid; at 80℃; | General procedure: 2-Methyl-1H-indole derivatives (0.5-6 mmol, 1 equiv) were stirred at 80 C in acetic acid (2 mL/1 mmol), <strong>[40064-34-4]4-piperidone hydrochloride hydrate</strong> (1.5-18 mmol, 3 equiv) and 1 M phosphoric acid (1 mL/1 mmol) were added. After 1-2 h, the mixture was poured into ice/ammonia, and extracted with ethyl acetate (3 x 25 mL). The combined organic layers were washed with water and brine, dried, and evaporated in vacuo to give the title compounds. The crude products were purified by silica gel column chromatography (ethylacetate-methanol, gradient) and most of them were converted to the corresponding salts by dissolving the free base in methanol or ethanol and adding one equivalent of oxalic acid or ethanolic HCl solution. The solvent was removed and azeotroped with absolute ethanol in vacuo followed by recrystallization from appropriate solvents. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With carbon monoxide;cyclopentadienyl iron(II) dicarbonyl dimer; In toluene; at 120℃; for 5h; | EXAMPLE 10 Synthesis of 5-chloro-2-methylindole In a stainless steel autoclave having an internal volume of 100 mL, 1.09 g (5.1 mmol) of 5-chloro-2-nitrophenylacetone, 72 mg (4 mol %) of cyclopentadienyidicarbonyliron (dimer) and 40 g of toluene were placed under nitrogen atmosphere. After the atmosphere inside of the reactor was substituted by nitrogen gas (10 kgf/cm2) three times, carbon monoxide gas was injected (30 kgf/cm2), and the resulting mixture was reacted at a temperature of 120 C. for 5 hours. After cooling, the reaction solution was subjected to quantitative analysis with liquid chromatography. As a result of it, it was confirmed that 5-chloro-2-nitrophenylacetone was completely disappeared. Thereafter, post-treatment was conducted, and the main product was isolated with silica gel chromatography to obtain 0.79 g (yield 94.0%) of 6-fluoro-2-methylindole. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In N,N-dimethyl-formamide; at 45℃; | Preparation 1a (δ-chloro^-methylindol-i-yljacetic acid methyl esterA mixture of 5-chloro-2-methyl-1 H-indole (1.0 g), bromoacetic acid methyl ester (0.83 mL), potassium carbonate (2.5 g) and λ/,/V-dimethylformamide (7.0 ml_) was stirred at 450C overnight. The reaction mixture was diluted with 1.0 M aqueous hydrochloric acid and the resulting precipitate collected by filtration and dried to afford (5-chloro-2-methyl-indol-1-yl)acetic acid methyl ester, 1.3 g.1H NMR (DMSO-d6): δ 2.30 (d, J = 0.9 Hz, 3H), 3.70 (s, 3H), 5.10 (s, 2H), 6.25 (t, J = 0.9 Hz, 1H), 7.05 (dd, J = 1.9, 8.7 Hz, 1H), 7.40 (d, J = 8.7 Hz, 1H), 7.45 (d, J = 1.9 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With sodium cyanoborohydride; In acetic acid; at 20℃; for 16h; | (a) (RS)-5-Chloro-2-methyl-2,3-dihydro-1H-indole To a solution of <strong>[1075-35-0]5-chloro-2-methylindole</strong> (1.00 g, 6.04 mmol) in acetic acid (7 ml) was added portionwise sodium cyanoborohydride (0.76 g, 12.1 mmol) and the reaction mixture was stirred at room temperature for 16 hours. The resulting solution was diluted with ethyl acetate and washed sequentially with water and with 5 N aq. sodium hydroxide solution. The organic phase was dried over sodium sulphate and concentrated in vacuo. The residue was purified by chromatography on silica gel (eluant: heptane/ethyl acetate gradient) to yield the title compound as a colourless oil (1.00 g, 100%); MS (ISP): 170.2 ([{37Cl}M+H]+), 168.3 ([{35Cl}M+H]+). |
