* 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.
Reference：
[1] Australian Journal of Chemistry, 1983, vol. 36, # 1, p. 135 - 147
2
[ 4027-57-0 ]
[ 74-88-4 ]
[ 5744-51-4 ]
Yield
Reaction Conditions
Operation in experiment
85%
Stage #1: With sodium hydride In tetrahydrofuran at 50℃; for 1 h; Cooling with ice Stage #2: at 50℃; for 2 h;
Ethyl 5-methyl-1-hydro-pyrazolecarboxylate (30.8 g, 200 mmol) was dissolved in 200 mL of dry tetrahydrofuran solution. Sodium hydride (4.8 g, 200 mmol) was slowly added under ice-cooling and sodium hydride was added completely. After the temperature was raised to 50°C, the mixture was stirred for 1 hour and cooled to room temperature. Methyl iodide (28.2 g, 200 mmol) was then dissolved in 100 mL of tetrahydrofuran and slowly added dropwise to the reaction. The addition was complete and heating to 50°C was continued for 2 hours. After the reaction is complete, cool to room temperature, remove tetrahydrofuran under reduced pressure, then add 100 mL of water, extract with ethyl acetate (100 mL x 3), combine the organic layers, dry, and remove the ethyl acetate under reduced pressure to give 5-methyl-1-carbonitrile. Ethyl 2-pyrazolecarboxylate 26.6 g, 85percent.Lithium aluminum hydride (3.8 g, 100 mmol) was added to a dry three-necked flask, 200 mL of dry tetrahydrofuran, and then ethyl 5-methyl-1-methyl-pyrazolecarboxylate (16.8 g, 100 mmol) was dissolved in 100 mL of dry. Tetrahydrofuran was slowly added dropwise to the three-necked flask, and stirring was continued for 4 hours after completion of the addition. After the reduction is completed, absolute ethanol is added dropwise to remove the remaining lithium tetrahydroaluminum, the tetrahydrofuran is removed under reduced pressure, 500 mL of methanol is added, the pH is adjusted to neutral, the mixture is heated to reflux for 6 hours, and the filtrate is filtrated. The filtrate is concentrated and dissolved in 100 mL of dichloromethane. And washed twice with 50 mL of saturated aqueous sodium chloride, and the organic layer was dried and concentrated to give 5-methyl-1-methyl-pyrazolemethanol 8.8 g, 70percent.5-methyl-1-carbonitrileThe base-pyrazole methanol (6.3 g, 50 mmol) was dissolved in 20 mL of methylene chloride. Thionyl chloride (6 g, 50 mmol) was slowly added dropwise. After the addition was complete, stirring was continued for 2 hours. After the reaction was complete, saturated sodium bicarbonate was added slowly. The aqueous solution was adjusted to pH neutral and then extracted with 200 mL of dichloromethane. The organic layers were combined, dried and concentrated to give 3-chloromethyl-1-methyl-5-methylpyrazole (6.5 g, 90percent).In a 50 mL round bottom flask was added 3-chloromethyl-1-methyl-5-methylpyrazole (1.44 g, 10 mmol) and N-(2,4,6-trimethylphenyl)imidazole (1.86 g) (10 mmol), 20 mL of acetonitrile, and the mixture was heated under reflux for 6 hours, cooled to room temperature, and the solvent was distilled off under reduced pressure. The obtained solid was dissolved in water and filtered. The filtrate was saturated with aqueous solution of ammonium hexafluorophosphate, and the solid precipitated and was dried to give 3.8. g imidazolium salt ligand (HL1PF6), yield 88percent.
Reference：
[1] Patent: CN106478734, 2017, A, . Location in patent: Paragraph 0027; 0028; 0029
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 5, p. 2180 - 2194
[3] Medicinal Chemistry Research, 2012, vol. 21, # 10, p. 2772 - 2778,7
3
[ 4027-57-0 ]
[ 74-88-4 ]
[ 5744-51-4 ]
Reference：
[1] European Journal of Inorganic Chemistry, 2011, # 11, p. 1768 - 1775
4
[ 615-79-2 ]
[ 60-34-4 ]
[ 5744-51-4 ]
Reference：
[1] Organic Letters, 2011, vol. 13, # 6, p. 1436 - 1439
[2] Patent: US5606051, 1997, A,
Reference：
[1] Journal of Organic Chemistry, 2003, vol. 68, # 15, p. 5977 - 5982
8
[ 615-79-2 ]
[ 60-34-4 ]
