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[ CAS No. 155020-51-2 ]

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Chemical Structure| 155020-51-2
Chemical Structure| 155020-51-2
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Product Details of [ 155020-51-2 ]

CAS No. :155020-51-2 MDL No. :MFCD04115986
Formula : C7H7F2NO Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :159.13 g/mol Pubchem ID :-
Synonyms :

Safety of [ 155020-51-2 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P322-P330-P332+P313-P337+P313-P340-P361-P362-P363-P403-P403+P233-P405-P501 UN#:2811
Hazard Statements:H302-H311-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 155020-51-2 ]

  • Downstream synthetic route of [ 155020-51-2 ]

[ 155020-51-2 ] Synthesis Path-Downstream   1~26

  • 1
  • [ 66684-59-1 ]
  • [ 155020-51-2 ]
YieldReaction ConditionsOperation in experiment
97% With palladium on activated charcoal; hydrogen; In methanol; for 4.5h; Degussa grade Pd/C (1.125 g, 1.058 mmol) was added to a 250 mL round bottom flask previously purged with argon. The Pd was carefully wetted with a few milliliters ofMeOH before the full amount of solvent (42.3 ml) was added. The head space of the flask was evacuated until the solvent began to slightly bubble and then back-filled 3x with N2. <strong>[66684-59-1]2,3-difluoro-1-methoxy-4-nitrobenzene</strong> (2.0 g, 10.58 mmol) was added to the black suspension, and a balloon of H2 gas was attached. The heterogeneous mixture was sparged with H2 for 30 mm, before being allowed to stir under an atmosphere of H2 for anadditional 4 h. The reaction mixture was then filtered over celite to remove Pd/C. The177celite was rinsed with EtOAc, and the filtrate was concentrated to afford Intermediate I-41A(1.63g, 10.24 mmol, 97 %yield) as a purple solid. LC-MS: Method H, RT = 0.83 mm, MS (ESI) m/z: 160.1 (M+H) ?H NMR (400MHz, CHLOROFORM-d) 6.59 (td, J=8.6, 2.2 Hz, 1H), 6.49-6.43 (m, 1H), 3.83 (s, 3H), 3.51 (br. s., 2H).
90% With hydrogenchloride; tin(ll) chloride; In ethanol; water; ethyl acetate; at 20.0℃; for 16.0h; 2, 3-Difluoro-4-methoxyaniline To a mixture of <strong>[66684-59-1]2,3-difluoro-1-methoxy-4-nitrobenzene</strong> 1 (1 equiv.) in EtOH (0.5 M) was added SnCl2 (5 equiv.). Then HCl (25 mL) was added and the reaction was stirred at room temperature for 16 h. Ethyl acetate and H2O were added, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over Na2SO4, and filtered, then the filtrate was concentrated in vacuo to give 2, 3-difluoro-4-methoxyaniline (90%) as a brown solid.
With iron; ammonium chloride; In ethanol; water; at 80.0℃; for 4.0h; Step 1 Preparation of Compound a2 (0413) Compound a1 (3.0g, 16mmol) was dissolved in ethanol (30mL) and water (10mL), and iron (2.7g, 48 mmol) and ammonium chloride (2.6g, 48mmol) were added into the reaction mixture, the reaction mixture was stirred at 80 C for 4 hours. The mixtures are filtered, and water was added into the mother liquor. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The organic layer was condensed under reduced pressure to afford Compound a2 (2.5g) as crude. [M+H]=159.6, Method Condition 4 : retention time 1.07 min
  • 2
  • [ 108-24-7 ]
  • [ 155020-51-2 ]
  • [ 155020-52-3 ]
  • 3
  • [ 771-69-7 ]
  • [ 155020-51-2 ]
  • 4
  • [ 155020-51-2 ]
  • [ 155020-53-4 ]
  • 5
  • [ 155020-51-2 ]
  • [ 1026596-14-4 ]
  • 6
  • [ 155020-51-2 ]
  • [ 155020-46-5 ]
  • 7
  • [ 155020-51-2 ]
  • 7-chloro-4-<3'-<(diethylamino)methyl>-5',6'-difluoro-4'-hydroxyanilino>quinoline [ No CAS ]
  • 8
  • [ 155020-51-2 ]
  • 7-chloro-4-<3'-<(diethylamino)methyl>-2',6'-difluoro-4'-hydroxyanilino>quinoline [ No CAS ]