100% | With sodium cyanoborohydride; acetic acid; at 20℃; for 16h; | To a solution of <strong>[1075-35-0]5-chloro-2-methylindole</strong> (1.00 g, 6.04 mmol) in acetic acid(7 ml) was added portionwise sodium cyanoborohydride (0.76 g, 12.1 mmol) and the reaction mixture was stirred at room temperature for 16 hours. The resulting solution was diluted with ethyl acetate and washed sequentially with water and with 5 N aq. sodium hydroxide solution. The organic phase was dried over sodium sulphate and concentrated in vacuo. The residue was purified by chromatography on silica gel (eluant: <n="22"/>heptane/ ethyl acetate gradient) to yield the title compound as a colourless oil (1.00 g, 100%); MS (ISP): 170.2 ( [{37Cl}M+H]+); 168.3 ([{35C1}M+H]+). |
With 1,1,1,3',3',3'-hexafluoro-propanol; (RuBF4((S,S)-N-Me-Msdpen)(p-cymene)); hydrogen; at 30℃; under 37503.8 Torr; for 20h;Autoclave; | 10305] A 50 mE autoclave was charged with 6.3 mg (0.01 mmol, S/C100) of RuBF4((S,S)-N-Me-Msdpen) (p-cymene) obtained in Synthesis Example 18 serving as a catalyst, 0.16 12 g (1 mmol) of <strong>[1075-35-0]5-chloro-2-methylindole</strong>, and 1.2 mE of HFIP, and the reaction was allowed to proceed at30 C. for 20 hours under a hydrogen pressure of 5 MPa. The conversion and the optical purity determined by GC analysis were 99.1% cony. (conversion) and 94.3% cc (optical purity). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5-Chloro-2-methylindole (0.16 g) and 4,8-dichloroquinoline (0.2 g) were suspended in NMP (0.5 ml) and heated in a microwave at [100W,] 140 C for 60 minutes. When reaction was complete THF (5 ml) was added followed by sodium hydride 60% dispersion in oil (0.12 g). After 30 mins a solution of methyl bromoacetate (0.2 ml) in THF [(1] ml) was added and the mixture stirred at room temperature for 24 hours. Ethyl acetate and saturated brine solution were added, the aqueous phase was separated and extracted with ethyl acetate. The combined organic solution was evaporated to leave a residue which was purified by silica gel chromatography using dichloromethane/ethyl acetate (9: 1) to provide the sub-title product as an oil. (120 mg). MS: APCI (+ve): 399/401/403 [[M+H] +] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | To a 0 C. solution of 5-chloro-2-methyl-indole (0.100 g, 0.6 mmol) in DMSO (6 mL) was added portionwise potassium hydroxide (0.33 g, 6 mmol). The resulting solution was stirred at room temperature for 15 minutes. To this was added methyl-2-bromo propionate (0.1 mL, 0.9 mmol) in a single portion. The reaction mixture was stirred at room temperature for 16 h. The solution was cooled to 0 C. and quenched with water (20 mL). The mixture was extracted with CH2Cl2 (50 mL). This solution was washed with a saturated solution of ammonium chloride (2×20 mL), brine (200 mL), and dried over sodium sulfate. The solution was concentrated and the residue was purified via silica gel chromatography using 15-40% CH2Cl2 in hexanes to obtain the methyl ester as a clear oil (0.05 g, 0.21 mmol, 35% yield). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA), m/z: M+1 obs=238; tR=3.03 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 4Synthesis of CBX0024-(2-(5-chloro-2-methyl-lH-indol-l-yl)ethyl)morpholine[0157] To a solution of 2-chloroethylmorpholine HC1 (100 mg, 0.60 mmol) in 0.3 mL DMSO was added pulverized KOH (102 mg, 1.81 mmol), then after 10 min, a solution of 5- chloro-2-methylindole (134 mg, 0.72 mmol) in 0.2 mL DMSO was added and the reaction stirred at room temperature overnight. Additional 2-chloroethylmorpholine (22 mg, 0.12 mmol) and KOH (17 mg, 0.3 mmol) added and stirred overnight. The reaction mixture was partitioned between ¾0 and toluene, and the organic extract washed two times with ¾0, dried over MgS04, filtered, and concentrated in vacuo. The crude product was purified via silica gel chromatography using a gradient from 0 to 5% MeOH in (¾(¾ to give a final yield of 154 mg (0.55 mmol). XH NMR (500 MHz, CDC13, δ): 2.47 (s, 3H), 2.48-2.57 (m, 4H), 2.63 (t, J = 7.2 Hz, 2H), 3.73 (t, J = 4.4 Hz, 4H), 4.16 (t, J = 7.2 Hz, 2H), 6.20 (s, 1H), 7.1 1 (dd, J = 8.6 Hz, 1.7 Hz, 1H), 7.19 (d, J = 8.6 Hz, 1H), 7.50 (d, J = 1.5 Hz, 1H). 