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CAS No. :35826-59-6 MDL No. :MFCD00084855
Formula : C11H14O3 Boiling Point : -
Linear Structure Formula :- InChI Key :ROEMZKPINYTSKV-UHFFFAOYSA-N
M.W : 194.23 Pubchem ID :3015807
Synonyms :

Safety of [ 35826-59-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H227-H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 35826-59-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 35826-59-6 ]

[ 35826-59-6 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 35826-59-6 ]
  • [ 13205-46-4 ]
YieldReaction ConditionsOperation in experiment
90% With iodine; aluminium In acetonitrile at 20℃; for 18h;
With alkali
  • 3
  • [ 99-76-3 ]
  • [ 75-26-3 ]
  • [ 35826-59-6 ]
YieldReaction ConditionsOperation in experiment
100% With potassium carbonate In acetone for 72h; Inert atmosphere; Reflux; Methyl 4-isopropoxybenzoate (10) A well-stirred solution of methyl 4-hydroxybenzoate (22.82 g, 150 mmol) in acetone (340 mL) was treated with potassium carbonate (72.56 g, 525 mmol, 3.5 equiv.) and 2-bromopropane (21.10 mL, 225 mmol, 1.5 equiv.) and refluxed for 72 hours. The mixture was filtered, the precipitate washed with several portions of acetone, and the combined filtrate and washings evaporated under reduced pressure. The oil was partitioned between saturated aqueous sodium hydrogen carbonate (150 mL) and chloroform (150 mL). The layers were separated and the aqueous layer was extracted with chloroform (2 × 75 mL). The combined organic phases were washed with saturated aqueous sodium hydrogen carbonate (2 × 100 mL), brine (100 mL), dried (MgSO4), the solvent evaporated under reduced pressure, and dried under high vaccum with stirring to give pure 10 as a colorless oil (29.14 g, 100%). Rf 0.32 (petroleum spirit 40-60 °C-EtOAc, 90:10); 1H NMR (400 MHz, CDCl3) δ 7.96 (2H, d, J = 9.2 Hz, ArH), 6.88 (2H, d, J = 9.2 Hz, ArH), 4.63 (1H, sep, J = 6.0 Hz, OCH), 3.87 (3H, s, OCH3), 1.35 (6H, d, J = 6.0 Hz, CHCH3); 13C NMR (100 MHz, CDCl3) δ 167.1 (C=O), 162.0 (CAr), 131.7 (2C, CArH), 122.3 (CAr), 115.2 (2C, CArH), 70.2 (OCH), 51.9 (OCH3), 22.0 (2C, CHCH3).
100% With potassium carbonate In acetone for 72h; Inert atmosphere; Reflux;
94.7% With potassium carbonate In acetone at 85℃; for 72h; Sealed tube; 1.1.1; 2.2.1 The DPPEF precursor synthesis reaction is as follows: Step 1-1, add methylparaben (9.615 g, 63.2 mmol,) to a 350 mL pressure bottle.1.0 eq), anhydrous potassium carbonate (30.570 g, 221 mmol, 3.5 eq),150 mL of acetone and 2-bromopropane (11.660 g, 94.8 mmol, 1.5 eq), sealed at 85 °C for 72 h,the reaction system is concentrated, column chromatography separation (PE: EA = 20:1) gave a colorless transparent liquid 11.627g (Substance 1), yield 94.7%.
