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[ CAS No. 145369-94-4 ]

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Chemical Structure| 145369-94-4
Chemical Structure| 145369-94-4
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CAS No. :145369-94-4MDL No. :MFCD00272435
Formula : C9H6BrNO Boiling Point : 321.7°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :224.05Pubchem ID :12403680
Synonyms :

Computed Properties of [ 145369-94-4 ]

TPSA : 29.1 H-Bond Acceptor Count : 2
XLogP3 : - H-Bond Donor Count : 1
SP3 : 0.00 Rotatable Bond Count : 0

Safety of [ 145369-94-4 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P280-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 145369-94-4 ]

  • Upstream synthesis route of [ 145369-94-4 ]
  • Downstream synthetic route of [ 145369-94-4 ]

[ 145369-94-4 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 187278-01-9 ]
  • [ 145369-94-4 ]
YieldReaction ConditionsOperation in experiment
87% at 0 - 188℃; for 6.5 h; A mixture of 5-(((4-bromophenyl)amino )methylene)-2,2-dimethyl-1 ,3-dioxane-4, 6-dione (50 g, 154 mmol) in 1,2-dichlorobenzene (500 mL) was stirred at 188°C for 3.5 h. Thereaction was then cooled down to 0°C and stirred further for 3 h. The solid was collected byfiltration, and was then washed with methyl tert-butyl ether (100 mL) to give the title compoundas a brown solid (30.6 g, 87percent). The title compound was characterized by LC-MS and 1H NMRas shown below:LC-MS (ESI, pos. ion) m/z: 224 [M+Ht;1H NMR (400 MHz, CDCh) 8 (ppm): 6.32 (d, J= 7.32 Hz, 1H), 7.48 (d, J= 9.08 Hz, 1H), 7.77(dd, J= 8.88 Hz, 2.32 Hz, 1H), 7.95 (d, J = 7.32 Hz, 1H), 8.34 (d, J = 2.28 Hz, 1H).
87% at 188℃; for 3.5 h; The 5 - (( (4-bromophenyl) amino) methylene) - 2,2-dimethyl -1,3-dioxane -4,6-dione (50g, 154mmol) in 1,2-dichlorobenzene (500 ml) solution is heated to 188 °C, stirring for 3.5 hours, cooling to 0 °C, continue to stir 3 hours. Filtering, collecting solid, solid after armoruncle ether (100 ml) eluting, to obtain the title compound as brown solid (30.6g, 87percent).
29.9 g at 190℃; for 0.25 h; Diphenyl ether (519.9 g, 3.064 mol)Add to a 1000 mL three-necked flask,Preheat to 190 ° C,Compound 2a (50.1 g, 0.153 mol) was added slowly,Reaction for 15 min.TLC detection [V (dichloromethane): V (methanol) = 15:1] reaction junctionbundle,cool down,The reaction solution was poured into 600 mL of petroleum ether and stirred.Precipitating solids,Filtering,dry,Made a grayish yellow solid 29.9g,
Reference: [1] Patent: WO2014/22128, 2014, A1, . Location in patent: Paragraph 0144; 0145; 0154
[2] Patent: CN103539777, 2016, B, . Location in patent: Paragraph 0276; 0319; 0320
[3] Archiv der Pharmazie, 2018, vol. 351, # 6,
[4] Molecules, 2018, vol. 23, # 7,
[5] Patent: CN108456165, 2018, A, . Location in patent: Paragraph 0047; 0077-0078
  • 2
  • [ 98948-95-9 ]
  • [ 145369-94-4 ]
YieldReaction ConditionsOperation in experiment
95% for 9 h; Heating / reflux The solid 6-bromo-4-hydroxy-quinoline-3-carboxylic acid (102.59 g, 337.7 mmol) was added to hot diphenyl ether (508 g) and then the mixture was heated to reflux for 9 h to afford a light brown suspension.
After cooling to room temperature, the mixture was diluted with methanol (20 mL) and diethyl ether (300 mL).
Then, the solids were collected by filtration and washed with diethyl ether.
After drying in air, 72.43 g (95percent yield) of 6-bromo-quinolin-4-ol was isolated as a white solid: EI-HRMS m/e calcd for C9H6BrNO (M+) 222.9633, found 222.9630.
