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CAS No. :750586-06-2 MDL No. :MFCD22571479
Formula : C9H10BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :RQAHVOLDFUBDMB-UHFFFAOYSA-N
M.W : 244.09 Pubchem ID :59145915
Synonyms :

Safety of [ 750586-06-2 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 750586-06-2 ]

* 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 [ 750586-06-2 ]

[ 750586-06-2 ] Synthesis Path-Downstream   1~23

  • 1
  • [ 18583-89-6 ]
  • [ 750586-06-2 ]
YieldReaction ConditionsOperation in experiment
55% Reference Example 1; methyl 3-amino-6-bromo-2-methylbenzoate [Show Image]; To a mixed solution of <strong>[18583-89-6]methyl 3-amino-2-methylbenzoate</strong> (5.00 mL, 34.7 mmol) in acetic acid (100 mL) and methanol (200 mL) was added bromine (5.55 g, 34.7 mmol) under ice-cooling and the mixture was stirred for 5 min. The reaction solution was diluted with saturated aqueous sodium thiosulfate solution, and the organic solvent was evaporated under reduced pressure. The residual aqueous solution was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=5/95-->20/80) to give the title compound (4.66 g, yield 55percent). 1H-NMR (CDCl3) delta: 2.08 (3H, s), 3.70 (2H, brs), 3.94 (3H, s), 6.58 (1H, d, J = 8.5 Hz), 7.18 (1H, d, J = 8.5 Hz).
55% Reference Example 67 methyl 3-amino-6-bromo-2-methylbenzoate To a mixture of <strong>[18583-89-6]methyl 3-amino-2-methylbenzoate</strong> (5.00 mL, 34.7 mmol) in acetic acid (100 mL)-methanol (200 mL) was added bromine (5.55 g, 34.7 mmol) under ice-cooling, and the mixture was stirred for 5 min. The reaction solution was diluted with saturated aqueous sodium thiosulfate solution, and the organic solvent was evaporated under reduced pressure. The residual aqueous solution was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=5/95-->20/80) to give the title compound (4.66 g, yield 55percent). 1H-NMR (CDCl3) delta: 2.08 (3H, s), 3.70 (2H, br s), 3.94 (3H, s), 6.58 (1H, d, J = 8.5 Hz), 7.18 (1H, d, J = 8.5 Hz).
  • 2
  • [ 750586-06-2 ]
  • [ 1037840-79-1 ]
YieldReaction ConditionsOperation in experiment
86% Stage #1: methyl 3-amino-6-bromo-2-methylbenzoate With acetic acid; sodium nitrite In water at 10 - 35℃; Stage #2: With sodium hydrogencarbonate In water 2 Reference Example 2; methyl 5-bromo-1H-indazole-4-carboxylate [Show Image]; To a solution of methyl 3-amino-6-bromo-2-methylbenzoate (5.44 g, 22.3 mmol) in acetic acid (110 mL) was added a solution of sodium nitrite (1.69 g, 24.5 mmol) in water (11 mL) at room temperature and, after stirring for 20 hr, the organic solvent was evaporated under reduced pressure. The residual aqueous solution was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane=10/90→30/70) to give the title compound (4.86 g, yield 86%). 1H-NMR (CDCl3) δ: 4.06 (3H, s), 7.48 (1H, dd, J = 8.8, 1.1 Hz), 7.63 (1H, d, J = 8.8 Hz), 8.26 (1H, d, J = 1.1 Hz), 10.59 (1H, brs), melting point: 164 - 165°C (recrystallized from ethyl acetate), elemental analysis: for C9H7N2O2Br•0.1H2O Calculated (%): C, 42.08; H, 2.83; N, 10.91 Found (%): C, 41.97; H, 2.93; N, 10.97.