80% With sodium hydride In N,N-dimethyl-formamide at 60℃;

  • 4
  • [ 35826-59-6 ]
  • 5-(4-isopropoxy-phenyl)-4-(4-methoxy-phenyl)-2,3-dihydro-1<i>H</i>-pyrazol-3-ylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 81 percent / NaH / tetrahydrofuran / 60 °C 2: 84 percent / hydrazine dihydrochloride / aq. ethanol / Heating
  • 5
  • [ 35826-59-6 ]
  • 2-(4-hydroxyphenyl)-3-(4-methoxyphenyl)-5,7-bis(trifluoromethyl)pyrazolo[1,5-a]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 81 percent / NaH / tetrahydrofuran / 60 °C 2: 84 percent / hydrazine dihydrochloride / aq. ethanol / Heating 3: 75 percent / AcOH / Heating 4: 83 percent / AlCl3 / CH2Cl2 / 12 h / 20 °C
  • 6
  • [ 35826-59-6 ]
  • 2-(4-isopropoxy-phenyl)-3-(4-methoxy-phenyl)-5,7-bis-trifluoromethyl-1,3a-dihydro-pyrazolo[1,5-<i>a</i>]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 81 percent / NaH / tetrahydrofuran / 60 °C 2: 84 percent / hydrazine dihydrochloride / aq. ethanol / Heating 3: 75 percent / AcOH / Heating
  • 7
  • [ 35826-59-6 ]
  • 4-{2-[4-(2-dimethylamino-ethoxy)-phenyl]-5,7-bis-trifluoromethyl-pyrazolo[1,5-<i>a</i>]pyrimidin-3-yl}-phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 81 percent / NaH / tetrahydrofuran / 60 °C 2: 84 percent / hydrazine dihydrochloride / aq. ethanol / Heating 3: 75 percent / AcOH / Heating 4: 83 percent / AlCl3 / CH2Cl2 / 12 h / 20 °C 5: 65 percent / triphenylphosphine; diisopropyl diazodicarboxylate / tetrahydrofuran / 48 h / 20 °C 6: 74 percent / AlCl3; EtSH / CH2Cl2
  • 8
  • [ 35826-59-6 ]
  • [ 924907-87-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 81 percent / NaH / tetrahydrofuran / 60 °C 2: 84 percent / hydrazine dihydrochloride / aq. ethanol / Heating 3: 75 percent / AcOH / Heating 4: 83 percent / AlCl3 / CH2Cl2 / 12 h / 20 °C 5: 65 percent / triphenylphosphine; diisopropyl diazodicarboxylate / tetrahydrofuran / 48 h / 20 °C
  • 9
  • [ 35826-59-6 ]
  • [ 924907-86-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 81 percent / NaH / tetrahydrofuran / 60 °C 2: 84 percent / hydrazine dihydrochloride / aq. ethanol / Heating 3: 75 percent / AcOH / Heating 4: 83 percent / AlCl3 / CH2Cl2 / 12 h / 20 °C 5: 70 percent / triphenylphosphine; diisopropyl diazodicarboxylate / tetrahydrofuran / 48 h / 20 °C
  • 10
  • [ 35826-59-6 ]
  • 4-{2-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5,7-bis-trifluoromethyl-pyrazolo[1,5-<i>a</i>]pyrimidin-3-yl}-phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 81 percent / NaH / tetrahydrofuran / 60 °C 2: 84 percent / hydrazine dihydrochloride / aq. ethanol / Heating 3: 75 percent / AcOH / Heating 4: 83 percent / AlCl3 / CH2Cl2 / 12 h / 20 °C 5: 70 percent / triphenylphosphine; diisopropyl diazodicarboxylate / tetrahydrofuran / 48 h / 20 °C 6: 75 percent / AlCl3; EtSH / CH2Cl2
  • 11
  • [ 35826-59-6 ]
  • [ 75-05-8 ]
  • [ 884504-22-7 ]
YieldReaction ConditionsOperation in experiment
80.5% Stage #1: methyl 4-isopropoxybenzoate With sodium hydride In toluene at 0 - 80℃; for 0.166667h; Stage #2: acetonitrile In toluene at 85℃; 1.1.2; 2.2.2 Step 1-2, adding 1 [Compound 1] (11.627 g, 59.86 mmol, 1.0 eq) and 60 mL of toluene to a 250 mL three-necked flask. The ice salt was reduced to below 0 ° C and 60% sodium hydride (4.789 g, 119.72 mmol, was added in portions). 2.0eq), After heating to 80 ° C for 10 min, a solution of acetonitrile (12.287 g, 299.68 mmol, 5.0 eq) in toluene was added dropwise. Adding heat to the reaction at 85 °C for 16 ~ 18h, Cool down and cool, add 100 mL of n-hexane and stir. Reaction liquid filtration After draining, the filter cake is dissolved in 500 mL of ice water. Then, it was extracted with ethyl acetate (250 mL*2), and dried, concentrated, and then purified by column chromatography (PE: EA = 10:1) to give 9.791 g of white solid (subst. 2).