13C NMR (500 MHz, CDC13, δ): 12.88, 41.23, 54.13, 57.86, 66.95, 99.88, 109.78, 1 19.15, 120.64, 124.97, 129.18, 134.99, 138.03. MS m/z 279.3 [M + H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | General procedure: 5-Chloro-2-methyl-1H-indole (0.9-5.1 mmol, 1 equiv) was dissolved in 2-4mL anhydrous dimethylformamide at 0 C and 60% NaH (1.1-6.2 mmol, 1.2 equiv) was added, The mixture was stirred under N2 until evolution of H2 gas ceased (approx. 30 min). Iodoethane, iodomethane or 1-iodopropane (1.1-6.2 mmol, 1.2 equiv) was added and the mixture was allowed to stir for 12 h. Brine was added and the reaction mixture was extracted with ethyl acetate. The organic portion was dried (MgSO4) and the solvent was removed under reduced pressure. The residue was purified by flash chromatography on silica gel (ethyl acetate/methanol, gradient) to give the title compounds |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | General procedure: 5-Chloro-2-methyl-1H-indole (0.9-5.1 mmol, 1 equiv) was dissolved in 2-4mL anhydrous dimethylformamide at 0 C and 60% NaH (1.1-6.2 mmol, 1.2 equiv) was added, The mixture was stirred under N2 until evolution of H2 gas ceased (approx. 30 min). Iodoethane, iodomethane or 1-iodopropane (1.1-6.2 mmol, 1.2 equiv) was added and the mixture was allowed to stir for 12 h. Brine was added and the reaction mixture was extracted with ethyl acetate. The organic portion was dried (MgSO4) and the solvent was removed under reduced pressure. The residue was purified by flash chromatography on silica gel (ethyl acetate/methanol, gradient) to give the title compounds |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | General procedure: 5-Chloro-2-methyl-1H-indole (0.9-5.1 mmol, 1 equiv) was dissolved in 2-4mL anhydrous dimethylformamide at 0 C and 60% NaH (1.1-6.2 mmol, 1.2 equiv) was added, The mixture was stirred under N2 until evolution of H2 gas ceased (approx. 30 min). Iodoethane, iodomethane or 1-iodopropane (1.1-6.2 mmol, 1.2 equiv) was added and the mixture was allowed to stir for 12 h. Brine was added and the reaction mixture was extracted with ethyl acetate. The organic portion was dried (MgSO4) and the solvent was removed under reduced pressure. The residue was purified by flash chromatography on silica gel (ethyl acetate/methanol, gradient) to give the title compounds |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With potassium tert-butylate; In acetone; at 20℃; for 1h; | General procedure: To a stirred solution of substituted indole (4.25 mmol) in acetone (10 mL) was slowly added potassium tert-butanolate (6.38 mmol) and dimethylsulphate (8.5 mmol) or 1-(chloromethyl)-4-fluorobenzene(8.5 mmol) at room temperature for 1 h, then the reaction mixture was poured into saturated aqueous NaHCO3 solution (40 mL), and extracted with CH2Cl2 (3 40 mL), The combined organic layers were dried over anhydrous Na2SO4, and concentrated in vacuo. The crude product was purified by column chromatography (petroleum ether/AcOEt). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | General procedure: Similar to the reported method [19], a mixture of the appropriate indole (0.6 mmol), 1,2-bis-(3,4,5-trimethoxyphenyl)diselenide(0.35 mmol, 0.45 g mixture of 1,2-bis-(3,4,5-trimethoxyphenyl)diselenide with 1,10-selenobis(3,4,5-trimethoxybenzene)), FeCl3 (20 mol%) and I2 (1 mol%, 0.0001 g/mL in CH3CN) was placed into the microwave cavity (closed vessel mode). Microwave irradiation at 150 W was used, the temperature being ramped from 25 C to 80 C. Once 80 C was reached, takingabout 1 min, the reaction mixture