86% Stage #1: methyl 3-amino-6-bromo-2-methylbenzoate With acetic acid; sodium nitrite In water at 20℃; Stage #2: With sodium hydrogencarbonate In water 68 Reference Example 68 methyl 5-bromo-1H-indazole-4-carboxylate To a solution of methyl 3-amino-6-bromo-2-methylbenzoate (5.44 g, 22.3 mmol) in acetic acid (110 mL) was added a solution of sodium nitrite (1.69 g, 24.5 mmol) in water (11 mL) at room temperature, and the mixture was stirred for 20 hr. The organic solvent was evaporated under reduced pressure. The residual aqueous solution was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane=10/90→30/70) to give the title compound (4.86 g, yield 86%). 1H-NMR (CDCl3) δ: 4.06 (3H, s), 7.48 (1H, dd, J = 8.8, 1.1 Hz), 7.63 (1H, d, J = 8.8 Hz), 8.26 (1H, d, J = 1.1 Hz), 10.59 (1H, br s), melting point: 164 - 165°C (recrystallized from ethyl acetate), elemental analysis: for C9H7N2O2Br·0.1H2O Calculated (%): C, 42.08; H, 2.83; N, 10.91 Found (%): C, 41.97; H, 2.93; N, 10.97.
86% With sodium nitrite In water; acetic acid at 20℃; for 20h;
4.9 g With acetic acid; sodium nitrite In water at 10 - 35℃; for 3h; 1.B B) methyl 5-bromo-1H-indazole-4-carboxylate B) methyl 5-bromo-1H-indazole-4-carboxylate To a mixture of methyl 3-amino-6-bromo-2-methylbenzoate (7.2 g) and acetic acid (150 mL) was added a solution of sodium nitrite (2.2 g) in water (15 mL) at room temperature, and the mixture was stirred at room temperature for 3 hr and concentrated. The obtained residue was partitioned with an ethyl acetate-saturated aqueous sodium hydrogen carbonate solution, and the organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained solid was crystallized from ethyl acetate/hexane to give the title compound (4.9 g). 1H NMR (300 MHz, DMSO-d6) δ 3.98 (3H, s), 7.58-7.66 (1H, m), 7.67-7.73 (1H, m), 8.18 (1H, d, J = 0.9 Hz), 13.56 (1H, brs).

  • 3
  • [ 750586-06-2 ]
  • [ 1037841-33-0 ]
YieldReaction ConditionsOperation in experiment
96% With N-chloro-succinimide In acetonitrile at 60℃; for 15h; Cooling with ice; 55 Reference Example 55; methyl 3-amino-6-bromo-5-chloro-2-methylbenzoate [Show Image]; To a solution of methyl 3-amino-6-bromo-2-methylbenzoate (960 mg, 3.93 mmol) in acetonitrile (40 mL) was added N-chlorosuccinimide (525 mg, 3.93 mmol) under ice-cooling, and the mixture was stirred at 60°C for 15 hr. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=0/100→30/70) to give the title compound (1.05 g, yield 96%). 1H-NMR (CDCl3) δ: 2.13 (3H, s), 3.93 (3H, s), 4.13 (2H, brs), 7.36 (1H, s), MS (ESI+): 278 (M+H).
  • 4
  • [ 750586-06-2 ]
  • methyl 3,6-dibromo-2-methylbenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
97.5% With tert.-butylnitrite; copper(I) bromide In methanol; acetonitrile at 60 - 70℃; for 3h; 1.1; 2.1; 3.1 Synthesis of S1,3,6-dibromo-2-methylbenzoate: A 500 ml three-necked flask was charged with 23.2 g of copper bromide, 200 ml of methanol, and 13.4 g of tert-butyl nitrite, and heated to 60 ° C. 26.1 g of methyl 3-amino-6-bromo-2-methylbenzoate was added to 100 ml of acetonitrile, and the solution was added dropwise to the reaction system at 60-70 ° C, and the temperature was raised to 65 ° C for 3 hours. TLC analysis of the raw materials was complete. The reaction solution was poured into 500 ml of water and extracted with methyl tert-butyl ether (2 × 250 ml). The methyl tert-butyl ether was combined, concentrated and dried, and passed through column chromatography (PE: EA = 10 : 1) 32 g of methyl 3,6-dibromo-2-methylbenzoate was obtained in a yield of 97.5%.