67% Stage #1: methyl 4-isopropoxybenzoate With sodium hydride In toluene; mineral oil at 0 - 80℃; Inert atmosphere; Stage #2: acetonitrile In toluene; mineral oil at 80℃; for 18h; Inert atmosphere; 3-(4-Isopropoxyphenyl)-3-oxopropanenitrile (11) A cooled (0 °C), well-stirred solution of 10 (37.69 g, 194 mmol) in toluene (210 mL) was treated portionwise with sodium hydride (60% dispersion in mineral oil, 15.52 g, 388 mmol, 2.0 equiv.). The mixture was heated to 80 °C for 10 minutes, and treated dropwise with a solution of acetonitrile (50.60 mL, 970 mmol, 5.0 equiv.) in toluene (50 mL). The mixture was stirred at 80 °C for 18 h during which time a thick precipitate formed. The mixture was cooled to ambient temperature and the precipitate filtered and washed with several portions of petroleum spirit (40-60 °C). The precipitate was dissolved in water (200 mL) with warming, cooled to 0 °C, and the sodium enolate precipitated by scratching. The precipitate was filtered, washed carefully with several portions of ice water, redissolved in water (200 mL) with warming, and allowed to cool to ambient temperature. The stirred solution was acidified to pH 2-3 using 1 M aqueous hydrochloric acid and the precipitate filtered and dried to give 11 as an off-white crystalline powder. Recrystallization from isopropanol-petroleum spirit (40-60 °C) gave fine white needles of analytical purity (26.35 g, 67%). m.p. 64-65 °C; Rf 0.74 (petroleum spirit 40-60 °C-EtOAc, 50:50); 1H NMR (400 MHz, CDCl3) δ 7.88 (2H, d, J = 8.8 Hz, ArH), 6.94 (2H, d, J = 8.8 Hz, ArH), 4.67 (1H, sep, J = 6.1 Hz, OCH), 4.00 (2H, s, CH2CN), 1.38 (6H, d, J = 6.1 Hz, CHCH3); 13C NMR (100 MHz, CDCl3) δ 185.4 (C=O), 163.48 (CAr), 131.1 (2C, CArH), 126.9 (CAr), 115.7 (2C, CArH), 114.2 (C≡N), 70.7 (OCH), 29.1 (CH2), 22.0 (2C, CHCH3); LRMS (+ESI) m/z 204.53 ([M + H]+, 100%); Anal. (C12H13NO2): calcd, C 70.92, H 6.45, N 6.89; found, C 70.97, H 6.71, N 6.84.
67% With sodium hydride In toluene at 80℃; for 18h; Inert atmosphere;
With sodium hydride In toluene at 80℃; for 18h; 28.b b) 3-(4-Isopropoxy-phenyl)-3-oxo-propionitrileTo a solution of 4-Isopropoxy-benzoic acid methyl ester (2.2 g, 11.2 mmol, 1.0 eq) in dry toluene (15 mL) under N2, NaH (50-60% dispersion in mineral oil, 1.1 g, 22.4 mmol, 2.0 eq) was added. The mixture was heated at 8O0C and then dry CH3CN was added dropwise (2.8 mL, 56.0 mmol, 5.0 eq). The reaction was heated for 18 hours, then was allowed to cool down to room temperature and acidified with HCl 2N. The organic phase was recovered and 2.0 g of crude were obtained and it was used for cyclization without further purification.C11H14O3

  • 12
  • [ 67-56-1 ]
  • [ 13205-46-4 ]
  • [ 35826-59-6 ]
YieldReaction ConditionsOperation in experiment
67% for 48h; Heating / reflux; 28.a a) 4-Isopropoxy-benzoic acid methyl ester3.0 g of 4-isopropoxy-benzoic acid (16.7 mmol, 1.0 eq) were dissolved in MeOH (20 mL) and a catalytic quantity of sulfuric acid was added; the mixture was heated at reflux for 2 days. The solvent was then evaporated and the residue was dissolved in DCM and washed with 10% NaOH. The organic phases were dried and evaporated to give 2.2 g of title product (yield 67%).C11H14O31H-NMR (dmso-d6): 1.25 (6H, d, J=6.4 Hz); 3.77 (3H5 s); 4.67-4.70 (IH, m); 6.96-6.98 (2H, m); 7.84-7.87 (2H, m).