[ 5744-51-4 ]
[ 5744-40-1 ]
Reference：
[1] Australian Journal of Chemistry, 1983, vol. 36, # 1, p. 135 - 147
9
[ 615-79-2 ]
[ 5744-51-4 ]
Reference：
[1] Journal of Medicinal Chemistry, 2015, vol. 58, # 5, p. 2180 - 2194
10
[ 64-17-5 ]
[ 7339-53-9 ]
[ 135351-18-7 ]
[ 5744-51-4 ]
[ 5744-40-1 ]
Reference：
[1] Journal of Heterocyclic Chemistry, 1999, vol. 36, # 1, p. 217 - 220
11
[ 98790-58-0 ]
[ 60-34-4 ]
[ 5744-51-4 ]
[ 5744-40-1 ]
Reference：
[1] Journal of Organic Chemistry, 2003, vol. 68, # 15, p. 5977 - 5982
12
[ 615-79-2 ]
[ 60-34-4 ]
[ 5744-51-4 ]
[ 5744-40-1 ]
Reference：
[1] Australian Journal of Chemistry, 1983, vol. 36, # 1, p. 135 - 147
13
[ 64-17-5 ]
[ 7339-53-9 ]
[ 135351-18-7 ]
[ 5744-51-4 ]
[ 5744-40-1 ]
Reference：
[1] Journal of Heterocyclic Chemistry, 1999, vol. 36, # 1, p. 217 - 220
14
[ 5744-51-4 ]
[ 153912-60-8 ]
Yield
Reaction Conditions
Operation in experiment
70%
With lithium aluminium tetrahydride In tetrahydrofuran for 4 h;
Ethyl 5-methyl-1-hydro-pyrazolecarboxylate (30.8 g, 200 mmol) was dissolved in 200 mL of dry tetrahydrofuran solution. Sodium hydride (4.8 g, 200 mmol) was slowly added under ice-cooling and sodium hydride was added completely. After the temperature was raised to 50°C, the mixture was stirred for 1 hour and cooled to room temperature. Methyl iodide (28.2 g, 200 mmol) was then dissolved in 100 mL of tetrahydrofuran and slowly added dropwise to the reaction. The addition was complete and heating to 50°C was continued for 2 hours. After the reaction is complete, cool to room temperature, remove tetrahydrofuran under reduced pressure, then add 100 mL of water, extract with ethyl acetate (100 mL x 3), combine the organic layers, dry, and remove the ethyl acetate under reduced pressure to give 5-methyl-1-carbonitrile. Ethyl 2-pyrazolecarboxylate 26.6 g, 85percent.Lithium aluminum hydride (3.8 g, 100 mmol) was added to a dry three-necked flask, 200 mL of dry tetrahydrofuran, and then ethyl 5-methyl-1-methyl-pyrazolecarboxylate (16.8 g, 100 mmol) was dissolved in 100 mL of dry. Tetrahydrofuran was slowly added dropwise to the three-necked flask, and stirring was continued for 4 hours after completion of the addition. After the reduction is completed, absolute ethanol is added dropwise to remove the remaining lithium tetrahydroaluminum, the tetrahydrofuran is removed under reduced pressure, 500 mL of methanol is added, the pH is adjusted to neutral, the mixture is heated to reflux for 6 hours, and the filtrate is filtrated. The filtrate is concentrated and dissolved in 100 mL of dichloromethane. And washed twice with 50 mL of saturated aqueous sodium chloride, and the organic layer was dried and concentrated to give 5-methyl-1-methyl-pyrazolemethanol 8.8 g, 70percent.5-methyl-1-carbonitrileThe base-pyrazole methanol (6.3 g, 50 mmol) was dissolved in 20 mL of methylene chloride. Thionyl chloride (6 g, 50 mmol) was slowly added dropwise. After the addition was complete, stirring was continued for 2 hours. After the reaction was complete, saturated sodium bicarbonate was added slowly. The aqueous solution was adjusted to pH neutral and then extracted with 200 mL of dichloromethane. The organic layers were combined, dried and concentrated to give 3-chloromethyl-1-methyl-5-methylpyrazole (6.5 g, 90percent).In a 50 mL round bottom flask was added 3-chloromethyl-1-methyl-5-methylpyrazole (1.44 g, 10 mmol) and N-(2,4,6-trimethylphenyl)imidazole (1.86 g) (10 mmol), 20 mL of acetonitrile, and the mixture was heated under reflux for 6 hours, cooled to room temperature, and the solvent was distilled off under reduced pressure. The obtained solid was dissolved in water and filtered. The filtrate was saturated with aqueous solution of ammonium hexafluorophosphate, and the solid precipitated and was dried to give 3.8. g imidazolium salt ligand (HL1PF6), yield 88percent.