  • 5
  • [ 750586-06-2 ]
  • (3,6-dibromo-2-methylphenyl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: copper(I) bromide; tert.-butylnitrite / acetonitrile; methanol / 3 h / 60 - 70 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 5 °C
  • 6
  • [ 750586-06-2 ]
  • 3,6-dibromo-2-methylbenzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: copper(I) bromide; tert.-butylnitrite / acetonitrile; methanol / 3 h / 60 - 70 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 5 °C 3: manganese(IV) oxide / dichloromethane / 12 h / Reflux
  • 7
  • [ 750586-06-2 ]
  • [ 1037840-80-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic acid; sodium nitrite / water / 3 h / 10 - 35 °C 2: ethyl acetate / 3 h / 10 - 35 °C
Multi-step reaction with 2 steps 1: sodium nitrite / water; acetic acid / 20 h / 20 °C 2: ethyl acetate / 2.5 h / 20 °C
  • 8
  • [ 750586-06-2 ]
  • methyl 2,5-dimethyl-2H-indazole-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: acetic acid; sodium nitrite / water / 3 h / 10 - 35 °C 2: ethyl acetate / 3 h / 10 - 35 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate tribasic heptahydrate / 1,2-dimethoxyethane / 5 h / Reflux; Inert atmosphere
  • 9
  • [ 750586-06-2 ]
  • (2,5-dimethyl-2H-indazol-4-yl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: acetic acid; sodium nitrite / water / 3 h / 10 - 35 °C 2: ethyl acetate / 3 h / 10 - 35 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate tribasic heptahydrate / 1,2-dimethoxyethane / 5 h / Reflux; Inert atmosphere 4: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere
  • 10
  • [ 750586-06-2 ]
  • 4-(azidomethyl)-2,5-dimethyl-2H-indazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: acetic acid; sodium nitrite / water / 3 h / 10 - 35 °C 2: ethyl acetate / 3 h / 10 - 35 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate tribasic heptahydrate / 1,2-dimethoxyethane / 5 h / Reflux; Inert atmosphere 4: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere 5: 1,8-diazabicyclo[5.4.0]undec-7-ene; diphenylphosphoranyl azide / N,N-dimethyl-formamide / 3 h / 10 - 35 °C
  • 11
  • [ 750586-06-2 ]
  • N-((2,5-dimethyl-2H-indazol-4-yl)methyl)-4-(trifluoromethoxy)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: acetic acid; sodium nitrite / water / 3 h / 10 - 35 °C 2: ethyl acetate / 3 h / 10 - 35 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate tribasic heptahydrate / 1,2-dimethoxyethane / 5 h / Reflux; Inert atmosphere 4: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere 5: 1,8-diazabicyclo[5.4.0]undec-7-ene; diphenylphosphoranyl azide / N,N-dimethyl-formamide / 3 h / 10 - 35 °C 6: palladium 10% on activated carbon; hydrogen / 3 h / 10 - 35 °C / 760.05 Torr 7: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide / 10 - 35 °C
  • 12
  • [ 750586-06-2 ]
  • 1-tert-butyl 4-methyl 5-bromo-1H-indazole-1,4-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic acid; sodium nitrite / water / 3 h / 10 - 35 °C 2: triethylamine; dmap / tetrahydrofuran / 3 h / 10 - 35 °C
  • 13
  • [ 750586-06-2 ]
  • 1-(2,5-dimethyl-2H-indazol-4-yl)methanamine hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: acetic acid; sodium nitrite / water / 3 h / 10 - 35 °C 2: ethyl acetate / 3 h / 10 - 35 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate tribasic heptahydrate / 1,2-dimethoxyethane / 5 h / Reflux; Inert atmosphere 4: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere 5: 1,8-diazabicyclo[5.4.0]undec-7-ene; diphenylphosphoranyl azide / N,N-dimethyl-formamide / 3 h / 10 - 35 °C 6: palladium 10% on activated carbon; hydrogen / 3 h / 10 - 35 °C / 760.05 Torr
