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Product Details of [ 55934-22-0 ]

CAS No. :55934-22-0 MDL No. :MFCD09475797
Formula : C10H7Cl2NO Boiling Point : -
Linear Structure Formula :- InChI Key :XHKVDLMHZLUDSK-UHFFFAOYSA-N
M.W : 228.07 Pubchem ID :22832054
Synonyms :

Safety of [ 55934-22-0 ]

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

Application In Synthesis of [ 55934-22-0 ]

* 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 [ 55934-22-0 ]

[ 55934-22-0 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 99074-22-3 ]
  • [ 55934-22-0 ]
YieldReaction ConditionsOperation in experiment
With trichlorophosphate
  • 2
  • [ 141-82-2 ]
  • [ 536-90-3 ]
  • [ 55934-21-9 ]
  • [ 55934-22-0 ]
YieldReaction ConditionsOperation in experiment
4% With trichlorophosphate for 3h; Heating;
1: 0.7 g 2: 1.3 g Stage #1: malonic acid; m-Anisidine With trichlorophosphate at 105℃; for 1h; Stage #2: With trichlorophosphate for 3h; Reflux; Overall yield = 38.6 %; Overall yield = 3 g; regioselective reaction; 2 Preparation of 2,4-dichloro-5-methoxyquinoline & 2,4-dichloro-7-methoxyquinoline POCl3(4.16 ml, 44.7 mmol) was added to the mixture of 3-methoxy aniline (5.0 g, 40.6 mmol) and malonic acid (4.22 g, 40.6 mmol). The reaction mass was heated to 105° C. for 1 h. The reaction mass was diluted with water (20 ml) and stirred for 30 min. The precipitated solid was filtered and washed with water. 2N NaOH solution (30 ml) was added to the solid and stirred for 18 hr. The remaining solid was filtered off and ethanol (5 ml) was added to the filtrate was acidified to PH 2 using conc. HCl. The precipitated solid was filtered and washed with water. The solid was dried under reduced pressure to get desired regio isomer in the ratio 50:50 (3 g, 38.6%) as white solid.1H NMR (400 MHz, DMSO): δ ppm 11.27-11.07 (m, 3H), 10.01 (s, 1H), 7.68-7.65 (d, J=12 Hz, 1H), 7.41 (t, J=12 Hz, 1H) 6.91-6.88 (d, J=12 Hz, 1H), 6.76-6.72 (m, 3H), 5.62-5.60 (d, J=8 Hz, 2H), 3.92 (s, 3H), 3.72 (s, 3H). A solution of 4-hydroxy-5-methoxyquinoline-2(1H)-one & 4-hydroxy-7-methoxyquinoline-2(1H)-one (3 g, 15.70 mmol) in POCl3(3.66 ml, 39.2 mmol) was refluxed for 3 h. The solvent was evaporated under reduced pressure and the residue was diluted with cold water. The aqueous solution was basified by solid sodium carbonate and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography (20% ethyl acetate in pet ether) to afford mixture of regioisomers. This mixture of regioisomers was separated by SFC purification to afford 2,4-dichloro-5-methoxyquinoline (0.7 g, 39%) and 2,4-dichloro-7-methoxyquinoline (required isomer) (1.3 g, 72.6%) as white solid. 2,4-dichloro-7-methoxyquinoline:1H NMR (400 MHz, CDCl3): δ ppm 8.07-8.04 (d, J=12 Hz, 1H), 7.35-7.34 (m, 2H), 7.28-7.26 (m, 1H), 3.94 (s, 3H); 2,4-dichloro-5-methoxyquinoline:1H NMR (400 MHz, CDCl3): δ ppm 7.66-7.60 (m, 2H), 7.40 (m, 1H), 7.25 (s, 1H), 6.95-6.93 (d, J=8 Hz, 1H), 3.97 (s, 3H).
  • 3
  • [ 55934-22-0 ]
  • [ 33513-42-7 ]
  • [ 419566-55-5 ]
YieldReaction ConditionsOperation in experiment
60% With trichlorophosphate Heating;
  • 4
  • [ 141-82-2 ]
  • [ 536-90-3 ]
  • [ 55934-22-0 ]
YieldReaction ConditionsOperation in experiment
70% With trichlorophosphate Heating;
With trichlorophosphate at 100 - 105℃; for 15h; 1 Preparation of 2,4-dichloro-7-methoxy-quinoline:1. Charged m-anisidine, malonic acid and POCl3 into 500 mL jacketed reactor.2. Stirred the mixture at reflux (100-1050C) for 10-15h.3. Poured the mixture into ice-water (2.2 Lt) slowly while keeping the temperature below 300C.4. Filtered solid and rinsed with water and air dried for 2h.5. Dissolved solids in EtOAc (400 mL) at 500C and then filtered through a pad of silica gel and charcoal and rinsed with 1:1 mixture of EtOAc/hexane (300 mL).6. Distilled EtOAc up to minimum volume of 200 mL then added hexane (100 mL) slowly and then stirred at room temperature for 2h.7. Filtered the solids, rinsed with EtOAc/hexane (1:1 mixture, 75 mL) and air dried for 2h and then at 500C for 12h to afford the product in the following batches. 1st crop: 11.4 g, 97.01% pure. 2nd crop: 2.7g, 95.3 % pure.