Reference：
[1] Journal of Medicinal Chemistry, 2015, vol. 58, # 5, p. 2180 - 2194
[2] Anales de Quimica, 1996, vol. 92, # 2, p. 70 - 78
[3] Organic Letters, 2011, vol. 13, # 6, p. 1436 - 1439
[4] Patent: CN106478734, 2017, A, . Location in patent: Paragraph 0027; 0028; 0029
[5] Medicinal Chemistry Research, 2012, vol. 21, # 10, p. 2772 - 2778,7
[6] Patent: WO2018/178227, 2018, A1, . Location in patent: Page/Page column 31-32
With lithium aluminium tetrahydride; In tetrahydrofuran; for 4h;
Ethyl 5-methyl-1-hydro-pyrazolecarboxylate (30.8 g, 200 mmol) was dissolved in 200 mL of dry tetrahydrofuran solution. Sodium hydride (4.8 g, 200 mmol) was slowly added under ice-cooling and sodium hydride was added completely. After the temperature was raised to 50C, the mixture was stirred for 1 hour and cooled to room temperature. Methyl iodide (28.2 g, 200 mmol) was then dissolved in 100 mL of tetrahydrofuran and slowly added dropwise to the reaction. The addition was complete and heating to 50C was continued for 2 hours. After the reaction is complete, cool to room temperature, remove tetrahydrofuran under reduced pressure, then add 100 mL of water, extract with ethyl acetate (100 mL x 3), combine the organic layers, dry, and remove the ethyl acetate under reduced pressure to give 5-methyl-1-carbonitrile. Ethyl 2-pyrazolecarboxylate 26.6 g, 85%.Lithium aluminum hydride (3.8 g, 100 mmol) was added to a dry three-necked flask, 200 mL of dry tetrahydrofuran, and then ethyl 5-methyl-1-methyl-pyrazolecarboxylate (16.8 g, 100 mmol) was dissolved in 100 mL of dry. Tetrahydrofuran was slowly added dropwise to the three-necked flask, and stirring was continued for 4 hours after completion of the addition. After the reduction is completed, absolute ethanol is added dropwise to remove the remaining lithium tetrahydroaluminum, the tetrahydrofuran is removed under reduced pressure, 500 mL of methanol is added, the pH is adjusted to neutral, the mixture is heated to reflux for 6 hours, and the filtrate is filtrated. The filtrate is concentrated and dissolved in 100 mL of dichloromethane. And washed twice with 50 mL of saturated aqueous sodium chloride, and the organic layer was dried and concentrated to give 5-methyl-1-methyl-pyrazolemethanol 8.8 g, 70%.5-methyl-1-carbonitrileThe base-pyrazole methanol (6.3 g, 50 mmol) was dissolved in 20 mL of methylene chloride. Thionyl chloride (6 g, 50 mmol) was slowly added dropwise. After the addition was complete, stirring was continued for 2 hours. After the reaction was complete, saturated sodium bicarbonate was added slowly. The aqueous solution was adjusted to pH neutral and then extracted with 200 mL of dichloromethane. The organic layers were combined, dried and concentrated to give 3-chloromethyl-1-methyl-5-methylpyrazole (6.5 g, 90%).In a 50 mL round bottom flask was added 3-chloromethyl-1-methyl-5-methylpyrazole (1.44 g, 10 mmol) and N-(2,4,6-trimethylphenyl)imidazole (1.86 g) (10 mmol), 20 mL of acetonitrile, and the mixture was heated under reflux for 6 hours, cooled to room temperature, and the solvent was distilled off under reduced pressure. The obtained solid was dissolved in water and filtered. The filtrate was saturated with aqueous solution of ammonium hexafluorophosphate, and the solid precipitated and was dried to give 3.8. g imidazolium salt ligand (HL1PF6), yield 88%.
With lithium aluminium tetrahydride; In tetrahydrofuran; at 4 - 23℃; for 1.5h;Large scale;
LAH (1.05 M in THF, 15.0 kg, 17.4 mol) was gradually added to a stirring solution of <strong>[5744-51-4]ethyl 1,5-dimethyl-1H-pyrazole-3-carboxylate</strong> (5.33 kg, 31 .7 mol) in THF (10.7 L) over 1.5 h at 4- 23 C, followed by THF (1.0 L). After 30 min, the solution was cooled to 15 C, then, while continuing to cool, a solution of water (0.66 L, 37 mol) in THF (1.9 L) was gradually added over 20 min. Aq. NaOH (15 wt%, 0.66 L, 2.8 mol) was then added over a few min, followed by water (2.0 L). The resulting slurry was stirred for 20 min at 4-1 1 C then filtered under suction. The collected solids were washed four times with THF (10.7 L per wash) to give (1 ,5-dimethyl-1 H- pyrazol-3-yl)methanol as a solution in the collected filtrates. (0239
Preparation 1 Ethyl-1,5-dimethylpyrazole-3-carboxylate. STR14 Ethyl 2,4-dioxovalerate (5.6 ml, 40 mM) was dissolved in glacial acetic acid (35 ml) before cooling the reaction temperature to 8-10 C. Methylhydrazine (2.0 ml, 38 mM) was added dropwise so that the reaction temperature did not rise above 15 C. After stirring at room temperature for 90 minutes the reaction was poured into ethyl acetate and water. The organic phase was washed with saturated sodium bicarbonate solution, water and brine before drying (MgSO4). Purification was accomplished was by chromatography on silica gel (10*4.5 cm) loading in dichloromethane and eluding with 50% ethyl acetate in hexane. Evaporation of solvent gave the title compound as a coloured oil which crystallized on standing (4.69 g); numax (CH2 Cl2) 1717 and 1223 cm-1; deltaH (CDCl3) 1.39 (3H, t, J 7.13 Hz), 2.30 (3H, s), 3.85 (3H, s), 4.39 (2H, q, J 7.21 Hz), 6.57 (1H, s); E.I m/e 168 (25%).
6-(m-aminophenyl)-2,3,5,6-tetrahydroimidazo-[2,1-b[ No CAS ]
[ 81153-54-0 ]
Yield
Reaction Conditions
Operation in experiment
With hydrogenchloride;trimethylaluminum; In hexane; dichloromethane;
EXAMPLE 1 6-[m-(1,5-Dimethylpyrazole-3-carboxamido)phenyl]-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole To 6-(m-aminophenyl)-2,3,5,6-tetrahydroimidazo-[2,1-b[thiazole (2.2 g, 10 mmol) in dry dichloromethane (30 ml) under nitrogen at room temperature was added trimethylaluminium (6 ml; 25% in hexane). After 20 mins <strong>[5744-51-4]1,5-dimethylpyrazole-3-carboxylic acid ethyl ester</strong> (1.8 g; 11 mmol) in dry dichloromethane (2 ml) was added and the solution heated under reflux for 24 hours. Hydrochloric acid (20 ml; 2 N aqueous) was added slowly, the resulting solution basified with aqueous ammonia solution (100 ml; 5 N) and extracted with chloroform (3*200 ml). After drying (MgSO4) the combined organic phases were concentrated in vacuo to afford an oil which was separated on aluminia eluding with chloroform to afford the amide (2.9 g; 85%). Treatment of the amide with isopropanolic hydrogen chloride gave a white solid after removal of the solvent. Recrystallisation from ethanol afforded the hydrochloride (2 g). (Found: C: 53.17; H: 5.25; N: 18.15; Cl: 10.27. C17 H19 N5 OS.1.1HCl requires C: 53.53; H: 5.27; N: 18.36; Cl: 10.23%) m.pt. 168-170 C.