With thionyl chloride at 0℃; for 1h; Reflux;
  • 13
  • [ 35826-59-6 ]
  • C11H20O3 [ No CAS ]
  • C11H20O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With Rh/Al2O3; hydrogen In methanol at 20℃; optical yield given as %de;
  • 14
  • [ 35826-59-6 ]
  • [ 1224582-23-3 ]
YieldReaction ConditionsOperation in experiment
Stage #1: methyl 4-isopropoxybenzoate With Rh/Al2O3; hydrogen In methanol at 20℃; Stage #2: With methanol; sodium methylate at 50℃;
  • 15
  • [ 35826-59-6 ]
  • [ 868072-17-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydride / toluene; mineral oil / 0 - 80 °C / Inert atmosphere 1.2: 18 h / 80 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere 2.3: 13 h / Inert atmosphere; Reflux 3.1: ethanol / 20 h / Reflux; Inert atmosphere 4.1: aluminum (III) chloride / dichloromethane / 0 - 20 °C / Inert atmosphere 4.2: 0 - 20 °C / Inert atmosphere
Multi-step reaction with 5 steps 1: sodium hydride / toluene / 18 h / 80 °C / Inert atmosphere 2: sodium hydride / tetrahydrofuran / 27 h / 0 - 20 °C / Inert atmosphere 3: hydrazine hydrate; acetic acid / ethanol / 13 h / Inert atmosphere; Reflux 4: ethanol / 20 h / Inert atmosphere; Reflux 5: aluminum (III) chloride / dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere
Multi-step reaction with 5 steps 1.1: sodium hydride / toluene / 0.17 h / 0 - 80 °C 1.2: 85 °C 2.1: sodium iodide; sodium hydroxide / ethanol / 20 - 25 °C 3.1: hydrazine hydrate; acetic acid / ethanol / 4 h / 100 °C 4.1: ethanol / 90 °C 5.1: aluminum (III) chloride / dichloromethane / 2 h / 30 °C
  • 16
  • [ 35826-59-6 ]
  • PBR099 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium hydride / toluene; mineral oil / 0 - 80 °C / Inert atmosphere 1.2: 18 h / 80 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere 2.3: 13 h / Inert atmosphere; Reflux 3.1: ethanol / 20 h / Reflux; Inert atmosphere 4.1: aluminum (III) chloride / dichloromethane / 0 - 20 °C / Inert atmosphere 4.2: 0 - 20 °C / Inert atmosphere 5.1: potassium carbonate / N,N-dimethyl-formamide / 40 °C / Inert atmosphere
  • 17
  • [ 35826-59-6 ]
  • [ 1254174-27-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium hydride / toluene; mineral oil / 0 - 80 °C / Inert atmosphere 1.2: 18 h / 80 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere 2.3: 13 h / Inert atmosphere; Reflux 3.1: ethanol / 20 h / Reflux; Inert atmosphere 4.1: aluminum (III) chloride / dichloromethane / 0 - 20 °C / Inert atmosphere 4.2: 0 - 20 °C / Inert atmosphere 5.1: potassium carbonate / N,N-dimethyl-formamide; toluene / 40 °C / Inert atmosphere
  • 18
  • [ 35826-59-6 ]
  • [ 1384517-64-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / toluene; mineral oil / 0 - 80 °C / Inert atmosphere 1.2: 18 h / 80 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: sodium hydride / toluene / 18 h / 80 °C / Inert atmosphere 2: sodium hydride / tetrahydrofuran / 27 h / 0 - 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: sodium hydride / toluene / 0.17 h / 0 - 80 °C 1.2: 85 °C 2.1: sodium iodide; sodium hydroxide / ethanol / 20 - 25 °C
  • 19
  • [ 35826-59-6 ]
  • [ 1384517-66-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / toluene; mineral oil / 0 - 80 °C / Inert atmosphere 1.2: 18 h / 80 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere 2.3: 13 h / Inert atmosphere; Reflux 3.1: ethanol / 20 h / Reflux; Inert atmosphere
Multi-step reaction with 4 steps 1: sodium hydride / toluene / 18 h / 80 °C / Inert atmosphere 2: sodium hydride / tetrahydrofuran / 27 h / 0 - 20 °C / Inert atmosphere 3: hydrazine hydrate; acetic acid / ethanol / 13 h / Inert atmosphere; Reflux 4: ethanol / 20 h / Inert atmosphere; Reflux
Multi-step reaction with 4 steps 1.1: sodium hydride / toluene / 0.17 h / 0 - 80 °C 1.2: 85 °C 2.1: sodium iodide; sodium hydroxide / ethanol / 20 - 25 °C 3.1: hydrazine hydrate; acetic acid / ethanol / 4 h / 100 °C 4.1: ethanol / 90 °C
  • 20
  • [ 35826-59-6 ]
  • 2-(2-(4-(benzyl)oxyphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-N,N-diethylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: sodium hydride / toluene / 18 h / 80 °C / Inert atmosphere 2: sodium hydride / tetrahydrofuran / 27 h / 0 - 20 °C / Inert atmosphere 3: hydrazine hydrate; acetic acid / ethanol / 13 h / Inert atmosphere; Reflux 4: ethanol / 20 h / Inert atmosphere; Reflux 5: aluminum (III) chloride / dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere 6: potassium carbonate / N,N-dimethyl-formamide / 14 h / 40 °C / Inert atmosphere