  • 14
  • [ 750586-06-2 ]
  • methyl 6-bromo-3-chloro-2-methylbenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
68.8% With tert.-butylnitrite; copper dichloride In acetonitrile at 0 - 30℃; for 16h; Inert atmosphere; 2 Step 2: Methyl 6-bromo-3-chloro-2-methylbenzoate To a stirring solution of copper(II) chloride (2.53 g, 18.85 mmol) and tert-butyl nitrite (3.31 mL, 28.3 mmol) in acetonitrile (20 mL) was added a solution of methyl 3-amino-6- bromo-2-methylbenzoate (2.3 g, 9.42 mmol) in acetonitrile (20 mL) dropwise under N2 at 0 °C. The resulting reaction mixture was slowly warmed to 30 °C and stirred for 16 hr at the same temperature. The reaction was quenched with water (50 mL) and extracted with EtOAc (2 x 25 mL). The combined organic extracts were washed with water (25 mL) and brine (25 mL), dried over Na2SO4 and concentrated in vacuo. The brown liquid residue was purified by column chromatography (Biotage, 25 g SNAP column, 0-10% EtOAc/ pet ether over 40 min) to give the title compound as an orange liquid (1.75 g, 6.49 mmol, 68.8% yield). GCMS (m/z) 264.0 (M+H)+.
  • 15
  • [ 750586-06-2 ]
  • [ 1037841-46-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: sodium nitrite / water; acetic acid / 20 h / 20 °C 2.1: ethyl acetate / 2.5 h / 20 °C 3.1: potassium carbonate; palladium diacetate; triphenylphosphine / N,N-dimethyl-formamide / 0.83 h / 100 °C 4.1: hydrogen; palladium 10% on activated carbon / methanol; water / 12 h / 20 °C 5.1: methanol; sodium hydride / tetrahydrofuran; mineral oil / 3 h / Reflux 5.2: 4 h / 100 °C 6.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 20 °C 6.2: 0.5 h / 50 °C 7.1: ammonia; hydrogen / ethanol / 3 h / 20 °C 8.1: triethylamine / tetrahydrofuran / 0.25 h / 0 °C 9.1: hydrogen; palladium 10% on activated carbon / methanol; water / 3 h / 20 °C
  • 16
  • [ 750586-06-2 ]
  • [ 1037841-51-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: sodium nitrite / water; acetic acid / 20 h / 20 °C 2.1: ethyl acetate / 2.5 h / 20 °C 3.1: potassium carbonate; palladium diacetate; triphenylphosphine / N,N-dimethyl-formamide / 0.83 h / 100 °C 4.1: hydrogen; palladium 10% on activated carbon / methanol; water / 12 h / 20 °C 5.1: methanol; sodium hydride / tetrahydrofuran; mineral oil / 3 h / Reflux 5.2: 4 h / 100 °C 6.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 20 °C 6.2: 0.5 h / 50 °C 7.1: ammonia; hydrogen / ethanol / 3 h / 20 °C 8.1: triethylamine / tetrahydrofuran / 0.25 h / 0 °C 9.1: hydrogen; palladium 10% on activated carbon / methanol; water / 3 h / 20 °C
  • 17
  • [ 750586-06-2 ]
  • methyl 5-[3-methoxy-3-oxoprop-1-en-1-yl]-2-methyl-2H-indazole-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium nitrite / water; acetic acid / 20 h / 20 °C 2: ethyl acetate / 2.5 h / 20 °C 3: potassium carbonate; palladium diacetate; triphenylphosphine / N,N-dimethyl-formamide / 0.83 h / 100 °C
  • 18
  • [ 750586-06-2 ]
  • [ 1037840-84-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium nitrite / water; acetic acid / 20 h / 20 °C 2: ethyl acetate / 2.5 h / 20 °C 3: potassium carbonate; palladium diacetate; triphenylphosphine / N,N-dimethyl-formamide / 0.83 h / 100 °C 4: hydrogen; palladium 10% on activated carbon / methanol; water / 12 h / 20 °C