With trichlorophosphate at 20℃; for 5.25h; Reflux; 2 2,4-DICHLORO-7-METHOXYQUINOLINE. Phosphorus(V)oxychloride (20 mL, 1.3 M) was added through a running condenser into a 3-neck round bottom flask equipped with a stir bar containing malonic acid (2.710 g, 26.00 mmol) at room temperature. While stirring, m-anisidine (4.000 g, 32.48 mmol) was added in small portions over a period of 15 minutes through an open neck of the round bottom flask. The reaction mixture was heated and stirred at reflux for 5 hours. The reaction mixture was allowed to cool to room temperature before it was poured over crushed ice (350 mL). The pH of the resulting aqueous solution was adjusted to 10 with concentrated ammonium hydroxide. The aqueous suspension was extracted with dichloromethane. The combined organic layers were dried over MgSO4 and filtered before concentration to provide a 2.2:1 mixture (1H NMR) of the 7-methoxy and 5-methoxy regioisomers. Purification by column chromatography (0-8% ethyl acetate in hexanes) yielded a white solid (3.181 g, 54%) that was recrystallized from ethyl acetate and hexanes to provide the 7-methoxy isomer. Mp 131.5-132.5° C.; Rf=0.18 (5% EtOAc/hexanes); IR (film) 3092, 2982, 1623, 1572, 1559 cm-1; 1H NMR (400 MHz, CDCl3) δ 8.01 (d, J=9.2 Hz, 1H), 7.32 (s, 1H), 7.31 (d, J=2.4 Hz, 1H), 7.23 (dd, J=9.2, 2.4 Hz, 1H), 3.92 (s, 3H); 13C NMR (100 MHz, CDCl3) ppm 162.2, 150.2, 150.0, 143.9, 125.2, 120.7, 120.1, 119.5, 107.1, 55.7; HRMS submitted.
With trichlorophosphate at 120℃; for 16h;

  • 5
  • [ 55934-22-0 ]
  • [ 419566-63-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 60 percent / phosphorous oxychloride / Heating 2: 60 percent / aq. hydrochloric acid / Heating 3: 75 percent / ammonia (g) / ethanol / 0 - 20 °C
  • 6
  • [ 55934-22-0 ]
  • 3-methoxy-8,9,10,11-tetrahydro-5<i>H</i>-dibenzo[<i>b</i>,<i>h</i>][1,6]naphthyridin-6-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 60 percent / phosphorous oxychloride / Heating 2: 60 percent / aq. hydrochloric acid / Heating 3: 75 percent / ammonia (g) / ethanol / 0 - 20 °C 4: 75 percent / sulfuric acid; acetic acid / Heating
  • 7
  • [ 288-13-1 ]
  • [ 55934-22-0 ]
  • [ 918662-51-8 ]
YieldReaction ConditionsOperation in experiment
56% at 80 - 115℃; for 3h; 16.2 Solid pyrazole (3.2 g, 47.36 mmol, 3.0 equiv.) was heated and melted at 80 0C. Then solid 2,4-Dichloro-7-methoxy-quinoline (3.6 g, 15.78 mmol, 1.0 equiv.) was added and the mixture was then heated to 115 0C fo 3 h. Then the mixture was cooled to rt and purified by flash chromatography (20% ethyl acetate/hexane) to give 4-Chloro-7-methoxy-2-pyrazol- 1-yl-quinoline (2.3 g, 8.88 mmol, 56% yield) as white solid. 1H NMR (CDCl3): 8.77 (d, 1 H, J= 2.8 Hz); 8.18 (s, 1 H); 8.10 (d, 1 H, J= 9.2 Hz); 7.79 (s, 1 H); 7.38 (d, 1 H, J= 2.8 Hz); 7.23 (dd, 1 H, J= 2.0, 8.8 Hz); 6.53-6.52 (m, 1 H); 3.98 (s, 3 H). MS m/z 260 (M++H).
56% at 80 - 115℃; for 3h; 3 Preparation of 4-Chloro-7-methoxy-2-(1H-pyrazol-1-yl) quinoline Solid pyrazole (3.2 g, 47.36 mmol) was heated to 80° C. Then 2,4-Dichloro-7-methoxyquinoline (3.6 g, 15.78 mmol) was added. The reaction mass was heated to 115° C. for 3 hr. The reaction mass was cooled to RT and was purified by silica gel chromatography (20% ethyl acetate in pet ether) to get desired compound (2.3 g, 56%) as white solid.1H NMR (400 MHz, CDCl3): δ ppm 8.77 (d, J=2.8 Hz, 1H), 8.18 (s, 1H), 8.10 (d, J=9.2 Hz, 1H), 7.79 (s, 1H), 7.38 (d, J=2.8 Hz, 1H), 7.23 (dd, J=2.0, 8.8 Hz, 1H), 6.53-6.52 (m, 1H), 3.98 (s, 3H); MS: MS m/z 260.0 (M++1).