(1S,3S,7S,10R,11S,12S,16S)-3-((Z)-1-(1,5-dimethyl-1H-pyrazol-3-yl)prop-1-en-2-yl)-8,8,10,12,16-pentamethyl-7,11-bis(trimethylsilyloxy)-4-oxabicyclo[14.1.0]heptadecane-5,9-dione[ No CAS ]
Ethyl 5-methyl-1-hydro-pyrazolecarboxylate (30.8 g, 200 mmol) was dissolved in 200 mL of dry tetrahydrofuran solution. Sodium hydride (4.8 g, 200 mmol) was slowly added under ice-cooling and sodium hydride was added completely. After the temperature was raised to 50C, the mixture was stirred for 1 hour and cooled to room temperature. Methyl iodide (28.2 g, 200 mmol) was then dissolved in 100 mL of tetrahydrofuran and slowly added dropwise to the reaction. The addition was complete and heating to 50C was continued for 2 hours. After the reaction is complete, cool to room temperature, remove tetrahydrofuran under reduced pressure, then add 100 mL of water, extract with ethyl acetate (100 mL x 3), combine the organic layers, dry, and remove the ethyl acetate under reduced pressure to give 5-methyl-1-carbonitrile. Ethyl 2-pyrazolecarboxylate 26.6 g, 85%.Lithium aluminum hydride (3.8 g, 100 mmol) was added to a dry three-necked flask, 200 mL of dry tetrahydrofuran, and then ethyl 5-methyl-1-methyl-pyrazolecarboxylate (16.8 g, 100 mmol) was dissolved in 100 mL of dry. Tetrahydrofuran was slowly added dropwise to the three-necked flask, and stirring was continued for 4 hours after completion of the addition. After the reduction is completed, absolute ethanol is added dropwise to remove the remaining lithium tetrahydroaluminum, the tetrahydrofuran is removed under reduced pressure, 500 mL of methanol is added, the pH is adjusted to neutral, the mixture is heated to reflux for 6 hours, and the filtrate is filtrated. The filtrate is concentrated and dissolved in 100 mL of dichloromethane. And washed twice with 50 mL of saturated aqueous sodium chloride, and the organic layer was dried and concentrated to give 5-methyl-1-methyl-pyrazolemethanol 8.8 g, 70%.5-methyl-1-carbonitrileThe base-pyrazole methanol (6.3 g, 50 mmol) was dissolved in 20 mL of methylene chloride. Thionyl chloride (6 g, 50 mmol) was slowly added dropwise. After the addition was complete, stirring was continued for 2 hours. After the reaction was complete, saturated sodium bicarbonate was added slowly. The aqueous solution was adjusted to pH neutral and then extracted with 200 mL of dichloromethane. The organic layers were combined, dried and concentrated to give 3-chloromethyl-1-methyl-5-methylpyrazole (6.5 g, 90%).In a 50 mL round bottom flask was added 3-chloromethyl-1-methyl-5-methylpyrazole (1.44 g, 10 mmol) and N-(2,4,6-trimethylphenyl)imidazole (1.86 g) (10 mmol), 20 mL of acetonitrile, and the mixture was heated under reflux for 6 hours, cooled to room temperature, and the solvent was distilled off under reduced pressure. The obtained solid was dissolved in water and filtered. The filtrate was saturated with aqueous solution of ammonium hexafluorophosphate, and the solid precipitated and was dried to give 3.8. g imidazolium salt ligand (HL1PF6), yield 88%.
ethyl 7-(3-((4-(4-acetylpiperazin-1-yl)phenoxy)methyl)-1,5-dimethyl-1H-pyrazol-4-yl)-3-(3-(naphthalen-1-yloxy)propyl)-1-(pyridin-3-ylmethyl)-1H-indole-2-carboxylate[ No CAS ]
ethyl 7-(3-((4-(4-acetylpiperazin-1-yl)phenoxy)methyl)-1,5-dimethyl-1H-pyrazol-4-yl)-3-(3-(naphthalen-1-yloxy)propyl)-1H-indole-2-carboxylate[ No CAS ]
(Z)-1-(1,5-dimethyl-1H-pyrazol-3-yl)-3-hydroxybut-2-en-1-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
35%
General procedure: To a suspension of sodium (15.21 mmol) in 20 mL of toluene, the appropriate heterocyclic carboxylate (12.01 mmol) in 25 mL of toluene was slowly added; then acetone or aryl methyl ketones (12.01 mmol) in 10 mL of toluene was added at 0 C. The resulting mixture was stirred at room temperature for two days. The precipitate formed was filtered, washed with toluene, dissolved in water, and neutralized with acetic acid to pH 5. After extraction with CH2Cl2, the organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The obtained residue was filtered through silica using CH2Cl2/MeOH as eluant to give the desired products 1-10 as a white solid in 35%-48% yield. beta-keto-enol forms were recrystallized from methanol (95%) to obtain target compounds 1-10 which were confirmed by FT-IR, 1H-NMR, 13C-NMR, elemental analysis, and mass spectroscopy.