90% for 0.5 h; Reflux . Deprotection and removal of the carboxylic acid
90% for 0.5 h; Reflux 10558] The bicyclic compound 3-2 is prepared from bromoaniline 3-1 using diethyl 2-(ethoxymethylene)malonate or a similar reagent. Deprotection and removal of the carboxylic acid, followed by halogenation using a reagent such as phosphorus oxychloride yields compound 3-5. Derivatization with pyridine boronate in Suzuki coupling conditions yields 3-6, which is reacted in a second Suzuki reaction with a benzothiazolyl boronate to yield compound 3-7. Subsequent heating in hydrochloric acid in a solvent such as methanol results in removal of an acetyl group.
77% at 260℃; for 2 h; 4.1.7
6-Bromoquinolin-4-ol (10)
6-Bromo-4-hydroxyquinoline-3-carboxylic acid (9) (5.0 g, 18.73 mmol) was added to a 100 mL round-bottomed flask in Ph2O (30 mL) and then stirred at 260 °C for 2 h.
After cooling to 60 °C, 30 mL petroleum ether was added and the suspended solid was filtered, washed with petroleum ether, EtOAc and dried under reduced pressure to give the title compound (3.21 g, 14.39 mmol, 77percent yield) as a brown solid. ESI-MS: m/z = 224 [M+H]+.

Reference: [1] ChemMedChem, 2015, vol. 10, # 5, p. 836 - 849
[2] Patent: US2006/63805, 2006, A1, . Location in patent: Page/Page column 9
[3] Patent: WO2012/116237, 2012, A2, . Location in patent: Page/Page column 120
[4] Patent: US2015/320727, 2015, A1, . Location in patent: Paragraph 0557; 0558
[5] European Journal of Medicinal Chemistry, 2015, vol. 99, p. 36 - 50
[6] Journal of the Chemical Society, 1950, p. 384,389
[7] Tetrahedron Letters, 2008, vol. 49, # 19, p. 3137 - 3141
[8] Patent: WO2014/151147, 2014, A1, . Location in patent: Paragraph 00641
[9] Patent: US2015/30588, 2015, A1, . Location in patent: Page/Page column 77
[10] Patent: US9295673, 2016, B2, . Location in patent: Page/Page column 365; 366
[11] Patent: WO2006/132739, 2006, A2, . Location in patent: Page/Page column 44-45
  • 3
  • [ 76228-06-3 ]
  • [ 145369-94-4 ]
YieldReaction ConditionsOperation in experiment
86%
Stage #1: With sulfuric acid In acetonitrile for 0.333333 h;
Stage #2: With potassium permanganate In acetonitrile at 85℃; for 5 h;
Add 6-bromo-4-oxo-2,3-dihydroquinoline (0.01 mol) to a 25 ml reaction flask, add 15 ml of acetonitrile, concentrated sulfuric acid (0.02 mol), stir for 20 minutes, and slowly add potassium permanganate. (0.02 mol), the reaction was stirred at 85 ° C, the progress of the reaction was monitored by TLC, and the reaction was stopped after 5 hours. After the reaction solution is cooled to room temperature, it is poured into 50 ml of water, stirred and filtered to obtain a crude product of 6-bromo-4-hydroxyquinoline, which is separated by silica gel column chromatography (column chromatography silica gel 100-200 mesh, eluent oil) Ether: ethyl acetate = 1:4). The eluent was concentrated to give the product. The yield was 86percent, and the purity was 96percent
Reference: [1] Patent: CN108794396, 2018, A, . Location in patent: Paragraph 0019
  • 4
  • [ 1551219-53-4 ]
  • [ 145369-94-4 ]
YieldReaction ConditionsOperation in experiment
83.5% at 220℃; for 0.0833333 h; Compound 1g (47.9 mmol, 10 g) was dissolved in diphenyl oxide and heated to 220 ℃ for 5 min. After cooling, the precipitated solid was filtered and washed with petroleum ether. Yield 83.5percent. HPLC purity: 96.7percent.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 3, p. 799 - 807
  • 5
  • [ 106-40-1 ]
  • [ 145369-94-4 ]
Reference: [1] Journal of the Chemical Society, 1950, p. 384,389
[2] Patent: WO2012/116237, 2012, A2,