  • 9
  • [ 155020-51-2 ]
  • 4-Amino-6-diethylaminomethyl-2,3-difluoro-phenol; hydrochloride [ No CAS ]
  • 10
  • [ 155020-51-2 ]
  • [ 940298-94-2 ]
  • 11
  • [ 393-55-5 ]
  • [ 155020-51-2 ]
  • [ 1138820-03-7 ]
YieldReaction ConditionsOperation in experiment
86% As shown in step 1-i of Scheme 1,<strong>[393-55-5]2-fluoronicotinic acid</strong> (8.5 g, 59.0 mmol) was suspended in 100 mL of anhydrous dichloromethane and 0.274 mL of anhydrous DMF. The mixture was cooled to 5C with an ice bath. Oxalyl chloride (5.41 mL, 62.0 mmol) was added dropwise to the cooled mixture. After addition, the mixture was warmed to room temperature and stirred for 15 hours, at which time all solids had gone into solution. The mixture was cooled to 00C and 2,3-difluoro-4-methoxyaniline (Compound 1001, 10.0 g, 62.84 mmol) in 30 mL of DCM was added dropwise. Followed by the dropwise addition of DIEA (20.6 mL, 118.1 mmol). The mixture was warmed to room temperature and stirred for 16 hours, after which time the reaction was quenched with 60 mL of 2M HCl. The organics were washed twice with 50 mL of saturated sodium bicarbonate, once with 50 mL of water, and once with 50 mL of brine. The organics were then dried over anhydrous sodium sulfate, filtered, and evaporated under reduced pressure. The residue was slurried in 350 mL of hexanes, stirred for 30 minutes, collected by vacuum filtration, washed well with hexanes, and dried under vacuum to afford 2-fluoro-N-(2,3-difluoro-4-methoxyphenyl)pyridine-3- carboxamide (Compound 1002, 14.3 g, 86% yield): 1H NuMR (300 MHz, CDCl3) delta 8.68 - 8.62 (m, 2H), 8.40 (dt, J = 4.7, 1.6 Hz, IH), 8.06 - 7.99 (m, IH), 7.44 (td, J = 5.0, 2.5 Hz, IH), 6.82 - 6.75 (m, IH) and 3.91 (d, J = 5.4 Hz, 3H).
  • 12
  • [ 155020-51-2 ]
  • 4-fluoro-5-isopropyl-2-methoxy-3-(4-methylpiperazin-1-yl)-11-oxo-6,11-dihydro-5H-indolo[2,3-b]quinoline-8-carbonitrile [ No CAS ]
  • 13
  • [ 155020-51-2 ]
  • methyl 6-cyano-2-((2,3-difluoro-4-methoxyphenyl)-(isopropyl)amino)-1H-indole-3-carboxylate [ No CAS ]
  • 14
  • [ 155020-51-2 ]
  • 3,4-difluoro-5-isopropyl-2-methoxy-11-oxo-6,11-dihydro-5H-indolo[2,3-b]quinoline-8-carbonitrile [ No CAS ]
  • 15
  • [ 155020-51-2 ]
  • 4-fluoro-5-isopropyl-2-methoxy-3-(4-morpholinopiperidin-1-yl)-11-oxo-6,11-dihydro-5H-indolo[2,3-b]quinoline-8-carbonitrile [ No CAS ]
  • 16
  • [ 155020-51-2 ]
  • 5-cyclobutyl-4-fluoro-2-methoxy-3-(4-morpholinopiperidin-1-yl)-11-oxo-6,11-dihydro-5H-indolo [2,3-b]quinoline-8-carbonitrile [ No CAS ]
  • 17
  • [ 155020-51-2 ]
  • 5-cyclobutyl-3,4-difluoro-2-methoxy-11-oxo-6,11-dihydro-5H-indolo[2,3-b]quinoline-8-carbonitrile [ No CAS ]
  • 18
  • [ 155020-51-2 ]
  • methyl 6-cyano-2-(cyclobutyl(2,3-difluoro-4-methoxyphenyl)amino)-1H-indole-3-carboxylate [ No CAS ]
  • 19
  • [ 155020-51-2 ]
  • 5-cyclobutyl-4-fluoro-2-methoxy-3-(4-methylpiperazin-1-yl)-11-oxo-6,11-dihydro-5H-indolo[2,3-b]quinoline-8-carbonitrile [ No CAS ]
  • 20
  • [ 1191-95-3 ]
  • [ 155020-51-2 ]
  • N-cyclobutyl-2,3-difluoro-4-methoxyaniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With sodium tris(acetoxy)borohydride; acetic acid; In dichloromethane; at 20℃; for 12h; Cyclobutanone (14.0 g, 200 mmol), Acetic acid (1.8 g, 30 mmol), and Sodium triacetoxyborohydride (6.36 g, 30 mmol) were added to a solution of <strong>[155020-51-2]2,3-difluoro-4-methoxyaniline</strong> (3.18 g, 20 mmol) in DCM (120 mL) and the mixture was stirred at RT overnight. Water was added to quench the reaction and the mixture was extracted with DCM. The solvent was removed under and the residue was purified by silica gel chromatography to afford N-cyclobutyl-<strong>[155020-51-2]2,3-difluoro-4-methoxyaniline</strong> (3.82g, 90% yield).MS m/z= 214 [M+H].