  • 21
  • [ 35826-59-6 ]
  • 2-(2-(4-isobutoxyphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-N,N-diethylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: sodium hydride / toluene / 18 h / 80 °C / Inert atmosphere 2: sodium hydride / tetrahydrofuran / 27 h / 0 - 20 °C / Inert atmosphere 3: hydrazine hydrate; acetic acid / ethanol / 13 h / Inert atmosphere; Reflux 4: ethanol / 20 h / Inert atmosphere; Reflux 5: aluminum (III) chloride / dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere 6: potassium carbonate / N,N-dimethyl-formamide / 14 h / 40 °C / Inert atmosphere
  • 22
  • [ 35826-59-6 ]
  • [ 1262278-66-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: sodium hydride / toluene / 18 h / 80 °C / Inert atmosphere 2: sodium hydride / tetrahydrofuran / 27 h / 0 - 20 °C / Inert atmosphere 3: hydrazine hydrate; acetic acid / ethanol / 13 h / Inert atmosphere; Reflux 4: ethanol / 20 h / Inert atmosphere; Reflux 5: aluminum (III) chloride / dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere 6: potassium carbonate / N,N-dimethyl-formamide / 120 h / 40 °C / Inert atmosphere
  • 23
  • [ 35826-59-6 ]
  • 2-(2-(4-cyclopentyloxyphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-N,N-diethylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: sodium hydride / toluene / 18 h / 80 °C / Inert atmosphere 2: sodium hydride / tetrahydrofuran / 27 h / 0 - 20 °C / Inert atmosphere 3: hydrazine hydrate; acetic acid / ethanol / 13 h / Inert atmosphere; Reflux 4: ethanol / 20 h / Inert atmosphere; Reflux 5: aluminum (III) chloride / dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere 6: potassium carbonate / N,N-dimethyl-formamide / 120 h / 45 °C / Inert atmosphere
  • 24
  • [ 35826-59-6 ]
  • 2-(2-(4-cyclopropylmethoxyphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-N,N-diethylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: sodium hydride / toluene / 18 h / 80 °C / Inert atmosphere 2: sodium hydride / tetrahydrofuran / 27 h / 0 - 20 °C / Inert atmosphere 3: hydrazine hydrate; acetic acid / ethanol / 13 h / Inert atmosphere; Reflux 4: ethanol / 20 h / Inert atmosphere; Reflux 5: aluminum (III) chloride / dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere 6: potassium carbonate / N,N-dimethyl-formamide / 20 h / 40 °C / Inert atmosphere
  • 25
  • [ 35826-59-6 ]
  • 2-(2-(4-cyclobutylmethoxyphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-N,N-diethylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: sodium hydride / toluene / 18 h / 80 °C / Inert atmosphere 2: sodium hydride / tetrahydrofuran / 27 h / 0 - 20 °C / Inert atmosphere 3: hydrazine hydrate; acetic acid / ethanol / 13 h / Inert atmosphere; Reflux 4: ethanol / 20 h / Inert atmosphere; Reflux 5: aluminum (III) chloride / dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere 6: potassium carbonate / N,N-dimethyl-formamide / 14 h / 40 °C / Inert atmosphere
  • 26
  • [ 35826-59-6 ]
  • 2-(2-(4-cyclopentylmethoxyphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-N,N-diethylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: sodium hydride / toluene / 18 h / 80 °C / Inert atmosphere 2: sodium hydride / tetrahydrofuran / 27 h / 0 - 20 °C / Inert atmosphere 3: hydrazine hydrate; acetic acid / ethanol / 13 h / Inert atmosphere; Reflux 4: ethanol / 20 h / Inert atmosphere; Reflux 5: aluminum (III) chloride / dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere 6: potassium carbonate / N,N-dimethyl-formamide / 120 h / 50 °C / Inert atmosphere
  • 27
  • [ 35826-59-6 ]
  • 2-(2-(4-cyclohexylmethoxyphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-N,N-diethylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: sodium hydride / toluene / 18 h / 80 °C / Inert atmosphere 2: sodium hydride / tetrahydrofuran / 27 h / 0 - 20 °C / Inert atmosphere 3: hydrazine hydrate; acetic acid / ethanol / 13 h / Inert atmosphere; Reflux 4: ethanol / 20 h / Inert atmosphere; Reflux 5: aluminum (III) chloride / dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere 6: potassium carbonate / N,N-dimethyl-formamide / 14 h / 40 °C / Inert atmosphere