[3] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 3, p. 799 - 807
[4] Patent: WO2014/22128, 2014, A1,
[5] Patent: WO2014/151147, 2014, A1,
[6] Patent: US2015/30588, 2015, A1,
[7] ChemMedChem, 2015, vol. 10, # 5, p. 836 - 849
[8] European Journal of Medicinal Chemistry, 2015, vol. 99, p. 36 - 50
[9] Patent: US2015/320727, 2015, A1,
[10] Patent: US9295673, 2016, B2,
[11] Patent: CN103539777, 2016, B,
[12] Molecules, 2018, vol. 23, # 7,
[13] Patent: WO2006/132739, 2006, A2,
  • 6
  • [ 10174-70-6 ]
  • [ 145369-94-4 ]
Reference: [1] Patent: US5153196, 1992, A,
  • 7
  • [ 2033-24-1 ]
  • [ 106-40-1 ]
  • [ 145369-94-4 ]
Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 6, p. 2232 - 2235
  • 8
  • [ 122794-99-4 ]
  • [ 145369-94-4 ]
Reference: [1] Journal of the Chemical Society, 1950, p. 384,389
[2] Patent: WO2012/116237, 2012, A2,
[3] Patent: WO2014/151147, 2014, A1,
[4] Patent: US2015/30588, 2015, A1,
[5] ChemMedChem, 2015, vol. 10, # 5, p. 836 - 849
[6] European Journal of Medicinal Chemistry, 2015, vol. 99, p. 36 - 50
[7] Patent: US2015/320727, 2015, A1,
[8] Patent: US9295673, 2016, B2,
[9] Patent: WO2006/132739, 2006, A2,
  • 9
  • [ 101937-44-4 ]
  • [ 145369-94-4 ]
Reference: [1] Journal of the Chemical Society, 1950, p. 384,389
[2] ChemMedChem, 2015, vol. 10, # 5, p. 836 - 849
[3] European Journal of Medicinal Chemistry, 2015, vol. 99, p. 36 - 50
  • 10
  • [ 145369-94-4 ]
  • [ 65340-70-7 ]
YieldReaction ConditionsOperation in experiment
98.5% for 6 h; Heating / reflux The solid 6-bromo-quinolin-4-ol (52 g, 232.1 mmol) was added to phosphorus oxychloride (213.5 mL) and then the mixture was heated to reflux for 6 h to afford a light brown solution.
After cooling to room temperature, the excess phosphorus oxychloride was removed under the vacuum.
The remaining residue was poured into an ice-containing beaker (2 L).
Then, it was slowly neutralized with solid potassium carbonate and the resulting solids were collected by filtration and washed with water.
After drying in air, 55.46 g (98.5percent yield) of 6-bromo-4-chloro-quinoline was isolated as a light yellow solid: EI-HRMS m/e calcd for C9H5BrClN (M+) 240.9294, found 240.9297.
93% for 1.5 h; Reflux 10558] The bicyclic compound 3-2 is prepared from bromoaniline 3-1 using diethyl 2-(ethoxymethylene)malonate or a similar reagent. Deprotection and removal of the carboxylic acid, followed by halogenation using a reagent such as phosphorus oxychloride yields compound 3-5. Derivatization with pyridine boronate in Suzuki coupling conditions yields 3-6, which is reacted in a second Suzuki reaction with a benzothiazolyl boronate to yield compound 3-7. Subsequent heating in hydrochloric acid in a solvent such as methanol results in removal of an acetyl group.
84% With trichlorophosphate In N,N-dimethyl-formamide at 120℃; for 5 h; 4.1.8
6-Bromo-4-chloroquinoline (11)
To a 100 mL round-bottomed flask was added 6-bromoquinolin-4-ol (10) (3.0 g, 13.45 mmol), POCl3 (20 mL) and DMF (0.5 mL).
The mixture was stirred at reflux for 6 h.
After cooling to room temperature, the reaction mixture was poured into ice water (100 mL) and stirred for 1 h.
Then the pH of the mixture was adjusted to 8 using saturated aqueous NaHCO3.
The mixture was extracted with EtOAc and the organic phase was dried over sodium sulfate and concentrated in vacuo to give the title compound (2.75 g, 11.36 mmol, 84percent yield) as a white solid. 1H NMR (500 MHz, DMSO-d6) δ 8.87 (d, J = 4.5 Hz, 1H, Ar-H), 8.32 (d, J = 2.0 Hz, 1H, Ar-H), 8.03 (d, J = 9.0 Hz, 1H, Ar-H), 7.99 (dd, J = 9.0, 2.0 Hz, 1H, Ar-H), 7.82 (d, J = 4.5 Hz, 1H, Ar-H). ESI-MS: m/z = 242 [M+H]+.