was held at this temperature for 30 min while stirring, until complete consumption of the starting material, as monitored by TLC. After the evaporation of the solvent,the residual crude product was purified by column chromatography on silica gel (200-300 mesh) with petroleumether/AcOEt (v/v 5:1) or pure CH2Cl2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With ammonium cerium (IV) nitrate; In methanol; at 25℃; for 0.25h; | General procedure: The substituted indoles 14a-f (1 mmol) and ammonium thiocyanate (1.2 mmol) were dissolved in 4 mL of methanol and treated with cerium (IV) ammonium nitrate (CAN; 2.3 mmol) in methanol (25 mL) at room temperature. The reaction mixture was stirred for 15 min. It was then diluted with water (100 mL) and extracted with ethyl acetate (20 mL x 4). The combined organic layer was washed with water and brine, dried over anhydrous MgSO4, filtered and concentrated to give the crude product, which was purified by column chromatography on silica gel with light petroleum/AcOEt (v/v = 3:1). |
86% | With TiO2/MoS2; In acetonitrile; at 20℃; for 16h;Irradiation; | General procedure: To a solution of indole 1 (0.2 mmol) and ammonium thiocyanate (0.6 mmol) in CH3CN (2 mL) was added TiO2/MoS2 (10: 1, molar ratio, 20 mg). The reaction mixture was stirred under a 14 W CFL irradiation at room temperature for a certain time. After reaction (monitored by TLC), ethyl acetate was added, and the solid catalyst was recovered by centrifugation. The reaction mixture was extracted with ethyl acetate and washed with water. The combined organic phase was then dried over Na2SO4 and concentrated under reduced pressure to give the crude residue, which was purified by column chromatography with petroleum ether/ethyl acetate to afford the pure thiocyanated product 2. The recovered catalyst was then washed with ethanol and deionized water, dried under vacuum, and reused for the next run. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With diphenyl hydrogen phosphate; In 1,2-dichloro-ethane; at 20℃; | General procedure: To a solution of 2-(3-pyrroline-1-yl) arylaldehydes 1 (0.5mmol, 1.0equiv), indoles 2 (0.55mmol, 1.1equiv) in ethylenechloride (5mL) was added diphenyl phosphite (0.1mmol, 0.1equiv). The mixture was stirred at ambient temperature overnight and the reaction was monitored by TLC. After completed, the reaction was concentrated under reduced pressure and purified by flash chromatography on silica gel (petroleum ether: ethyl acetate=20:1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | With potassium tert-butylate; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In toluene; at 110℃; for 22h;Inert atmosphere; | General procedure: t-BuOK (0.66 g, 5.90 mmol) was added to asolution of 2-methylindoles 1a,b (0.98 mmol), benzylhalides 2 or 4 (1.96 mmol), Pd(OAc)2 (0.022 g,0.098 mmol), and Xanthphos (0.057 g, 0.098 mmol) in drytoluene or dioxane (8 ml) in a glass reactor (50 ml) underargon. The reaction mixture was stirred at 110C(for compounds 3a,b) or 130C (for compound 5) for 22 hunder argon. The solvent was removed under reducedpressure and the crude residue was chromatographed onsilica gel using hexane-EtOAc (from 10:1 to 4:1) as eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | To a solution of 5-chloro-2-methyl-1H-indole (1.5 g, 9.1 mmol) in anhydrous THF (20 mL) was added n-BuLi (11 mL, 27.5 mmol, 2.5 M in hexane) dropwise at -70 C under N2. The mixture was stirred at -70 C under N2 for 10 min, followed by adding t-BuOK (18 mL, 18 mmol, 1 M in THF) dropwise. The mixture was allowed to warm to -30 C and stirred for 10 min, then cooled to -70 C. A solution of <strong>[75091-99-5]4-(trifluoromethyl)cyclohexanone</strong> (1.7 g, 10.2 mmol) in anhydrous THF (10 mL) was