  • 19
  • [ 750586-06-2 ]
  • [ 1037840-94-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium nitrite / water; acetic acid / 20 h / 20 °C 2.1: ethyl acetate / 2.5 h / 20 °C 3.1: potassium carbonate; palladium diacetate; triphenylphosphine / N,N-dimethyl-formamide / 0.83 h / 100 °C 4.1: hydrogen; palladium 10% on activated carbon / methanol; water / 12 h / 20 °C 5.1: methanol; sodium hydride / tetrahydrofuran; mineral oil / 3 h / Reflux 5.2: 4 h / 100 °C
  • 20
  • [ 750586-06-2 ]
  • (E)-2-(2-methyl-6,7-dihydrocyclopenta[e]indazol-8(2H)-ylidene)acetonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sodium nitrite / water; acetic acid / 20 h / 20 °C 2.1: ethyl acetate / 2.5 h / 20 °C 3.1: potassium carbonate; palladium diacetate; triphenylphosphine / N,N-dimethyl-formamide / 0.83 h / 100 °C 4.1: hydrogen; palladium 10% on activated carbon / methanol; water / 12 h / 20 °C 5.1: methanol; sodium hydride / tetrahydrofuran; mineral oil / 3 h / Reflux 5.2: 4 h / 100 °C 6.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 20 °C 6.2: 0.5 h / 50 °C
  • 21
  • [ 750586-06-2 ]
  • (E)-2-(2-methyl-6,7-dihydrocyclopenta[e]indazol-8(2H)-ylidene)ethanamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: sodium nitrite / water; acetic acid / 20 h / 20 °C 2.1: ethyl acetate / 2.5 h / 20 °C 3.1: potassium carbonate; palladium diacetate; triphenylphosphine / N,N-dimethyl-formamide / 0.83 h / 100 °C 4.1: hydrogen; palladium 10% on activated carbon / methanol; water / 12 h / 20 °C 5.1: methanol; sodium hydride / tetrahydrofuran; mineral oil / 3 h / Reflux 5.2: 4 h / 100 °C 6.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 20 °C 6.2: 0.5 h / 50 °C 7.1: ammonia; hydrogen / ethanol / 3 h / 20 °C
  • 22
  • [ 750586-06-2 ]
  • (E)-N-[2-(2-methyl-6,7-dihydrocyclopenta[e]indazol-8(2H)-ylidene)ethyl]acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: sodium nitrite / water; acetic acid / 20 h / 20 °C 2.1: ethyl acetate / 2.5 h / 20 °C 3.1: potassium carbonate; palladium diacetate; triphenylphosphine / N,N-dimethyl-formamide / 0.83 h / 100 °C 4.1: hydrogen; palladium 10% on activated carbon / methanol; water / 12 h / 20 °C 5.1: methanol; sodium hydride / tetrahydrofuran; mineral oil / 3 h / Reflux 5.2: 4 h / 100 °C 6.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 20 °C 6.2: 0.5 h / 50 °C 7.1: ammonia; hydrogen / ethanol / 3 h / 20 °C 8.1: triethylamine / tetrahydrofuran / 0.25 h / 0 °C
  • 23
  • [ 750586-06-2 ]
  • (E)-N-[2-(2-methyl-6,7-dihydrocyclopenta[e]indazol-8(2H)-ylidene)ethyl]propionamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: sodium nitrite / water; acetic acid / 20 h / 20 °C 2.1: ethyl acetate / 2.5 h / 20 °C 3.1: potassium carbonate; palladium diacetate; triphenylphosphine / N,N-dimethyl-formamide / 0.83 h / 100 °C 4.1: hydrogen; palladium 10% on activated carbon / methanol; water / 12 h / 20 °C 5.1: methanol; sodium hydride / tetrahydrofuran; mineral oil / 3 h / Reflux 5.2: 4 h / 100 °C 6.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 20 °C 6.2: 0.5 h / 50 °C 7.1: ammonia; hydrogen / ethanol / 3 h / 20 °C 8.1: triethylamine / tetrahydrofuran / 0.25 h / 0 °C
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