  • 8
  • [ 27037-34-9 ]
  • [ 55934-22-0 ]
YieldReaction ConditionsOperation in experiment
60 - 82% A suspension of 4-hydroxy-7-methoxy-2-oxo-l,2-dihydroquinoline (Faber K. etal, J. Heterocyclic chem., 1985 22, 1080) (5.0 g, 26.17 mmol) in POCl3 (25 mL, 261.7 mmol) was heated at 115 0C for 3 h (clear solution obtained upon heating). After 3 h, the reaction mixture was concentrated under reduced pressure. The residue was poured into iced water (40 mL), pH was then adjusted to 10 with 3N NaOH and extracted with CHCl3 (3 x 100 mL). The combined CHCl3 layers were washed with brine and dried (MgSO4). The organic layer EPO <DP n="73"/>was then filtered and concentrated to give 2,4-Dichloro-7-methoxy-quinoline (4.9 g, 21.49 mmol, 82percent yield) as brown solid. MS m/z 229 (M++..).
  • 9
  • [ 55934-22-0 ]
  • [ 1254256-54-6 ]
YieldReaction ConditionsOperation in experiment
90% With N-Bromosuccinimide; trifluoroacetic acid In dichloromethane at 0 - 20℃; for 2h; 2 Step 2 - Preparation of 8-bromo-2,4-dichloro-7-methoxy-quinoline1. Charged 2,4-dichloro-7-methoxy quinoline (31.05 g, 136 mmol) and methylene chloride (620 mL).2. Cooled the mixture to 00C and charged TFA (2.5 eq) and NBS (1.15 eq) and then warmed the mixture to room temperature.3. Stirred at room temperature for 2h.4. Quenched with IM NaOH (~ 349 mL, 40 mmol) to adjust the pH to 7 and separated the layers.5. Washed with water (403 mL) and allowed the layers to separate. Collected organic layer.6. Distilled solvent using rotovap under reduced pressure and solvent switched to IPA (250 mL).7. Heated to 700C and then cooled to 22°C over 2h and treated with IM NaOH (88mL, 0.5eq) at room temperature and stirred for 30 min.8. Filtered and rinsed with 1 :3 mixture of IP A/Water (100 mL) and water (250 mL) and dried under vacuum at 500C to afford 37.62 g of product (90% yield) as beige/tan solid. HPLC area % purity: ~ 95.1%.
  • 10
  • [ 55934-22-0 ]
  • [ 20439-47-8 ]
  • [ 1353892-02-0 ]
YieldReaction ConditionsOperation in experiment
68% With sodium t-butanolate In α,α,α-trifluorotoluene at 100℃; for 0.166667h; Microwave irradiation; 2 H,4CL6,7(MEO)2QUIN-BAM. A 10-20 mL μW vial was charged with (R,R)-diaminocyclohexane (442.4 mg, 3.874 mmol), 2,4-dichloro-6,7-dimethoxyquinoline (2.000 g, 7.749 mmol), Pd(dba)2 (44.5 mg, 77.48 μmol), rac-BINAP (48.2 mg, 77.48 μmol), and sodium tert-butoxide (1.117 g, 11.62 mmol). Trifluoromethylbenzene (13.4 mL) was added and the resulting suspension was heated at 100° C. and stirred in the microwave for 10 min. The reaction mixture was filtered through celite with CH2Cl2 and concentrated. The residue was triturated with ethyl acetate and hexanes to provide a light brown powder (1.4612 g, 68%) that was sufficiently pure by 1H NMR; [α]D20 +410 (c 0.10, CHCl3); Rf=0.15 (50% EtOAc/hexanes); IR (film) 3223, 2930, 1600 cm-1; 1H NMR (400 MHz, CDCl3, 330 K) δ 7.24 (s, 2H), 7.09 (s, 2H), 6.32 (br s, 2H), 5.50 (br s, 2H), 4.02 (s, 6H), 4.00 (br s, 2H), 3.97 (s, 6H), 2.38-2.28 (m, 2H), 1.90-1.80 (m, 2H), 1.55-1.35 (m, 4H); 13C NMR (100 MHz, CDCl3, 330 K) ppm 156.2, 153.2, 147.1, 145.3, 141.0, 115.7, 109.2, 106.6, 103.6, 56.2 (2C), 56.1, 33.0, 24.9; HRMS (CI): Exact mass calcd for C28H31Cl2N4O4[M+H]+ 557.1717. found 557.1717.