(Z)-1-(1,5-dimethyl-1H-pyrazol-3-yl)-3-hydroxy-3-phenylprop-2-en-1-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
32%
General procedure: To a suspension of sodium (15.21 mmol) in 20 mL of toluene, the appropriate heterocyclic carboxylate (12.01 mmol) in 25 mL of toluene was slowly added; then acetone or aryl methyl ketones (12.01 mmol) in 10 mL of toluene was added at 0 C. The resulting mixture was stirred at room temperature for two days. The precipitate formed was filtered, washed with toluene, dissolved in water, and neutralized with acetic acid to pH 5. After extraction with CH2Cl2, the organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The obtained residue was filtered through silica using CH2Cl2/MeOH as eluant to give the desired products 1-10 as a white solid in 35%-48% yield. beta-keto-enol forms were recrystallized from methanol (95%) to obtain target compounds 1-10 which were confirmed by FT-IR, 1H-NMR, 13C-NMR, elemental analysis, and mass spectroscopy.
(Z)-1-(1,5-dimethyl-1H-pyrazol-3-yl)-3-hydroxy-3-p-tolyprop-2-en-1-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
22%
General procedure: To a suspension of sodium (15.21 mmol) in 20 mL of toluene, the appropriate heterocyclic carboxylate (12.01 mmol) in 25 mL of toluene was slowly added; then acetone or aryl methyl ketones (12.01 mmol) in 10 mL of toluene was added at 0 C. The resulting mixture was stirred at room temperature for two days. The precipitate formed was filtered, washed with toluene, dissolved in water, and neutralized with acetic acid to pH 5. After extraction with CH2Cl2, the organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The obtained residue was filtered through silica using CH2Cl2/MeOH as eluant to give the desired products 1-10 as a white solid in 35%-48% yield. beta-keto-enol forms were recrystallized from methanol (95%) to obtain target compounds 1-10 which were confirmed by FT-IR, 1H-NMR, 13C-NMR, elemental analysis, and mass spectroscopy.
(Z)-1-(1,5-dimethyl-1H-pyrazol-3-yl)-3-hydroxy-3-(4-methoxyphenyl)prop-2-en-1-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
31%
General procedure: To a suspension of sodium (15.21 mmol) in 20 mL of toluene, the appropriate heterocyclic carboxylate (12.01 mmol) in 25 mL of toluene was slowly added; then acetone or aryl methyl ketones (12.01 mmol) in 10 mL of toluene was added at 0 C. The resulting mixture was stirred at room temperature for two days. The precipitate formed was filtered, washed with toluene, dissolved in water, and neutralized with acetic acid to pH 5. After extraction with CH2Cl2, the organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The obtained residue was filtered through silica using CH2Cl2/MeOH as eluant to give the desired products 1-10 as a white solid in 35%-48% yield. beta-keto-enol forms were recrystallized from methanol (95%) to obtain target compounds 1-10 which were confirmed by FT-IR, 1H-NMR, 13C-NMR, elemental analysis, and mass spectroscopy.
With N-Bromosuccinimide; In 1,2-dichloro-ethane; at 80℃; for 15h;
N-Bromosuccinimide (16.3 g, 90.5 mmol) was added to a solution of ethyl 1 ,5-dimethyl-1 H- pyrazole-3-carboxylate (7.25 g, 43.1 mmol, CAS No 5744-51-4) in 1 ,2-dichloroethane (150 ml) and the mixture was stirred for 15 h at 80C. For work-up, the mixture was diluted with dichloromethane, washed with water and the organic phase was filtrated through a silicone filter and concentrated. The residue was purified by flash chromatography (Biotage SNAP _ _ cartridge silica 340 g, hexanes/dichloromethane gradient, 0->100% dichloromethane) to give the title compound (6.49 g, 61 % yield). (2857) -NMR (400 MHz, DMSO-d6) delta [ppm]: 1.261 (4.14), 1.278 (8.78), 1.296 (4.21 ), 2.268 (14.94), 2.518 (0.74), 2.523 (0.49), 3.857 (16.00), 4.229 (1.31), 4.247 (4.03), 4.264 (3.94), 4.282 (1.24).
61%
With N-Bromosuccinimide; In 1,2-dichloro-ethane; at 80℃; for 15h;
N-Bromosuccinimide (16.3 g, 90.5 mmol) was added to a solution of ethyl 1 ,5-dimethyl-1 H- pyrazole-3-carboxylate (7.25 g, 43.1 mmol, CAS No 5744-51 -4) in 1 ,2-dichloroethane (150 mL) and the mixture was stirred for 15 h at 80. For w ork-up, the mixture was diluted with dichloromethane, washed with water and the organic phase was filtrated through a silicone filter and concentrated. The residue was purified by flash chromatography (Biotage SNAP cartridge silica 340 g, hexanes/dichloromethane gradient, 0->100% dichloromethane) to give the title compound (6.49 g, 61 % yield). 1 H-NMR (400 MHz, DMSO-d6) d [ppm]: 1 .261 (4.14), 1 .278 (8.78), 1 .296 (4.21 ), 2.268 (14.94), 2.518 (0.74), 2.523 (0.49), 3.857 (16.00), 4.229 (1 .31 ), 4.247 (4.03), 4.264 (3.94), 4.282 (1.24).