added dropwise. The mixture was stirred at -70 C under N2 for 2 h. TLC (petroleum ether: ethyl acetate = 5: 1) showed 5-chloro-2-methyl-1H-indole was still remained and two new spot was found. The mixture was quenched with sat. NH4CI solution (10 mL), added H20 (20 mL) and extracted with ethyl acetate (3 X 30 mL). The combined organic layers were dried over anhydrous Na2S04, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with petroleum ether: ethyl acetate = 10: 1-5: 1 to afford 1-((5-chloro-1H-indol-2-yl)methyl)-4-(trifluoromethyl)cyclohexanol (1.2 g, 39%) as a pale yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With sodium iodide; In acetonitrile; at 20℃; for 18h;Irradiation; | General procedure: To a 20 mL glass tube with a stir bar was charged 2-methyl-1H-indole 1a (39.35 mg, 0.3 mmol), diphenyldisulfide 2a (65.50 mg, 0.3 mmol), NaI (0.06 mmol, 9 mg) and MeCN (2 mL). The solution was stirred at room temperature with the irradiation of a 12 W blue LED for 18 h. The solvent was removed under vacuum. The residue was purified by column chromatography over silica gel (petroleum ether/ethyl acetate = 15/1) to give the product 3a (60 mg, 83%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | General procedure: Para substituted chalcones (1 equiv.) (9-16) and malononitrile (1equiv.) were stirred in acetonitrile in the presence of L-proline catalyst at room temperature for half an hour. To this reaction mixture different 2-methyl indole (0.8 equiv.) were added and was heated to 90 C on an oil bath. Reaction mixture was stirred till the completion of reaction as monitored by TLC. Afterwards, the reaction mixture was evaporated to dryness under vacumm and was partitioned between ethyl acetate and water. The combined organiclayer was dried and purified by silica gel column chromatographyto get pure products 17-29 [50]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | General procedure: Para substituted chalcones (1 equiv.) (9-16) and malononitrile (1equiv.) were stirred in acetonitrile in the presence of L-proline catalyst at room temperature for half an hour. To this reaction mixture different 2-methyl indole (0.8 equiv.) were added and was heated to 90 C on an oil bath. Reaction mixture was stirred till the completion of reaction as monitored by TLC. Afterwards, the reaction mixture was evaporated to dryness under vacumm and was partitioned between ethyl acetate and water. The combined organiclayer was dried and purified by silica gel column chromatographyto get pure products 17-29 [50]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With 6,6'-di(phenanthrenyl)phosphoric acid; In dichloromethane; at 20℃; for 15h; | General procedure: Thus, general reaction conditions for aniline oxime are obtained: at room temperature,Indole 2 (0.24 mmol, 1.2 eq) was added to a solution of azobenzene derivative 1 (0.2 mmol, 1.0 eq), CP6 (0.2 mol %) in DCM (4.0 mL),The reaction was stirred at room temperature until TLC showed disappearance of the azobenzene derivative 1, the reaction mixture was concentrated under reduced pressure and purified by silica gel column chromatography eluting with PE/EA to give the desired product 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With sodium periodate; ruthenium(III) chloride trihydrate; In acetonitrile; at 20 - 70℃; for 24h;Schlenk technique; | General procedure: A mixture of indole 1 (0.50 mmol), NaIO4 (107 mg, 0.50 mmol, 1.0 equiv) and RuCl3·3H2O (6.5 mg, 0.025 mmol, 5.0 mol%) in CH3CN (3 mL) was added into aSchlenk flask (25 mL) and stirred at room temperature. The mixture was stirred at 70 C until the reaction was finished. Then the solvent was evaporated underreduced pressure and the residue was purified by column chromatography (petroleum ether/ethyl