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[ CAS No. 554411-20-0 ]

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Chemical Structure| 554411-20-0
Chemical Structure| 554411-20-0
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Product Details of [ 554411-20-0 ]

CAS No. :554411-20-0 MDL No. :MFCD06795663
Formula : C13H18BNO5 Boiling Point : 393.7°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :279.10 g/mol Pubchem ID :-
Synonyms :

Safety of [ 554411-20-0 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P321-P363-P405-P501 UN#:3261
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 554411-20-0 ]

  • Downstream synthetic route of [ 554411-20-0 ]

[ 554411-20-0 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 554411-20-0 ]
  • [ 188975-30-6 ]
  • [ 554411-21-1 ]
YieldReaction ConditionsOperation in experiment
66% With sodium carbonate In ethanol; water; toluene at 85℃; for 0.75h; 45 EXAMPLE 45; 2-(1H-Imidazol-2-yl)-4-methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazole 2.0 g Trifluoro-methanesulfonic acid 3,6-dihydro-2H-pyran-4-yl ester (8.6 mmol) and 2.89 g 2-(4-methoxy-3-nitro-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (10.3 mmol) were dissolved in a mixture of toluene (20 ml) and ethanol (50 ml) 0.35 g of dichloro (1,1'bis-(diphenylphosphine)ferrocene)palladium(II)dichloromethane (0.43 mmol) was added and heated to 85° C. Then aqueous sodium carbonate (2M) (10 ml) was added and the reaction kept at 85° C. for 45 min. After cooling to ambient temperature the reaction was extracted with ethyl acetate/water, the organic phase was dried over sodium sulfate and concentrated. Column chromatography on silica gel (n-heptane/ethyl acetate 4:1) yielded 1.33 g of 4-(4-methoxy-3-nitro-phenyl)-3,6-dihydro-2H-pyran (66%) as a yellow solid; M.p.: 117-120° C.
60% With sodium carbonate In ethanol; water; toluene at 80℃; for 0.333333h; 14. b b) 4-(4-Methoxy-3-nitro-phenyl)-3,6-dihydro-2H-pyran (VIII) To a stirred solution of 4.36 g (15.6 mmol) 2-(4-methoxy-3-nitro-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (VII) and 3.30 g (14.2 mmol) trifluoromethanesulfonic acid 3,6-dihydro-2H-pyran-4-yl ester in 33 ml ethanol and 82 ml toluene was added 580 mg (0.71 mmol) dichloro(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloromethane adduct. The mixture was heated at 80o C. and 16.5 ml (33.0 mmol) 2 M aqueous sodium carbonate solution was added dropwise. The reaction mixture was stirred for 20 minutes at 80o C. and then cooled to room temperature, poured onto water, and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (1 ethyl acetate/hexane) afforded 2.00 g (60%) 4-(4-methoxy-3-nitro-phenyl)-3,6-dihydro-2H-pyran (VIII) as a light yellow solid. ES-MS m/e (%): 253 (M+NH4+, 100), 236 (M+H+, 24).
60% With sodium carbonate In ethanol; water at 20 - 80℃; for 0.333333h;
  • 2
  • [ 33696-00-3 ]
  • [ 73183-34-3 ]
  • [ 554411-20-0 ]
YieldReaction ConditionsOperation in experiment
With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; at 80℃; for 2h; To a stirred solution of 1.30 g (5.60 mmol) <strong>[33696-00-3]4-bromo-2-nitroanisole</strong> (VI) in 25 ml DMSO were added 1.57 g (6.16 mmol) bis(pinacolato)diboron, 123 mg (0.17 mmol) dichloro(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloromethane adduct and 1.65 g (16.8 mmol) potassium acetate. The mixture was heated at 80o C. for 2 h and then cooled to room temperature, poured onto water, and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (1 ethyl acetate/hexane then ethyl acetate) afforded 1.39 g 2-(4-methoxy-3-nitro-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (VII) as an off-white solid. ES-MS m/e (%): 280 (M+H+, 100).
With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In dimethyl sulfoxide; at 80℃; for 2h; a 2-(4-Methoxy-3-nitro-phenyl)-4,4,5,5-tetramethyl-1,3,21 dioxaborolane To a stirred solution of 1.30 g (5.60 mmol) <strong>[33696-00-3]4-bromo-2-nitroanisole</strong> in 25 ml DMSO were added 1.57 g (6.16 mmol) bis(pinacolato)diboron, 123 mg (0.17 mmol) dichloro(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloromethane adduct and 1.65 g (16.8 mmol) potassium acetate. The mixture was heated at 80 C. for 2 h and then cooled to room temperature, poured onto water, and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (1/2 ethyl acetate/hexane then ethyl acetate) afforded 1.39 g 2-(4-methoxy-3-nitro-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane as an off-white solid. ES-MS m/e (%): 280 (M+H+, 100).