61%
With N-Bromosuccinimide; In 1,2-dichloro-ethane; at 80℃; for 15h;
N-Bromosuccinimide (16.3 g, 90.5 mmol) was added to a solution of ethyl 1 ,5-dimethyl-1 H- pyrazole-3-carboxylate (7.25 g, 43.1 mmol, CAS No 5744-51 -4 ) in 1 ,2-dichloroethane (150 mL) and the mixture was stirred for 15 h at dOTT F or work-up, the mixture was diluted with dichloromethane, washed with water and the organic phase was filtered through a silicone filter and concentrated. The residue was purified by flash chromatography (Biotage SNAP cartridge silica 340 g, 0->100% dichloromethane//hexane gradient) to give the title compound (6.49 g, 61 % yield). 1 H-NMR (400 MHz, DMSO-d6) d [ppm]: 1 .261 (4.14), 1 .278 (8.78), 1 .296 (4.21 ), 2.268 (14.94), 2.518 (0.74), 2.523 (0.49), 3.857 (16.00), 4.229 (1.31 ), 4.247 (4.03), 4.264 (3.94), 4.282 (1.24).
61%
With N-Bromosuccinimide; In 1,2-dichloro-ethane; at 80℃; for 15h;
N-Bromosuccinimide (16.3 g, 90.5 mmol) was added to a solution of ethyl 1,5-dimethyl-1H- pyrazole-3-carboxylate (7.25 g, 43.1 mmol, CAS No 5744-51 -4) in 1 ,2-dichloroethane (150 mL) and the mixture was stirred for 15 h at 80. For w ork-up, the mixture was diluted with dichloromethane, washed with water and the organic phase was filtered through a silicone filter and concentrated. The residue was purified by flash chromatography (Biotage SNAP cartridge silica 340 g, hexane/dichloromethane gradient, 0->100% dichloromethane) to give the title compound (6.49 g, 61 % yield).1H-NMR (400 MHz, DMSO-d6) d [ppm]: 1 .261 (4.14), 1 .278 (8.78), 1 .296 (4.21 ), 2.268 (14.94), 2.518 (0.74), 2.523 (0.49), 3.857 (16.00), 4.229 (1.31 ), 4.247 (4.03), 4.264 (3.94), 4.282 (1.24).
61%
With N-Bromosuccinimide; In 1,2-dichloro-ethane; at 80℃; for 15h;
N-Bromosuccinimide (16.3 g, 90.5 mmol) was added to a solution of ethyl 1,5-dimethyl-1H- pyrazole-3-carboxylate (7.25 g, 43.1 mmol, CAS No 5744-51 -4) in 1,2-dichloroethane (150 mL) and the mixture was stirred for 15 h at 80. For w ork-up, the mixture was diluted with dichloromethane, washed with water and the organic phase was filtrated through a silicone filter and concentrated. The residue was purified by flash chromatography (Biotage SNAP cartridge silica 340 g, hexanes/dichloromethane gradient, 0->100% dichloromethane) to give the title compound (6.49 g, 61 % yield). 1H-NMR (400 MHz, DMSO-d6) d [ppm]: 1.261 (4.14), 1.278 (8.78), 1.296 (4.21), 2.268 (14.94), 2.518 (0.74), 2.523 (0.49), 3.857 (16.00), 4.229 (1.31), 4.247 (4.03), 4.264 (3.94), 4.282 (1.24).
61%
With N-Bromosuccinimide; In 1,2-dichloro-ethane; at 80℃; for 15h;
N-Bromosuccinimide (16.3 g, 90.5 mmol) was added to a solution of ethyl 1,5-dimethyl-1H- pyrazole-3-carboxylate (7.25 g, 43.1 mmol, CAS No 5744-51 -4) in 1,2-dichloroethane (150 ml) and the mixture was stirred for 15 h at 80TT For work-up, the mixture was diluted with dichloromethane, washed with water and the organic phase was filtrated through a silicone filter and concentrated. The residue was purified by flash chromatography (Biotage SNAP cartridge silica 340 g, hexanes/dichloromethane gradient, 0->100% dichloromethane) to give the title compound (6.49 g, 61 % yield). 1H-NMR (400 MHz, DMSO-d6) d [ppm]: 1.261 (4.14), 1.278 (8.78), 1.296 (4.21), 2.268 (14.94), 2.518 (0.74), 2.523 (0.49), 3.857 (16.00), 4.229 (1.31), 4.247 (4.03), 4.264 (3.94), 4.282 (1.24).