  • 11
  • [ 55934-22-0 ]
  • [ 20439-47-8 ]
  • [ 1353892-01-9 ]
YieldReaction ConditionsOperation in experiment
76% With sodium t-butanolate In α,α,α-trifluorotoluene at 100℃; for 0.166667h; Microwave irradiation; 2 H,4CL7MEOQUIN-BAM. A 2-5 mL μW vial was charged with (R,R)-diaminocyclohexane (125.2 mg, 1.096 mmol), 2,4-dichloro-7-methoxyquinoline (500 mg, 2.190 mmol), Pd(dba)2 (12.6 mg, 22.0 μmol), rac-BINAP (13.6 mg, 22.0 μmol), and sodium tert-butoxide (316.2 mg, 3.290 mmol). Trifluoromethylbenzene (3.8 mL) was added and the resulting suspension was heated at 100° C. and stirred in the microwave for 10 min. The reaction mixture was diluted with CH2Cl2 and filtered through Celite. The filtrate was concentrated and washed with CH2Cl2 then hexanes to provide a light brown powder (412.9 mg, 76%) that was pure by 1H NMR; [α]D20 +580 (c 0.19, CHCl3); Rf=0.25 (50% EtOAc/hexanes); IR (film) 3220, 2933, 1610, 1510 cm-1; 1H NMR (500 MHz, CDCl3, 325 K) δ 7.82 (d, J=9.0 Hz, 2H), 7.08 (s, 2H), 6.91 (dd, J=9.0, 2.5 Hz, 2H), 6.31 (br s, 2H), 5.64 (br s, 2H), 4.09 (br s, 2H), 3.94 (s, 6H), 2.41-2.32 (m, 2H), 1.90-1.80 (m, 2H), 1.55-1.38 (m, 4H); 13C NMR (100 MHz, CDCl3, 325 K) ppm 162.0, 157.3, 150.5, 142.3, 125.3, 116.3, 114.4, 109.5, 106.0, 56.1, 55.5, 32.9, 24.9; HRMS (ESI): Exact mass calcd for C26H27Cl2N4O2 [M+H]+ 497.1511. found 497.1501.
  • 12
  • [ 55934-22-0 ]
  • [ 1353891-48-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium t-butanolate / 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0) / α,α,α-trifluorotoluene / 0.17 h / 100 °C / Microwave irradiation 2: 0.67 h / 180 °C / Microwave irradiation
  • 13
  • [ 55934-22-0 ]
  • [ 1353891-45-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium t-butanolate / 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0) / α,α,α-trifluorotoluene / 0.17 h / 100 °C / Microwave irradiation 2: α,α,α-trifluorotoluene / 0.33 h / 220 °C / Microwave irradiation
  • 14
  • [ 55934-22-0 ]
  • [ 918662-51-8 ]
YieldReaction ConditionsOperation in experiment
With NH-pyrazole In ethyl acetate 3 Step 3: Step 3: Preparation of 4-Chloro-7-methoxy-2-(1H-pyrazol-1-yl)quinoline Solid pyrazole (3.2 g, 47.36 mmol) was heated to 80° C. Then 2,4-Dichloro-7-methoxyquinoline (3.6 g, 15.78 mmol) was added. The reaction mass was heated to 115° C. for 3 hr. The reaction mass was cooled to RT and was purified by silica gel chromatography (20% ethyl acetate in pet ether) to get desired compound (2.3 g, 56%) as white solid. 1H NMR (400 MHz, CDCl3): δ ppm 8.77 (d, J=2.8 Hz, 1H), 8.18 (s, 1H), 8.10 (d, J=9.2 Hz, 1H), 7.79 (s, 1H), 7.38 (d, J=2.8 Hz, 1H), 7.23 (dd, J=2.0, 8.8 Hz, 1H), 6.53-6.52 (m, 1H), 3.98 (s, 3H); MS: MS m/z 260.0 (M++1).
  • 15
  • [ 55934-22-0 ]
  • [ 153624-46-5 ]
  • [ 1409964-05-1 ]
YieldReaction ConditionsOperation in experiment
85% In 1,4-dioxane; water Preparation of 4-chloro-2-(4-isopropoxyphenyl)-7-methoxyquinoline Preparation of 4-chloro-2-(4-isopropoxyphenyl)-7-methoxyquinoline To a degassed solution of 2,4-dichloro-7-methoxyquinoline (1 g, 4.3 mmol) in dioxane/water (8:2) was added 4-isopropoxyphenylboronic acid (870 mg, 4.82 mmol) followed by potassium carbonate (1.2 g, 8.7 mmol) and Pd(PPh3)4 (253 mg, 0.22 mmol) at room temperature under nitrogen atmosphere. The reaction mass was heated at 90° C. for 18 h. The solvent was removed under reduced pressure and the residue was diluted with water and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulphate and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography to afford 4-chloro-2-(4-isopropoxyphenyl)-7-methoxyquinoline (1.2 g, 85%) as off white solid. MS: MS m/z 328.7 (M++1).
85% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 90℃; for 18h; Inert atmosphere; Preparation of 4-chloro-2-(4-isopropoxyphenyl)-7-methoxyquinoline To a degassed solution of 2,4-dichloro-7-methoxyquinoline (1 g, 4.3 mmol) in dioxane/water (8:2) was added 4-isopropoxyphenylboronic acid (870 mg, 4.82 mmol) followed by potassium carbonate (1.2 g, 8.7 mmol) and Pd(PPh3)4(253 mg, 0.22 mmol) at room temperature under nitrogen atmosphere. The reaction mass was heated at 90° C. for 18 h. The solvent was removed under reduced pressure and the residue was diluted with water and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulphate and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography to afford 4-chloro-2-(4-isopropoxyphenyl)-7-methoxyquinoline (1.2 g, 85%) as off white solid. MS: MS m/z 328.7 (M++1)
  • 16
  • [ 27037-34-9 ]
  • [ 855765-21-8 ]
  • [ 55934-21-9 ]
  • [ 55934-22-0 ]
YieldReaction ConditionsOperation in experiment
39% In ethyl acetate; trichlorophosphate; Step 2: Preparation of 2,4-dichloro-5-methoxyquinoline and 2,4-dichloro-7-methoxyquinoline A solution of 4-hydroxy-5-methoxyquinoline-2(1H)-one and <strong>[27037-34-9]4-hydroxy-7-methoxyquinoline-2(1H)-one</strong> (3 g, 15.70 mmol) in POCl3 (3.66 ml, 39.2 mmol) was refluxed for 3 h. The solvent was evaporated under reduced pressure and the residue was diluted with cold water. The aqueous solution was basified by solid sodium carbonate and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography (20percent ethyl acetate in pet ether) to afford mixture of regioisomers. This mixture of regioisomers was separated by SFC purification to afford 2,4-dichloro-5-methoxyquinoline (0.7 g, 39percent) and 2,4-dichloro-7-methoxyquinoline (required isomer) (1.3 g, 72.6percent) as white solid. 2,4-dichloro-7-methoxyquinoline: 1H NMR (400 MHz, CDCl3): delta ppm 8.07-8.04 (d, J=12 Hz, 1H), 7.35-7.34 (m, 2H), 7.28-7.26 (m, 1H), 3.94 (s, 3H);
  • 17
  • [ 55934-22-0 ]
  • 4-chloro-7-methoxyquinolin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With methanesulfonic acid In butan-1-ol at 110℃;
  • 18
  • [ 55934-22-0 ]
  • 7-methoxy-2-oxo-1,2-dihydroquinoline-4-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: methanesulfonic acid / butan-1-ol / 110 °C 2: sodium 4-methylbenzenesulfinate / N,N-dimethyl-formamide / 46 h / 140 °C
  • 19
  • [ 55934-22-0 ]
  • 7-methoxy-2-(4-methyl-1,4-diazepan-1-yl)-N-(1-methylpiperidin-4-yl)quinolin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 4 h / 150 °C 2: trifluoroacetic acid / isopropyl alcohol / 0.33 h / 160 °C / Microwave irradiation
  • 20
  • [ 41838-46-4 ]
  • [ 55934-22-0 ]
  • C16H20ClN3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 150℃; for 4h;
  • 21
  • [ 55934-22-0 ]
  • 2,4-difluoro-7-methoxyquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With cesium fluoride In dimethyl sulfoxide at 140℃; for 2h; 1 10184] To a round-bottom flask equipped with a stir bar was added 2,4-dichioro-7-methoxyquinoline (905 mg, 3.97 mmol), CsF (1.51 g, 9.92 mmol) and DMSO (20 mE). The mixture was stirred at 140° C. for 2 h. The mixture was allowed to cool to room temperature; then was transferred toseparatory thnnel and diluted with watet The mixture was extracted with EtOAc. The organic phase was dried over Mg504 filtered; then concentrated in vacuo to afford 2,4- difluoro-7-methoxyquinoline as a light-orange solid (706 mg, 91%). MS: MS mlz 196.2 (MTh-1).