  • 28
  • [ 35826-59-6 ]
  • 2-(2-(4-((2-fluorobenzyl)oxy)phenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-N,N-diethylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: sodium hydride / toluene / 18 h / 80 °C / Inert atmosphere 2: sodium hydride / tetrahydrofuran / 27 h / 0 - 20 °C / Inert atmosphere 3: hydrazine hydrate; acetic acid / ethanol / 13 h / Inert atmosphere; Reflux 4: ethanol / 20 h / Inert atmosphere; Reflux 5: aluminum (III) chloride / dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere 6: potassium carbonate / N,N-dimethyl-formamide / 14 h / 40 °C / Inert atmosphere
  • 29
  • [ 35826-59-6 ]
  • 2-(2-(4-((3-fluorobenzyl)oxy)phenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-N,N-diethylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: sodium hydride / toluene / 18 h / 80 °C / Inert atmosphere 2: sodium hydride / tetrahydrofuran / 27 h / 0 - 20 °C / Inert atmosphere 3: hydrazine hydrate; acetic acid / ethanol / 13 h / Inert atmosphere; Reflux 4: ethanol / 20 h / Inert atmosphere; Reflux 5: aluminum (III) chloride / dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere 6: potassium carbonate / N,N-dimethyl-formamide / 14 h / 40 °C / Inert atmosphere
  • 30
  • [ 35826-59-6 ]
  • 2-(2-(4-((4-fluorobenzyl)oxy)phenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-N,N-diethylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: sodium hydride / toluene / 18 h / 80 °C / Inert atmosphere 2: sodium hydride / tetrahydrofuran / 27 h / 0 - 20 °C / Inert atmosphere 3: hydrazine hydrate; acetic acid / ethanol / 13 h / Inert atmosphere; Reflux 4: ethanol / 20 h / Inert atmosphere; Reflux 5: aluminum (III) chloride / dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere 6: potassium carbonate / N,N-dimethyl-formamide / 14 h / 40 °C / Inert atmosphere
  • 31
  • [ 35826-59-6 ]
  • 2-(2-(4-((2-(trifluoromethyl)benzyl)oxy)phenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-N,N-diethylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: sodium hydride / toluene / 18 h / 80 °C / Inert atmosphere 2: sodium hydride / tetrahydrofuran / 27 h / 0 - 20 °C / Inert atmosphere 3: hydrazine hydrate; acetic acid / ethanol / 13 h / Inert atmosphere; Reflux 4: ethanol / 20 h / Inert atmosphere; Reflux 5: aluminum (III) chloride / dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere 6: potassium carbonate / N,N-dimethyl-formamide / 14 h / 40 °C / Inert atmosphere
  • 32
  • [ 35826-59-6 ]
  • 2-(2-(4-((3-(trifluoromethyl)benzyl)oxy)phenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-N,N-diethylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: sodium hydride / toluene / 18 h / 80 °C / Inert atmosphere 2: sodium hydride / tetrahydrofuran / 27 h / 0 - 20 °C / Inert atmosphere 3: hydrazine hydrate; acetic acid / ethanol / 13 h / Inert atmosphere; Reflux 4: ethanol / 20 h / Inert atmosphere; Reflux 5: aluminum (III) chloride / dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere 6: potassium carbonate / N,N-dimethyl-formamide / 14 h / 40 °C / Inert atmosphere
  • 33
  • [ 35826-59-6 ]
  • 2-(2-(4-((4-(trifluoromethyl)benzyl)oxy)phenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-N,N-diethylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: sodium hydride / toluene / 18 h / 80 °C / Inert atmosphere 2: sodium hydride / tetrahydrofuran / 27 h / 0 - 20 °C / Inert atmosphere 3: hydrazine hydrate; acetic acid / ethanol / 13 h / Inert atmosphere; Reflux 4: ethanol / 20 h / Inert atmosphere; Reflux 5: aluminum (III) chloride / dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere 6: potassium carbonate / N,N-dimethyl-formamide / 14 h / 40 °C / Inert atmosphere
  • 34
  • [ 35826-59-6 ]
  • 2-(2-(4-phenethoxyphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-N,N-diethylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: sodium hydride / toluene / 18 h / 80 °C / Inert atmosphere 2: sodium hydride / tetrahydrofuran / 27 h / 0 - 20 °C / Inert atmosphere 3: hydrazine hydrate; acetic acid / ethanol / 13 h / Inert atmosphere; Reflux 4: ethanol / 20 h / Inert atmosphere; Reflux 5: aluminum (III) chloride / dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere 6: potassium carbonate / N,N-dimethyl-formamide / 14 h / 40 °C / Inert atmosphere