6.49 g
With N-Bromosuccinimide; In 1,2-dichloro-ethane; at 80℃; for 15h;
N-Bromosuccinimide (16.3 g, 90.5 mmol, CAS 128-08-5) was added to a solution of ethyl 1 ,5- dimethyl-1 H-pyrazole-3-carboxylate (7.25 g, 43.1 mmol, CAS 5744-51 -4) in 1 ,2-dichloroethane (150 ml_), and the mixture was stirred for 15 hours at 80C. For work-up, the mixture was diluted with dichloromethane, washed with water and the organic phase was filtered through a water resistant filter and concentrated. The residue was purified by flash chromatography (Biotage SNAP cartridge silica 340 g, hexane/dichloromethane gradient, 0-100% dichloromethane) to give the title compound (6.49 g). LC-MS (Method 1 ): Rt = 0.97 min; MS (ESIpos): m/z = 247 [M+H]+ 1H-NMR (400 MHz, DMSO-d6) d [ppm]: 1 .261 (4.14), 1.278 (8.78), 1 .296 (4.21 ), 2.268 (14.94), 2.518 (0.74), 2.523 (0.49), 3.857 (16.00), 4.229 (1.31 ), 4.247 (4.03), 4.264 (3.94), 4.282 (1 .24).
ethyl 1-{3-[(tert-butoxycarbonyl)(methyl)amino]propyl}-7-[3-(hydroxymethyl)-1,5-dimethyl-1H-pyrazol-4-yl]-3-[3-(naphthalen-1-yloxy)propyl]-1H-indole-2-carboxylate[ No CAS ]
ethyl 7-[3-(bromomethyl)-1,5-dimethyl-1H-pyrazol-4-yl]-1-{3-[(tert-butoxycarbonyl)(methyl)amino]propyl}-3-[3-(naphthalen-1-yloxy)propyl]-1H-indole-2-carboxylate[ No CAS ]
ethyl 7-[3-(bromomethyl)-1,5-dimethyl-1H-pyrazol-4-yl]-1-[3-(methylamino)propyl]-3-[3-(naphthalen-1-yloxy)propyl]-1H-indole-2-carboxylate hydrochloric acid salt[ No CAS ]
(rac)-ethyl 7,10,11-trimethyl-1-[3-(naphthalen-1-yloxy)propyl]-4,5,6,7,8,10-hexahydropyrazolo[3',4':7,8][1,5]diazecino[9,10,1-hi]indole-2-carboxylate[ No CAS ]
ethyl 7-{1,5-dimethyl-3-[(prop-2-en-1-yloxy)methyl]-1H-pyrazol-4-yl}-3-[3-(naphthalen-1-yloxy)propyl]-1-(prop-2-en-1-yl)-1H-indole-2-carboxylate[ No CAS ]
(rac)-(E/Z)-ethyl 2,3-dimethyl-7-[3-(naphthalen-1-yloxy)propyl]-2,10,13,15-tetrahydropyrazolo[4',3':9,10][1,6]oxazacycloundecino[8,7,6-hi]indole-8-carboxylate[ No CAS ]
R(a)-7,10,11-trimethyl-1-[3-(naphthalen-1-yloxy)propyl]-4,5,6,7,8,10-hexahydropyrazolo[3',4':7,8][1,5]diazecino[9,10,1-hi]indole-2-carboxylic acid N-ethylethanamine salt[ No CAS ]
S(a)-7,10,11-trimethyl-1-[3-(naphthalen-1-yloxy)propyl]-4,5,6,7,8,10-hexahydropyrazolo[3',4':7,8][1,5]diazecino[9,10,1-hi]indole-2-carboxylic acid N-ethylethanamine salt[ No CAS ]
(R<SUB>a</SUB>)-methyl 6-chloro-7-(3-(hydroxymethyl)-1,5-dimethyl-1H-pyrazol-4-yl)-3-(3-methoxy-3-oxopropyl)-1-methyl-1H-indole-2-carboxylate[ No CAS ]
(R<SUB>a</SUB>)-3-(2-carboxyethyl)-6-chloro-7-(3-(((4-methoxybenzyl)oxy)methyl)-1,5-dimethyl-1H-pyrazol-4-yl)-1-methyl-1H-indole-2-carboxylic acid (1R)-1-(2-nitrophenyl)ethanamine (1 :1 salt)[ No CAS ]
ethyl 3-(3-((tert-butyldimethylsilyl)oxy)propyl)-6-chloro-7-(3-((cyclopropylamino)methyl)-1,5-dimethyl-1H-pyrazol-4-yl)-1H-indole-2-carboxylate[ No CAS ]
ethyl 3-(3-((tert-butyldimethylsilyl)oxy)propyl)-6-chloro-7-(3-((3-chloro-N-cyclopropylpropylsulfonamido)methyl)-1,5-dimethyl-1H-pyrazol-4-yl)-1H-indole-2-carboxylate[ No CAS ]
(rac)-ethyl 1-(3-((tert-butyldimethylsilyl)oxy)propyl)-13-chloro-8-cyclopropyl-11,12-dimethyl-5,6,9,11-tetrahydro-4H,8H-pyrazolo[3',4':4,5][1]thia[2,8]diazacycloundecino[6,7,8-hi]indole-2-carboxylate 7,7-dioxide[ No CAS ]
(rac)-ethyl 13-chloro-8-cyclopropyl-1-(3-hydroxypropyl)-11,12-dimethyl-5,6,9,11-tetrahydro-4H,8H-pyrazolo[3',4':4,5][1]thia[2,8]diazacycloundecino[6,7,8-hi]indole-2-carboxylate 7,7-dioxide[ No CAS ]