YieldReaction ConditionsOperation in experiment
83% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 90℃; Inert atmosphere; 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (97) General procedure: General procedure A: Potassium acetate (2.94 g, 30.0 mmol), bis-(pinacolato)-diboron (3.05 g, 12.0 mmol) and bis(diphenylphosphine) ferrocene dichloropalladium (II) complex with (0355) dichloromethane (0.36 g, 0.5 mmol) was added to an anhydrous solution of 4-bromo-2-methylphenol (1.87 g, 10.0 mmol) in dioxane (180 mL) under anhydrous conditions in an atmosphere of nitrogen. The mixture was stirred at 90 °C overnight. The reaction was then quenched with water and extracted with ethyl acetate The combined organic layers were dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash column chromatography on silica gel (eluent: dichloromethane/ethyl acetate, 10-100%) to give the title compound (12) as a white solid (1.75 g, 75%). ESI-MS m/z: 235.1508 [M+H]+; 1H NMR (400 MHz, CDC13) δ 7.60 (s, 1H), 7.55 (d, J= 7.9 Hz, 1H), 6.76 (d, J= 7.9 Hz, 1H), 4.97 (s, 1H), 2.25 (s, 3H), 1.33 (s, 12H); 13C NMR (101 MHz, CDC13) δ 156.77, 138.04, 134.46, 123.20, 114.56, 83.71, 24.99, 15.56.
80% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 110℃; for 12h; Inert atmosphere; 17.1 3) Synthesis of Intermediate 5-5 General procedure: Under nitrogen atmosphere, (20.1g, 60mmol) compound 5-4, (12.7g, 50mmol) pinacol diborate, (9.8g, 100mmol) potassium acetate, (2.2 g, 3mmol) Pd(ppf)Cl2and 100mL of 1,4-dioxane as a solvent were added to a 250mL three-necked flask, heated at 110 for 12 hours, when the reaction was completed, the reaction solution was cooled to room temperature, The filtrate was suction filtered, most of the solvent was removed by rotary evaporation, and the solution was washed with dichloromethane for 3 times. The organic solution was collected and mixed with silica gel for purification to obtain Intermediate 5-5 with a yield of 80%.
3.a a a 2-(4-Methoxy-3-nitro-phenyl)-4,4,5,5-tetramethyl-[1,3,2] dioxaborolane To a stirred solution of 1.30 g (5.60 mmol) 4-bromo-2-nitroanisole in 25 ml DMSO were added 1.57 g (6.16 mmol) bis(pinacolato)diboron, 123 mg (0.17 mmol) dichloro(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloromethane adduct and 1.65 g (16.8 mmol) potassium acetate. The mixture was heated at 80° C. for 2 h and then cooled to room temperature, poured onto water, and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (1/2 ethyl acetate/hexane then ethyl acetate) afforded 1.39 g 2-(4-methoxy-3-nitro-phenyl)-4,4,5,5-tetramethyl-[1,3,2] dioxaborolane as an off-white solid. ES-MS m/e (%): 280 (M+H+, 100).
  • 4
  • [ 18368-63-3 ]
  • [ 554411-20-0 ]
  • 2-(4-methoxy-3-nitrophenyl)-6-methylpyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.38 g With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,2-dimethoxyethane; water at 80℃; for 6.5h; 27 Reference Production Example 27 Reference Production Example 27 (1348) A mixture of 0.46 g of 2-chloro-6-methylpyridine, 1.00 g of a 4-methoxy-3-nitro-phenylboronic acid pinacol ester, 0.29 g of [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct, 1.52 g of tripotassium phosphate, 40 mL of 1,2-dimethoxyethane, and 5 mL of water was stirred at 80° C. for 6.5 hours. After cooling, water was added and the reaction mixture was filtered, and then the filtrate was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 0.38 g of 2-(4-methoxy-3-nitrophenyl)-6-methylpyridine (referred to as CA27). (1349) 1H-NMR (CDCl3) δ: 2.62 (3H, s), 4.01 (3H, s), 7.12 (1H, d, J=7.8 Hz), 7.17 (1H, d, J=8.8 Hz), 7.50 (1H, d, J=7.8 Hz), 7.66 (1H, t, J=7.8 Hz), 8.21 (1H, dd, J=8.8, 2.3 Hz), 8.52 (1H, d, J=2.3 Hz).
  • 5
  • [ 554411-20-0 ]
  • 2-(3-amino-4-methoxyphenyl)-6-methylpyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,2-dimethoxyethane / 6.5 h / 80 °C 2: acetic acid; iron / water / 9 h / 80 °C
  • 6
  • [ 554411-20-0 ]
  • 4-(6-methylpyridin-2-yl)-2-bromoanisole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,2-dimethoxyethane / 6.5 h / 80 °C 2: acetic acid; iron / water / 9 h / 80 °C 3: sodium nitrite; hydrogen bromide; copper(I) bromide / water / 3 h / 0 - 60 °C