84%
Stage #1: Heating / reflux
6-Bromo-4-chloroquinoline. The solution of the compound from Example 17b (2 g, 8.9 mmol) in POCI3 (10 mL) was refluxed overnight, cooled and quenched by ice water. The precipitate was collected, washed with H2O and dried in vacuo to afford the title compound as a grey solid (1.8 g, 84percent). 1 H NMR (400 MHz, DMSO-CZ6) δ ppm 8.90 (d, J=4.80 Hz, 1 H) 8.37 (d, J=2.02 Hz, 1 H) 8.07 (d, J=8.59 Hz, 1 H) 8.03 (dd, J=8.84, 2.02 Hz, 1 H) 7.86 (d, J=4.55 Hz, 1 H).
32% With trichlorophosphate In toluene at 115℃; for 4 h; To a suspension of 6-bromo-4-hydroxyquinolin (14.55 g, 64.9 mmol) in toluene (20mL) was added POCh (6.05 mL, 64.9 mmol) slowly. The reaction was stirred at 115°C for 4 h,then cooled down to 0°C and diluted with DCM (400 mL). The mixture was washed with 4MNaOH (70 mL) followed by brine (100 mL), dried over anhydrous Na2S04 and concentrated invacuo. The residue was recrystallized in n-heptane (150 mL) to give the title compound as ayellow solid (5.5 g, 32percent). The title compound was characterized by LC-MS and 1H NMR asshown below:LC-MS (ESI, pos. ion) m/z: 242 [M+Ht;1H NMR (400 MHz, CDCh) 8 (ppm): 7.50 (d, J= 4.72 Hz, 1H), 7.82 (dd, J= 8.96 Hz, 2.16 Hz,1H), 7.98 (d, J= 8.92 Hz, 1H), 7.95 (d, J= 2.16 Hz, 1H), 8.34 (d, J= 4.68 Hz, 1H).
32% With trichlorophosphate In toluene at 115℃; for 4 h; To 6-bromo-4-hydroxyquinoline (14.55g, 64 . 9mmol) toluene (20 ml) is slowly added in solution POCl 3 (6.05 ml, 64 . 9mmol). responds the fluid in 115 °C stirring 4 hours, cooling to 0 °C, and added DCM (400 ml) dilution. The resulting mixed solution for sequentially 4MNaOH aqueous solution (70 ml) and the brine (100 ml) washing, anhydrous Na 2 SO 4 drying, and concentrated under reduced pressure. In normal heptane of the residue (150 ml) is recrystallized in, to obtain the title compound as yellow solid (5.5g, 32percent).

Reference: [1] Patent: US2006/63805, 2006, A1, . Location in patent: Page/Page column 9
[2] ChemMedChem, 2015, vol. 10, # 5, p. 836 - 849
[3] Patent: US2015/320727, 2015, A1, . Location in patent: Paragraph 0557; 0558
[4] European Journal of Medicinal Chemistry, 2015, vol. 99, p. 36 - 50
[5] Patent: WO2006/132739, 2006, A2, . Location in patent: Page/Page column 48
[6] Patent: WO2014/22128, 2014, A1, . Location in patent: Paragraph 0144; 0145; 0155
[7] Patent: CN103539777, 2016, B, . Location in patent: Paragraph 0276; 0323; 0324
[8] Journal of the Chemical Society, 1950, p. 384,389
[9] Patent: WO2012/116237, 2012, A2, . Location in patent: Page/Page column 120
[10] Patent: WO2011/84402, 2011, A1, . Location in patent: Page/Page column 144-145
[11] European Journal of Medicinal Chemistry, 2014, vol. 75, p. 96 - 105
[12] Journal of the Brazilian Chemical Society, 2014, vol. 25, # 5, p. 980 - 986
[13] Patent: WO2014/151147, 2014, A1, . Location in patent: Paragraph 00641
[14] Patent: US2015/30588, 2015, A1, . Location in patent: Page/Page column 77; 78
[15] Patent: US9295673, 2016, B2, . Location in patent: Page/Page column 366
  • 11
  • [ 145369-94-4 ]
  • [ 65340-70-7 ]
YieldReaction ConditionsOperation in experiment
92.6% With phosphorus trichloride In toluene for 2 h; Reflux willL0g (44.63 mol) of 6-bromoquinolin-4 (1H) -one, 100 ml of toluene and 12.25 g (89.26 mol) of phosphorus trichloride were added to a 250 ml three-necked flask and heated to reflux for 2 hours. , Dried and dried. The solid was beaten with ether (100 ml), filtered and dried to give a yellow powder (yield 92.6percent).