  • 35
  • [ 35826-59-6 ]
  • [ 1384517-65-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium hydride / toluene / 18 h / 80 °C / Inert atmosphere 2: sodium hydride / tetrahydrofuran / 27 h / 0 - 20 °C / Inert atmosphere 3: hydrazine hydrate; acetic acid / ethanol / 13 h / Inert atmosphere; Reflux
Multi-step reaction with 3 steps 1.1: sodium hydride / toluene / 0.17 h / 0 - 80 °C 1.2: 85 °C 2.1: sodium iodide; sodium hydroxide / ethanol / 20 - 25 °C 3.1: hydrazine hydrate; acetic acid / ethanol / 4 h / 100 °C
  • 36
  • [ 35826-59-6 ]
  • 3-benzamido-4-isopropoxybenzohydroxamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: nitric acid; sulfuric acid / 0.5 h / 0 - 50 °C 2: hydrogenchloride; iron / methanol; water / 1 h / Reflux 3: N-ethyl-N,N-diisopropylamine / tetrahydrofuran 4: sodium hydroxide; water / methanol / 2 h / 50 °C 5: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C 6: hydrogenchloride / tetrahydrofuran; water / 20 °C
  • 37
  • [ 35826-59-6 ]
  • C22H26N2O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: nitric acid; sulfuric acid / 0.5 h / 0 - 50 °C 2: hydrogenchloride; iron / methanol; water / 1 h / Reflux 3: N-ethyl-N,N-diisopropylamine / tetrahydrofuran 4: sodium hydroxide; water / methanol / 2 h / 50 °C 5: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C
  • 39
  • [ 35826-59-6 ]
  • C11H15NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: nitric acid; sulfuric acid / 0.5 h / 0 - 50 °C 2: hydrogenchloride; iron / methanol; water / 1 h / Reflux
  • 40
  • [ 35826-59-6 ]
  • C18H19NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: nitric acid; sulfuric acid / 0.5 h / 0 - 50 °C 2: hydrogenchloride; iron / methanol; water / 1 h / Reflux 3: N-ethyl-N,N-diisopropylamine / tetrahydrofuran
  • 41
  • [ 35826-59-6 ]
  • C17H17NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: nitric acid; sulfuric acid / 0.5 h / 0 - 50 °C 2: hydrogenchloride; iron / methanol; water / 1 h / Reflux 3: N-ethyl-N,N-diisopropylamine / tetrahydrofuran 4: sodium hydroxide; water / methanol / 2 h / 50 °C
  • 42
  • [ 4885-02-3 ]
  • [ 35826-59-6 ]
  • [ 190271-78-4 ]
YieldReaction ConditionsOperation in experiment
82.8% With titanium tetrachloride In dichloromethane for 4h; Cooling with ice; 1.1 Under the ice salt bath,To a 100 ml round bottom flask, methyl p-isopropoxybenzoate (9.7 g, 50.0 mmol) was dissolved in dry dichloromethane (50 mL).Add 1,1-dichloromethyl ether (6.9 g, 60.0 mmol),TiCl4 (23.75 g, 125.0 mmol) was slowly added dropwise, and the mixture was stirred at this temperature for 4 hours.After the reaction was completed, the reaction was completed, and ice water was slowly added dropwise to the reaction flask to quench it, and the liquid phase was extracted three times with ethyl acetate. The organic phases were combined, dried, and the solvent was removed to obtain a yellow thick. The liquid was 9.2 g, and the yield was 82.8%.
  • 43
  • [ 35826-59-6 ]
  • [ 213598-11-9 ]
  • 44
  • [ 619-42-1 ]
  • [ 67-63-0 ]
  • [ 35826-59-6 ]
YieldReaction ConditionsOperation in experiment
84% With nickel(II) bromide trihydrate; N-isopropyl-N-tert-butylamine; 4,4'-di-tert-butyl-2,2'-bipyridine In acetonitrile at 40℃; for 120h; Irradiation; Sealed tube;
75% With (4,4′-di-tert-butyl-2,2′-dipyridyl)Ni(o-tolyl)(Br); 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 80℃; for 12h; Inert atmosphere; Sealed tube; UV-irradiation;
  • 45
  • [ 99-76-3 ]
  • [ 67-63-0 ]
  • [ 35826-59-6 ]
YieldReaction ConditionsOperation in experiment
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Inert atmosphere; 5.2.2. Synthesis of methyl alkoxy benzoate (B) General procedure: To a solution of methyl hydroxy benzoate (1 eq) in dry THF wereadded alcohol (1 eq) and triphenylphosphine (PPh3) (1.2 eq). The reactionmixture was allowed to stir at 0 °C (ice bath) for 15 min.Diisopropyl azodicarboxylate (DIAD) (1.2 eq) was added dropwise intothe cold solution and then stirred at room temperature for overnightunder N2. The mixture was diluted with water and extracted with ethylacetate twice, and the combined organic phase was washed with brinesolution, dried with Na2SO4, filtrated, and concentrated under reducedpressure. The residue was purified on a silica gel column.