  • 21
  • [ 67-64-1 ]
  • [ 155020-51-2 ]
  • 2,3-difluoro-N-isopropyl-4-methoxyaniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With sodium tris(acetoxy)borohydride; acetic acid; In dichloromethane; at 20℃; for 12h; Acetone (11.6 g, 200 mmol), Acetic acid (1.8 g, 30 mmol), and Sodium triacetoxyborohydride (6.36 g, 30 mmol) were added to a solution of <strong>[155020-51-2]2,3-difluoro-4-methoxyaniline</strong> (3.18 g, 20 mmol) in DCM (120 mL) and the mixture was stirred at RT for 12 hr. Water was added to quench the reaction and the mixture was extracted with DCM. The solvent was removed under and the residue was purified by silica gel chromatography to afford 2,3-difluoro-N-isopropyl-4-methoxyaniline. (2.8 g, 70% yield). 1H NMR (400 MHz, CDC13) δ ppm 6.65 (td, J= 8.7, 2.3 Hz, 1H), 6.39 (td, J= 8.7, 2.3 Hz, 1H), 3.85 (s, 3H), 3.58-3.56 (m, 1H), 3.46 (s, 1H), 1.24 (d, J= 6.2 Hz, 6H).
70% With sodium tris(acetoxy)borohydride; acetic acid; In dichloromethane; at 20℃; for 12h; [0154] Acetone (11.6 g, 200 mmol), acetic acid (1.8 g, 30 mmol), and sodium triacetoxyborohydride (6.36 g, 30 mmol) were added to a solution of 2,3-difluoro-4- methoxyaniline (3.18 g, 20 mmol) in DCM (120 mL) and the mixture was stirred at room temperature (RT) for 12 h. Water was added to quench the reaction and the mixture was extracted with DCM. The solvent was removed under and the residue was purified by silica gel chromatography with hexane/ethyl acetate (9/1, v/v) to afford the title compound (2.8 g, 70% yield). 1H NMR (400 MHz, CDC13) δ ppm 6.65 (td, 7 = 8.7, 2.3 Hz, 1H), 6.39 (td, 7 = 8.7, 2.3 Hz, 1H), 3.85 (s, 3H), 3.58-3.56 (m, 1H), 3.46 (s, 1H), 1.24 (d, 7 = 6.2 Hz, 6H).
  • 22
  • [ 7188-38-7 ]
  • [ 100-52-7 ]
  • [ 155020-51-2 ]
  • [ 637-44-5 ]
  • C28H26F2N2O3 [ No CAS ]
  • 23
  • [ 155020-51-2 ]
  • (1s,4s)-4-(8-(2,3-difluoro-4-methoxyphenylamino)-2-(tetrahydro-2H-pyran-4-ylamino)-9H-purin-9-yl)cyclohexanecarboxamide [ No CAS ]
  • 24
  • [ 463-71-8 ]
  • [ 155020-51-2 ]
  • 2,3-difluoro-1-isothiocyanato-4-methoxybenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 2h; 2,3-Difluoro-1-isothiocyanato-4-methoxybenzene To a solution of <strong>[155020-51-2]2,3-difluoro-4-methoxyaniline</strong> (1 equiv.) in DCM (0.8 M) was added DIEA (2.5 equiv.) at 0 C., then SCCl2 (5 equiv.) was added drop-wise at 0 C. The reaction mixture was stirred at room temperature for 2 h. The organic solvent was condensed in vacuo and purified via silica gel to give 2,3-difluoro-1-isothiocyanato-4-methoxybenzene (94%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm: 7.42-7.27 (m, 1H), 7.08 (dt, J=2.1, 8.9 Hz, 1H), 3.99-3.83 (m, 3H).
  • 25
  • [ 79-31-2 ]
  • [ 155020-51-2 ]
  • C11H13F2NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; HATU; In N,N-dimethyl-formamide; at 20℃;Cooling with ice; Step 2 Preparation of Compound a3 (0414) Compound a2 (2.5g, 16mmol) was dissolved in DMF (30mL), and isobutyric acid (1.7g, 19 mmol) ant · O-(7-Azabenzotriazol-1-yl)-1, 1, 3, -tetramethyluronium hexafluorophosphate (7.8g, 21mmol) and triethyl amine (3.1g, 32mmol) was added to the reaction mixture while cooling in ice. The reaction mixture was stirred at room temperature overnight. Water was added into the mixture and the mixture was extracted with diethyl ether. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was condensed under reduced pressure to afford Compound a3 (5.1g) as crude. [M+H]=229.8, Method Condition 4 : retention time 1.54 min
  • 26
  • [ 155020-51-2 ]
  • C19H21FN4O4 [ No CAS ]
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