85% for 3 h; Heating / reflux Diphenyl ether (80 ml) was added to 4-bromoaniline (4.5 g) and 5-(methoxymethylene)-2,2-dimethyl-1,3-dioxan-4,6-dione (5.4 g), and the mixture was stirred at 80°C for one hr. Biphenyl (24.2 g) was added thereto, and the mixture was stirred at 220°C for 3 hr. The reaction mixture was cooled to room temperature, and diethyl ether was added to the cooled mixture. The precipitated crystal was collected by filtration and was washed with diethyl ether. The residue was purified by column chromatography with a hexane-acetone system to give 6-bromoquinolone (1.57 g, yield 27percent). Thionyl chloride (5 ml) and a minor amount of dimethylformamide were added to 6-bromoquinolone (1.6 g), and the mixture was stirred under reflux for 3 hr. The reaction mixture was added to a saturated aqueous sodium bicarbonate solution under ice cooling, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography with a hexane-ethyl acetate system to give 6-bromo-4-chloroquinoline (1.43 g, yield 85percent).
70% With trichlorophosphate In N,N-dimethyl-formamide for 2 h; Reflux A mixture of 4 (17.0 g, 131.5 mmol), POCl3 (180 mL) and anhydrous DMF (18 mL) was stirred and heated at reflux for 2 h. After removal of POCl3, the residue was poured into ice water and extracted with EtOAc. The combined organic layers were washed with saturated aqueous NaHCO3, brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified by silica gel column chromatography (4:1 hexanes/EtOAc) to afford 5 (12.8 g, 70percent) as a white solid, mp 111-112 °C (lit31 111-112 °C). 1H NMR (CDCl3) δ 8.79 (d, J = 5.0 Hz, 1H, Ar-H), 8.40 (d, J = 2.5 Hz, 1H, Ar-H), 8.00 (d, J = 9.0 Hz, 1H, Ar-H), 7.84 (dd, J = 9.0, 2.0 Hz, 1H, Ar-H), 7.52 (d, J = 5.0 Hz, 1H, Ar-H).
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 14, p. 5522 - 5537
[2] Patent: CN106432073, 2017, A, . Location in patent: Paragraph 0026; 0027; 0036; 0037; 0045; 0046; 0056; 0057
[3] Patent: EP1724268, 2006, A1, . Location in patent: Page/Page column 41-42
[4] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1569 - 1574
  • 12
  • [ 145369-94-4 ]
  • [ 853908-50-6 ]
YieldReaction ConditionsOperation in experiment
64.5% for 2 h; Synthesis of Compound 3a (29.0 g, 0.130 mol)Add to a 500 mL three-necked flask,Heat and stir until dissolved.Further, a mixture of nitric acid (40.95 g, 0.650 mol) and propionic acid (10 mL) was slowly added dropwise to the reaction flask.After the addition is completed, the reaction is further carried out for 2 hours.TLC detection [V (dichloromethane): V (methanol) = 15:1] The reaction was completed, cooled, filtered,The filter residue is added to the ice saturated sodium bicarbonate solution and stirred.Filtered,The residue is dry,The compound was obtained as a yellow solid (26.0 g, yield: 64.5percent).
50.2% With nitric acid In propionic acid at 125℃; for 2 h; The solution of compound 2g (20 mmol, 4.48 g) in propionic acid (30 mL) was heated to 125 ℃ and the mixture of nitric acid (0.89 mL) and propionic acid (6.27 mL) was added dropwise for 1 h. Then the mixture was reacted for 1 h and precipitated by petroleum ether. The solid was filtered and washed with diethyl ether. Yield 50.2percent. HPLC purity: 98.1percent.
Reference: [1] Patent: CN108456165, 2018, A, . Location in patent: Paragraph 0047; 0079-0080
[2] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 3, p. 799 - 807
[3] Archiv der Pharmazie, 2018, vol. 351, # 6,
[4] Molecules, 2018, vol. 23, # 7,
  • 13
  • [ 145369-94-4 ]
  • [ 723281-72-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 3, p. 799 - 807
[2] Molecules, 2018, vol. 23, # 7,
[3] Archiv der Pharmazie, 2018, vol. 351, # 6,
[4] Patent: CN108456165, 2018, A,
  • 14
  • [ 145369-94-4 ]
  • [ 874792-20-8 ]
Reference: [1] Patent: WO2011/84402, 2011, A1,
  • 15
  • [ 145369-94-4 ]
  • [ 916812-31-2 ]
Reference: [1] Patent: WO2006/132739, 2006, A2,
  • 16
  • [ 145369-94-4 ]
  • [ 1086062-66-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1569 - 1574
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