  • 22
  • [ 55934-22-0 ]
  • 4-fluoro-2,7-dimethoxyquinoline [ No CAS ]
  • 2-fluoro-4,7-dimethoxyquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: cesium fluoride / dimethyl sulfoxide / 2 h / 140 °C 2: tetrahydrofuran; methanol / 16 h / 20 °C
  • 23
  • [ 55934-22-0 ]
  • tert-butyl (2R,6S,7R,13aS,14aR,16aS,Z)-14a-(1-(fluoromethyl)cyclopropylsulfonylcarbamoyl)-2-(2-(4-isopropoxyphenyl)-7-methoxyquinolin-4-yloxy)-7,9-dimethyl-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-ylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; 1,4-dioxane / 18 h / 90 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / tetrahydrofuran; dimethyl sulfoxide / 2 h / 20 °C / Inert atmosphere
  • 24
  • [ 55934-22-0 ]
  • (2R,6S,7R,9R,13aS,14aR,16aS,Z)-6-amino-N-(1-(fluoromethyl)cyclopropylsulfonyl)-2-(2-(4-isopropoxyphenyl)-7-methoxyquinolin-4-yloxy)-7,9-dimethyl-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxamide hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; 1,4-dioxane / 18 h / 90 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / tetrahydrofuran; dimethyl sulfoxide / 2 h / 20 °C / Inert atmosphere 3: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C
  • 25
  • [ 55934-22-0 ]
  • 1,1,1-trifluoro-2-methylpropan-2-yl ((2R,6S,7R,9R,13aS,14aR,16aS,Z)-14a-(((1-(fluoromethyl)cyclopropyl)sulfonyl)carbamoyl)-2-((2-(4-isopropoxyphenyl)-7-methoxyquinolin-4-yl)oxy)-7,9-dimethyl-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; 1,4-dioxane / 18 h / 90 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / tetrahydrofuran; dimethyl sulfoxide / 2 h / 20 °C / Inert atmosphere 3: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C 4: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 20 °C
  • 26
  • [ 110-91-8 ]
  • [ 55934-22-0 ]
  • 4-(4-chloro-7-methoxyquinoline-2-yl)morpholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
49.1% With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 140℃; for 18h; Preparation of 4-(4-Chloro-7-methoxy quinoline-2-yl) morpholine To a solution of 2,4-dichloro-7-methoxyquinoline (1 g, 4.38 mmol) in 1,4-dioxane (15 ml) was added morpholine (1.9 g, 4.38 mmol) followed by DIPEA (1.7 g, 13.15 mmol) at room temperature. The reaction mass was heated at 140° C. for 18 h. The reaction mass was diluted with water and extracted with ethyl acetate. The combined organic layer was dried over anhydrous Na2SO4and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography to get desired compound (0.6 g, 49.1%) as white solid.1H NMR (400 MHz, CDCl3): δ ppm 7.89-7.86 (d, J=12 Hz, 1H), 7.07 (s, 1H), 6.97-6.94 (d, J=12 Hz, 1H), 6.89 (s, 1H), 3.91 (s, 3H), 3.85-3.82 (m, 4H), 3.69-3.66 (m, 4H); MS: MS m/z 279.1 (M++1).
  • 27
  • [ 55934-22-0 ]
  • [ 480438-54-8 ]
  • 4-chloro-2-(3-fluoro-4-isopropoxyphenyl)-7-methoxyquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 90℃; for 18h; Sealed tube; 1 Preparation of 4-chloro-2-(3-fluoro-4-isopropoxyphenyl)-7-methoxyisoquinoline To a solution of 2,4-dichloro-7-methoxyisoquinolin (0.25 g, 1.1 mmol), 3-Fluoro-4-isopropoxyphenylboronic acid (0.21 g, 1.1 mmol) in 1,4-Dioxane (5 ml) and water (1 ml) was added K2CO3(0.3 g, 2.2 mmol). The reaction mass was degasified for 20 min. Pd (Ph3P)4(0.06 g, 0.05 mmol) was added to the above reaction mass and degasified again for 5 min at room temperature. The reaction vessel (Pressure tube) was sealed and heated at 90° C. for 18 h. The reaction mass was evaporated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography to get desired compound (0.2 g, 54%) as white solid.1H NMR (400 MHz, CHLOROFORM-d): δ ppm 8.08 (d, J=9.26 Hz, 1H) 7.93 (dd, J=12.51, 2.25 Hz, 1H) 7.80 (dt, J=8.50, 1.00 Hz, 1H) 7.74 (s, 1H) 7.45 (d, J=2.50 Hz, 1H) 7.09 (t, J=8.50 Hz, 1H), 3.99 (s, 3H), 3.95 (m, 1H), 1.41 (d, J=6.25 Hz, 6H).
  • 28
  • [ 123-75-1 ]
  • [ 55934-22-0 ]
  • 4-chloro-7-methoxy-2-(pyrrolidin-1-yl)quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
43.4% With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 140℃; for 18h; Preparation of 4-Chloro-7-methoxy-2-(pyrrolidin-1-yl) quinoline To a solution of 2,4-dichloro-7-methoxyquinoline (0.1 g, 0.43 mmol) in 1,4-Dioxane (10 ml) was added pyrrolidine (0.3 g, 0.43 mmol) followed by DIPEA (0.11 g, 0.87 mmol) at room temperature. The reaction mass was heated at 140° C. for 18 h. The reaction mass was diluted with water and extracted with ethyl acetate. The combined organic layer was dried over anhydrous Na2SO4and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography to get desired compound (50 mg, 43.4%) as white solid.1H NMR (400 MHz, CDCl3): δ ppm 7.86-7.83 (d, J=12 Hz, 1H), 7.06 (s, 1H), 6.88-6.85 (d, J=12 Hz, 1H), 6.67 (s, 1H), 3.91 (s, 3H), 3.58 (t, J=8 Hz, 4H), 2.03 (t, J=6 Hz, 1H); MS: MS m/z 263.1 (M++1).