  • 7
  • [ 554411-20-0 ]
  • [ 66346-85-8 ]
  • 3-(4-methoxy-3-nitrophenyl)-6-(pyrrolidin-1-yl)pyridazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
1 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; ethanol; water at 100℃; for 16h; 13.2 Step 2 Potassium carbonate (2.47 g, 0.179 mmol) was added to a stirred solution of compound 3-(4-methoxy-3-nitrophenyl-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (2.5 g, 0.089 mmol) and compound 3-chloro-6-(pyrrolidin-l-yl)pyridazine (1.6 g, 0.089 mmol) in 1,4 dioxane-ethanol -water (21 mL, 1 : 1 :0.1 v/v/v). The reaction mixture was purged with argon for 10 min and added Pd(PPh3)4 (0.310 g, 0.0027 mmol). The mixture was purged again with argon for 10 min. The reaction mixture was heated to 100°C for 16 h. After consumption of starting materials (monitored by TLC), reaction mixture was cooled to room temperature and filtered through celite bed. The solvent was concentrated under reduced pressure to get crude compound which was purified by flash chromatography (silica gel 230-400 mesh; 4-6% methanol in DCM) to get compound 3-(4-methoxy-3- nitrophenyl)-6-(pyrrolidin-l-yl)pyridazine as a pale yellow solid. Yield: (1.0 g, 41%). ES-MS [M+H]+:301; Rt = 1.46 min (Method-B). NMR (400 MHz, DMSO-de): d 8.49 (s, 1H), 8.33-8.30 (m, 1H), 7.99-7.96 (d, J =9.2 Hz, 1H), 7.62-7.54 (m, 3H), 7.448-7.46 (d, J=9.2Hz, 1H), 6.97-6.94 (m, 1H), 3.98 (s, 3H), 3.52-3.49 (m, 4H), 2.01-1.97 (m, 4H).
  • 8
  • [ 554411-20-0 ]
  • 2-methoxy-5-{6-(pyrrolidin-1-yl)pyridazin-3-yl}aniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / ethanol; water; 1,4-dioxane / 16 h / 100 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 16 h
  • 9
  • [ 554411-20-0 ]
  • N-(2-methoxy-5-(6-(pyrrolidin-1-yl)pyridazin-3-yl)phenyl)pentanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / ethanol; water; 1,4-dioxane / 16 h / 100 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 16 h 3: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 16 h / 0 - 20 °C
  • 10
  • [ 554411-20-0 ]
  • N-(2-hydroxy-5-(6-(pyrrolidin-1-yl)pyridazin-3-yl)phenyl)pentanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / ethanol; water; 1,4-dioxane / 16 h / 100 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 16 h 3: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 16 h / 0 - 20 °C 4: boron tribromide / dichloromethane / 2 h / 0 - 20 °C
  • 11
  • [ 554411-20-0 ]
  • [ 3842-55-5 ]
  • C22H16N4O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; sodium hydroxide In water; toluene at 80℃; for 12h; Inert atmosphere; 17.2 4) Synthesis of compound (2) General procedure: Under nitrogen atmosphere, (13.2g, 30mmol) of compound 2-4 and (8.6g, 30mmol) of compound 2-5, (1.72g, 1.5mmol) tetrakis(triphenyl) Phosphorus) palladium, (1.95g, 6mmol) tetrabutylammonium bromide, (2.4g, 60mmol) sodium hydroxide, (15mL) water and (90mL) toluene were added to a 250mL three-necked flask, heated at 80°C and stirred for 12 hours After finishing the reaction, the reaction solution was rotated to evaporate most of the solvent, and washed with dichloromethane dissolved in water 3 times, and the organic solution was collected and mixed with silica gel to pass through the column for purification to obtain compound (2) with a yield of 80%.
  • 12
  • [ 554411-20-0 ]
  • C21H14N4O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; sodium hydroxide / water; toluene / 12 h / 80 °C / Inert atmosphere 2: boron tribromide / dichloromethane / 13 h / 20 °C / Reflux
  • 13
  • [ 554411-20-0 ]
  • C22H13F3N4O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; sodium hydroxide / water; toluene / 12 h / 80 °C / Inert atmosphere 2: boron tribromide / dichloromethane / 13 h / 20 °C / Reflux 3: dmap / dichloromethane / 12 h / 20 °C
  • 14
  • [ 554411-20-0 ]
  • C37H23N4O2P [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; sodium hydroxide / water; toluene / 12 h / 80 °C / Inert atmosphere 2.1: boron tribromide / dichloromethane / 13 h / 20 °C / Reflux 3.1: dmap / dichloromethane / 12 h / 20 °C 4.1: palladium diacetate; N-ethyl-N,N-diisopropylamine; 1,3-bis-(diphenylphosphino)propane / dimethyl sulfoxide / 20 h / 100 °C / Inert atmosphere 4.2: 4 h / Reflux
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