acetate 10:1 to 5:1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With triphenylphosphine; In diphenylether; at 260℃; for 1h; | General procedure: In a 50 ml round bottom flask containing magnetic stir bar was charged with o-nitro benzaldehydes (2 mmol), phosphorane (2.2 mmol), triphenyl phosphine (4.6 mmol) and diphenyl ether (10 mL) and heated at 260 oC for 1 h. The reaction mass was then cooled to room temperature and poured on silica column. Products were isolated by eluting with petrolium ether to 3:1 pet ether: ethyl acetate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In chloroform; water; at 0 - 20℃; for 17.0h; | To a solution of 5-chloro-2-methyl-1H-indole (5.00 g, 30.3 mmol) and TEBAC (0.60 g, 0.300 mmol) in CHCl3 (150 ml) was added, at 0 C., NaOH in water. The mixture was stirred at 0 C. for 3 h and then at RT for 14 h. The reaction mixture was then added gradually to ice-water and extracted with chloroform. The organic phase was washed with water, dried over Na2SO4 and concentrated on a rotary evaporator. The residue was purified by column chromatography purification with a hexane/ethyl acetate gradient as eluent. MH+: 212; 1H-NMR (400 MHz, CDCl3): delta 2.78 (s, 3H), 7.58-7.61 (dd, J=2.32 & 9.0 Hz, 1H), 7.68-7.69 (d, J=2.28 Hz, 1H), 7.91-7.94 (d, J=9.0 Hz, 1H), 8.01 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With ammonium iodide; 1,10-Phenanthroline; acetic acid; In 1,4-dioxane; at 100℃; for 6h;Sealed tube; | General procedure: A Schlenk tube (25 mL) was charged with indole (0.3 mmol), ethyl arylsulfinate (0.4 mmol), NH4I (20 mol%), and 1,10-phenanthroline (10 mol%). 1,4-Dioxane (2 mL) and HOAc (0.5 mL) were added under air atmosphere, the tube was sealed and heated in an oil bath at 100 C for 6 h. The crude mixture was allowed to cool to room temperature. Then, ethyl acetate and saturated aq. solution of NaCl (5 mL) were added and the layers separated. The aqueous phase was washed three times with ethyl acetate (5 mL x 3). The combined organic layers were dried over anhydrous MgSO4 and concentrated in vacuo. The crude was purified by flash column chromatography with Al2O3 (petroleum ether/EtOAc) giving desired products 3a-z and 4a-t. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 20℃; for 3h; | General procedure: General procedure for C3-dialkylation of indoles. In a flame dried flask, the imidate (2.5 equiv)was dissolved in anhydrous DCE (0.3 M) followed by the addition of the indole (1.0 equiv). To thissolution freshly distilled TMSOTf (1.0 equiv) was added and the resulting mixture was stirred atroom temp. or heated to reflux for 3 h. After cooling to room temperature, the reaction mixture wasquenched with 10 mL 1MNaOH. The organic layer was separated and the aqueous layer was extractedwith DCM (3 5 mL). The combined organic layers were dried over sodium sulfate, filtered andconcentrated. The residue was purified by silica gel chromatography using the listed solvent system. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With sodium carbonate; In acetonitrile; at 20 - 120℃; for 24h;Schlenk technique; | General procedure: A mixture of indole 1 (0.50 mmol), Na2CO3 (10.6 mg, 0.10 mmol, 20 mol%) and diaryl carboxylate 2 (0.60 mmol, 1.2 equiv) in CH3CN (3 mL) was added into a Schlenk flask (25 mL) and stirred at room temperature. The mixture was stirred at 120 C until the reaction was finished. Then the solvent was evaporated under reduced pressure and the residue was purified by column chromatography (petroleum ether/ethyl acetate 50:1 to 10:1). |
Tags: 1075-35-0 synthesis path| 1075-35-0 SDS| 1075-35-0 COA| 1075-35-0 purity| 1075-35-0 application| 1075-35-0 NMR| 1075-35-0 COA| 1075-35-0 structure
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