(rac)-ethyl 1-(3-bromopropyl)-13-chloro-8-cyclopropyl-11,12-dimethyl-5,6,9,11-tetrahydro-4H,8H-pyrazolo[3',4':4,5][1]thia[2,8]diazacycloundecino[6,7,8-hi]indole-2-carboxylate 7,7-dioxide[ No CAS ]
(rac)-ethyl 13-chloro-8-cyclopropyl-11,12-dimethyl-1-(3-(naphthalen-1-yloxy)propyl)-5,6,9,11-tetrahydro-4H,8H-pyrazolo[3',4':4,5][1]thia[2,8]diazacycloundecino[6,7,8-hi]indole-2-carboxylate 7,7-dioxide[ No CAS ]
(rac)-ethyl 13-chloro-8-cyclopropyl-1-(3-((6-fluoronaphthalen-1-yl)oxy)propyl)-11,12-dimethyl-5,6,9,11-tetrahydro-4H,8H-pyrazolo[3',4':4,5][1]thia[2,8]diazacycloundecino[6,7,8-hi]indole-2-carboxylate 7,7-dioxide[ No CAS ]
ethyl 6-chloro-7-(3-(((2,4-dimethoxybenzyl)amino)methyl)-1,5-dimethyl-1H-pyrazol-4-yl)-3-(3-((6-fluoronaphthalen-1-yl)oxy)propyl)-1H-indole-2-carboxylate[ No CAS ]
ethyl 6-chloro-7-(3-(((3-chloro-N-(2,4-dimethoxybenzyl)propyl)sulfonamido)methyl)-1,5-dimethyl-1H-pyrazol-4-yl)-3-(3-((6-fluoronaphthalen-1-yl)oxy)propyl)-1H-indole-2-carboxylate[ No CAS ]
(rac)-ethyl 13-chloro-8-(2,4-dimethoxybenzyl)-1-(3-((6-fluoronaphthalen-1-yl)oxy)propyl)-11,12-dimethyl-5,6,9,11-tetrahydro-4H,8H-pyrazolo[3',4':4,5][1]thia[2,8]diazacycloundecino[6,7,8-hi]indole-2-carboxylate 7,7-dioxide[ No CAS ]
(rac)-ethyl 13-chloro-1-(3-((6-fluoronaphthalen-1-yl)oxy)propyl)-11,12-dimethyl-5,6,9,11-tetrahydro-4H,8H-pyrazolo[3',4':4,5][1]thia[2,8]diazacycloundecino[6,7,8-hi]indole-2-carboxylate 7,7-dioxide[ No CAS ]
ethyl 6-chloro-7-(5-ethyl-3-((ethylamino)methyl)-1-methyl-1H-pyrazol-4-yl)-3-(3-((6-fluoronaphthalen-1-yl)oxy)propyl)-1H-indole-2-carboxylate[ No CAS ]
ethyl 6-chloro-7-(3-(((3-chloro-N-ethylpropyl)sulfonamido)methyl)-5-ethyl-1-methyl-1H-pyrazol-4-yl)-3-(3-((6-fluoronaphthalen-1-yl)oxy)propyl)-1H-indole-2-carboxylate[ No CAS ]
(rac)-ethyl 13-chloro-8,12-diethyl-1-(3-((6-fluoronaphthalen-1-yl)oxy)propyl)-11-methyl-5,6,9,11-tetrahydro-4H,8H-pyrazolo[3,4 :4,5][1]thia[2,8]diazacycloundecino[6,7,8-hi]indole-2-carboxylate 7,7-dioxide[ No CAS ]
ethyl 7-[3-({(3-chloropropane-1-sulfonyl)[2-(morpholin-4-yl)ethyl]amino}methyl)-1,5-dimethyl-1H-pyrazol-4-yl]-3-{3-[(naphthalen-1-yl)oxy]propyl}-1H-indole-2-carboxylate[ No CAS ]
ethyl 6-chloro-7-(5-ethyl-3-(((4-methoxybenzyl)amino)methyl)-1-methyl-1H-pyrazol-4-yl)-3-(3-((6-fluoronaphthalen-1-yl)oxy)propyl)-1H-indole-2-carboxylate[ No CAS ]
ethyl 6-chloro-7-(3-(((3-chloro-N-(4-methoxybenzyl)propyl)sulfonamido)methyl)-5-ethyl-1-methyl-1H-pyrazol-4-yl)-3-(3-((6-fluoronaphthalen-1-yl)oxy)propyl)-1H-indole-2-carboxylate[ No CAS ]
(rac)-methyl 13-chloro-12-ethyl-1-(3-((6-fluoronaphthalen-1-yl)oxy)propyl)-8-(4-methoxybenzyl)-11-methyl-5,6,9,11-tetrahydro-4H,8H-pyrazolo[3,4:4,5][1]thia[2,8]diazacycloundecino[6,7,8-hi]indole-2-carboxylate 7,7-dioxide[ No CAS ]
(rac)-methyl 13-chloro-12-ethyl-1-(3-((6-fluoronaphthalen-1-yl)oxy)propyl)-11-methyl-5,6,9,11-tetrahydro-4H,8H-pyrazolo[3,4:4,5][1]thia[2,8]diazacycloundecino[6,7,8-hi]indole-2-carboxylate 7,7-dioxide[ No CAS ]
(rac)-ethyl 2,3-dimethyl-14-[2-(morpholin-4-yl)ethyl]-7-{3-[(naphthalen-1-yl)oxy]propyl}-13,13-dioxo-10,11,12,13,14,15-hexahydro-2H-13λ6-pyrazolo[3',4':4,5][1,2,8]thiadiazacycloundecino-[6,7,8-hi]indole-8-carboxylate[ No CAS ]
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