  • 29
  • [ 55934-22-0 ]
  • [ 49633-25-2 ]
  • [ 1608477-31-1 ]
YieldReaction ConditionsOperation in experiment
14% With caesium carbonate; In N,N-dimethyl-formamide; at 80℃; for 18h; To a solution of 2,4-dichloro-7-methoxyisoquinolin (0.54 g, 2.36 mmol) in DMF (5 ml) was added Cs2CO3 (1.54 g, 4.74 mmol) followed by <strong>[49633-25-2]3-isopropyl-1H-pyrazole</strong> (0.78 g, 7.10 mmol). The reaction mixture was heated to 80 C. for 18 h. The reaction mass was concentrated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4 and then concentrated under reduced pressure to get crude compound. The crude compound was silica gel chromatography to get desired compound (0.1 g, 14%) as white solid. 1H NMR (400 MHz, CDCl3): delta ppm 8.60 (d, J=2.51 Hz, 1H) 8.07 (d, J=9.04 Hz, 1H) 8.15 (s, 1H) 8.07 (d, J=9.04 Hz, 1H) 8.15 (s, 1H) 7.26 (s, 2H) 7.16-7.22 (m, 1H) 6.35 (d, J=2.51 Hz, 1H) 3.97-3.99 (m, 4H) 3.10 (quin, J=7.03 Hz, 1H) 1.36 (s, 4H) 1.34 (s, 3H). MS: MS m/z 302.1 (M++1).
  • 30
  • [ 288-32-4 ]
  • [ 55934-22-0 ]
  • 4-chloro-2-(1H-imidazol-1-yl)-7-methoxyquinoline [ No CAS ]
  • 2-chloro-4-(1H-imidazol-1-yl)-7-methoxyquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 18h; 1 Step 1: 4-chloro-2-(1 H-imidazol- 1 -yl)-7-methoxy- quinoline and 2-chloro-4-(1H-imidazol-1 -yl)-7-methoxyquinoline To a solution of 2,4-dichloro-7-methoxyisoquinolin (0.5 g, 2.19 mmol) in DMF (5 ml) was added Cs2CO3 (1.54 g, 4.74 mmol) followed by imidazole (0.16 g, 2.41 mmol). The reaction mixture was heated to 80° C. for 18 h. The reaction mass was concentrated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography to get a mixture of 4-chloro-2-(1H-imida- zol-1 -yl)-7-methoxyquinoline and 2-chloro-4-(1 H-imidazol-1-yl)-7-methoxyquinoline. MS: MS mlz 260.1 (M+2).
  • 31
  • [ 55934-22-0 ]
  • [ 20154-03-4 ]
  • [ 1608477-08-2 ]
YieldReaction ConditionsOperation in experiment
54% With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 18h; 1 Step 1:Preparation of 4-chloro-7-methoxy-2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)quinoline To a solution of 2,4-dichloro-7-methoxyisoquinolin (0.5 g, 2.19 mmol) in DMF (5 ml) was added Cs2CO3 (0.3 g, 2.2 mmol) followed by 3-(trifluoromethyl)-1H-pyrazole (0.9 g, 6.58 mmol). The reaction mixture was heated to 80° C. for 18 h. The reaction mass was evaporated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4; filtered; then evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography to get 4-chloro-7-methoxy-2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)quinoline (0.45 g, 1.37 mmol) 54% as white solid. 1H NMR (400 MHz, CDCl3): δ ppm 8.60 (d, J=2.51 Hz, 1H) 8.07 (d, J=9.04 Hz, 1H) 8.15 (s, 1H) 8.07 (d, J=9.04 Hz, 1H) 8.15 (s, 1H) 7.26 (s, 2H) 7.16-7.22 (m, 1H) 6.35 (d, J=2.51 Hz, 1H) 3.97-3.99 (m, 4H) MS: MS m/z 330.1 (M++1).