  • 46
  • [ 579-74-8 ]
  • [ 35826-59-6 ]
  • 1-(4-isopropoxyphenyl)-3-(2-methoxyphenyl)propane-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
66.1% With sodium hydride In tetrahydrofuran; mineral oil Reflux; 5.2.4. Synthesis of 1,3-diketone derivatives (D) General procedure: To a suspension of sodium hydride (60% in mineral oil, 5 eq) in dryTHF was added solution of substituted methyl benzoate (2 eq) in dryTHF. After mixture refluxed, substituted acetophenone (1 eq) in dryTHF was added dropwise. The mixture was refluxed overnight, then quenched with 1 N HCl. The mixture was extracted with ethyl acetatetwice, and the combined organic phase was washed with brine solution,dried with anhydrous Na2SO4, filtrated, and concentrated under reduced pressure. The residue was purified on a silica gel column.
  • 47
  • [ 2040-04-2 ]
  • [ 35826-59-6 ]
  • 1-(2,6-dimethoxyphenyl)-3-(4-isopropoxyphenyl)propane-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
23.7% With sodium hydride In tetrahydrofuran; mineral oil Reflux; 5.2.4. Synthesis of 1,3-diketone derivatives (D) General procedure: To a suspension of sodium hydride (60% in mineral oil, 5 eq) in dryTHF was added solution of substituted methyl benzoate (2 eq) in dryTHF. After mixture refluxed, substituted acetophenone (1 eq) in dryTHF was added dropwise. The mixture was refluxed overnight, then quenched with 1 N HCl. The mixture was extracted with ethyl acetatetwice, and the combined organic phase was washed with brine solution,dried with anhydrous Na2SO4, filtrated, and concentrated under reduced pressure. The residue was purified on a silica gel column.
  • 48
  • [ 90-24-4 ]
  • [ 35826-59-6 ]
  • 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-isopropoxyphenyl)propane-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
55.6% With sodium hydride In tetrahydrofuran; mineral oil Reflux; 5.2.4. Synthesis of 1,3-diketone derivatives (D) General procedure: To a suspension of sodium hydride (60% in mineral oil, 5 eq) in dryTHF was added solution of substituted methyl benzoate (2 eq) in dryTHF. After mixture refluxed, substituted acetophenone (1 eq) in dryTHF was added dropwise. The mixture was refluxed overnight, then quenched with 1 N HCl. The mixture was extracted with ethyl acetatetwice, and the combined organic phase was washed with brine solution,dried with anhydrous Na2SO4, filtrated, and concentrated under reduced pressure. The residue was purified on a silica gel column.
  • 49
  • [ 2142-67-8 ]
  • [ 35826-59-6 ]
  • 1-(2-ethoxyphenyl)-3-(4-isopropoxyphenyl)propane-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
10% With sodium hydride In tetrahydrofuran; mineral oil Reflux; 5.2.4. Synthesis of 1,3-diketone derivatives (D) General procedure: To a suspension of sodium hydride (60% in mineral oil, 5 eq) in dryTHF was added solution of substituted methyl benzoate (2 eq) in dryTHF. After mixture refluxed, substituted acetophenone (1 eq) in dryTHF was added dropwise. The mixture was refluxed overnight, then quenched with 1 N HCl. The mixture was extracted with ethyl acetatetwice, and the combined organic phase was washed with brine solution,dried with anhydrous Na2SO4, filtrated, and concentrated under reduced pressure. The residue was purified on a silica gel column.
  • 50
  • [ 67-56-1 ]
  • [ 558-13-4 ]
  • [ 2741-16-4 ]
  • [ 35826-59-6 ]
YieldReaction ConditionsOperation in experiment
65% With Ni(PPh<SUB>3</SUB>)<SUB>2</SUB>Cl<SUB>2</SUB>; Bathocuproine at 120℃; for 24h; Inert atmosphere; Sealed tube; regioselective reaction;
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