  • 32
  • [ 55934-22-0 ]
  • [ 35132-20-8 ]
  • (1R,2R)-N1,N2-bis(4-chloro-7-methoxyquinolin-2-yl)-1,2-diphenylethane-1,2-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 80℃; for 2h; Inert atmosphere;
  • 33
  • [ 55934-22-0 ]
  • (1R,2R)-N1,N2-bis(7-methoxy-4-(pyrrolidin-1-yl)quinolin-2-yl)-1,2-diphenylethane-1,2-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: bis(dibenzylideneacetone)-palladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate / toluene / 2 h / 80 °C / Inert atmosphere 2: 0.5 h / 190 °C / Sealed tube
  • 34
  • [ 55934-22-0 ]
  • C42H44N6O2*C2HF6NO4S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: bis(dibenzylideneacetone)-palladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate / toluene / 2 h / 80 °C / Inert atmosphere 2: 0.5 h / 190 °C / Sealed tube 3: dichloromethane / 0.5 h / 0 °C
  • 35
  • [ 55934-22-0 ]
  • C36H49N5O*4C2H2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 24 h / Reflux; Inert atmosphere; Alkaline conditions 2: ethanol / 5 h / Reflux 3: sodium tetrahydroborate; methanol / 2 h / 0 °C / Reflux 4: isopropyl alcohol / 0.5 h / Reflux
  • 36
  • [ 55934-22-0 ]
  • C34H45N5O*4C2H2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 24 h / Reflux; Inert atmosphere; Alkaline conditions 2: ethanol / 5 h / Reflux 3: sodium tetrahydroborate; methanol / 2 h / 0 °C / Reflux 4: isopropyl alcohol / 0.5 h / Reflux
  • 37
  • [ 55934-22-0 ]
  • C42H59N7O*6C2H2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 24 h / Reflux; Inert atmosphere; Alkaline conditions 2: ethanol / 5 h / Reflux 3: sodium tetrahydroborate; methanol / 2 h / 0 °C / Reflux 4: isopropyl alcohol / 0.5 h / Reflux
  • 38
  • [ 55934-22-0 ]
  • C40H55N7O*6C2H2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 24 h / Reflux; Inert atmosphere; Alkaline conditions 2: ethanol / 5 h / Reflux 3: sodium tetrahydroborate; methanol / 2 h / 0 °C / Reflux 4: isopropyl alcohol / 0.5 h / Reflux
  • 43
  • [ 55934-22-0 ]
  • 7-methoxy-2,4-bis{4-[(4-dimethylaminobutyl)aminomethyl]phenyl}quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 24 h / Reflux; Inert atmosphere; Alkaline conditions 2: ethanol / 5 h / Reflux 3: sodium tetrahydroborate; methanol / 2 h / 0 °C / Reflux
  • 44
  • [ 55934-22-0 ]
  • 7-methoxy-2,4-bis{4-[(3-dimethylaminopropyl)aminomethyl]phenyl}quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 24 h / Reflux; Inert atmosphere; Alkaline conditions 2: ethanol / 5 h / Reflux 3: sodium tetrahydroborate; methanol / 2 h / 0 °C / Reflux
  • 45
  • [ 55934-22-0 ]
  • 7-methoxy-2,4-bis{4-[(4-(4-methylpiperazin-1-yl)butyl)aminomethyl]phenyl}quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 24 h / Reflux; Inert atmosphere; Alkaline conditions 2: ethanol / 5 h / Reflux 3: sodium tetrahydroborate; methanol / 2 h / 0 °C / Reflux
  • 46
  • [ 55934-22-0 ]
  • 7-methoxy-2,4-bis{4-[(3-(4-methylpiperazin-1-yl)propyl)aminomethyl]phenyl}quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 24 h / Reflux; Inert atmosphere; Alkaline conditions 2: ethanol / 5 h / Reflux 3: sodium tetrahydroborate; methanol / 2 h / 0 °C / Reflux
  • 48
  • [ 55934-22-0 ]
  • [ 104-86-9 ]
  • 2-(4-chlorobenzylamino)-4-chloro-7-methoxyquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% With palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In tetrahydrofuran for 3h; Inert atmosphere; Reflux; 8.1 8.1 Synthesis of 2-(4-chlorobenzylamino)-4-chloro-7-methoxyquinoline (8-1) To a solution under nitrogen gas of 2,4-dichloro-7-methoxyquinoline (3.0 g, 13.21 mmol) in dry THF (30 ml) was added 4-chlorobenzylamine (2.79 g, 19.82 mmol) and t-BuONa (2.53 g, 26.42 mmol). The resulting mixture was degassed 5 min with nitrogen, then Xantphos (764 mg, 1.32 mmol) and Pd(OAc)2 (148 mg, 0.66 mmol) were added and the reaction mixture was heated for 3 hours under reflux. The reaction mixture was then cooled to room temperature and concentrated under reduced pressure. The residue was partitioned between brine and EtOAc and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to give a brown solid. The crude product was purified by flash chromatography (gradient Petroleum ether/EtOAC from 9/1 to 6/4) to give 1.5 g (yield 34%) of an off-white solid corresponding to 2-(4-chlorobenzylamino)-4-chloro-7-methoxyquinoline (8-1). HPLC-MS, Method B: tr = 1.86 min, (ES+) C17H14Cl2N2O required 332; found 333 [M+H] 1H NMR (300 MHz, DMSO-d6)
  • 49
  • [ 55934-22-0 ]
  • 2-(4-chlorobenzylamino)-4-(4-tert-butylaminopiperidin-1-yl)-7-methoxyquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium diacetate; sodium t-butanolate / tetrahydrofuran / 3 h / Inert atmosphere; Reflux 2: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 72 h / 140 °C / Sealed tube
  • 50
  • [ 55934-22-0 ]
  • 2-(4-chlorobenzylamino)-4-(4-tert-butylaminopiperidin-1-yl)-7-hydroxyquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium diacetate; sodium t-butanolate / tetrahydrofuran / 3 h / Inert atmosphere; Reflux 2: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 72 h / 140 °C / Sealed tube 3: boron tribromide / dichloromethane / 48 h / 0 - 20 °C
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