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[ CAS No. 897016-97-6 ]

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Chemical Structure| 897016-97-6
Chemical Structure| 897016-97-6
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CAS No. :897016-97-6 MDL No. :MFCD18434461
Formula : C17H25BFNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :321.19 g/mol Pubchem ID :-
Synonyms :

Safety of [ 897016-97-6 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 897016-97-6 ]

  • Downstream synthetic route of [ 897016-97-6 ]

[ 897016-97-6 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 897016-96-5 ]
  • [ 73183-34-3 ]
  • [ 897016-97-6 ]
YieldReaction ConditionsOperation in experiment
65% With potassium acetate In N,N-dimethyl-formamide at 80℃; for 8h; 1 4-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)morpholine: A 10 mL microwave reaction tube with septum closure was charged with 4-(4-bromo-3-fluorobenzyl)morpholine (405 mg, 1.48 mmol),Bis(pinacolato)diboron (516 mg, 2.03 mmol), Pd(dppf)Cl2.CH2Cl2 (62 mg, 0.076 mmol), potassium acetate (659 mg, 6.72 mmol), and DMF (3.6 mL). The vial was placed under nitrogen by evacuation/backfilling (5 cycles) and stirred at 80° C. for 8 hours. The reaction was cooled, diluted with ethyl acetate (25 mL) and filtered. The organics were washed with water (25 mL) and saturated sodium chloride (25 mL). The organic layer was then dried over MgSO4 and concentrated to a dark oil. The product was purified by silica gel chromatography eluting with 2% MeOH in CHCl3 to give 310 mg (65%) of an off-white solid.
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 120℃; for 0.5h; Microwave irradiation; 7 To a solution of 4-(4-bromo-3-fluorobenzyl)morpholine (preparation 12) (445 mg, 1.62 mmol) in 1,4-dioxane (4 ml), bis(pinacolato)diboron (495 mg, 1.95 mmol), potassiumacetate (350 mg, 3.57 mmol) and [1,1’-Bis(diphenylphosphino)ferrocene]dichloropalladium(ll) (59 mg, 0.081 mmol) were added and the mixture was heated under microwave irradiation at 120 °C for 30 minutes. The reaction mixture was concentrated in vacuo, diluted with dichloromethane (10 ml), washed with water (5 ml) and filtered through a phase separator. The filtrate was concentrated in vacuo to afford the boronic ester intermediate as determined by 1H NMR in CDCl3. The crude boronic ester was then dissolved in DMF (10 ml) and 2-chloro-6- fluoro-N-(2-(pyrrolidin-1-yl)ethyl)quinoline-4-carboxamide (preparation 4) (261 mg, 0.81mmol), potassium phosphate tribasic (344 mg, 1.62 mmol) in water (2 ml), bis(triphenylphosphine) palladium(ll) dichloride (71 mg, 0.062 mmol) were added. The reaction mixture was heated under microwave irradiation for 30 minutes at 12000. The reaction crude was filtered through a CeliteTM pad and washed with ethyl acetate (4 x 10 ml). The combined organic phases were washed with 5% lithium chloride aqueoussolution (3 x 10 ml), brine (10 ml), dried over magnesium sulphate and concentrated in vacuo. The mixture was purified by mass directed autoprep HPLC to afford the desired product as an off-white solid (193mg, 0.4Ommol, 25% yield over 2 steps). 1H NMR (500 MHz; CDCl3) δ 1.93 (brs, 4H), 2.49 (t, 4H, J = 4.4 Hz), 2.59 (brs, 4H), 2.78 (brs, 2H), 3.56 (5, 2H), 3.74 (t, 4H, J = 4.7 Hz), 3.78 (brs, 2H), 7.23-7.30 (m, 2H), 7.53 (ddd, 1H, J= 2.8 Hz, J= 8.1 Hz, J= 9.3 Hz), 8.02-8.08 (m, 3H), 8.19 (dd, 1H, J= 5.5 Hz, J= 9.3 Hz) ppm. Purity by LCMS (UV Chromatogram, 190-450 nm) 95 %, rt = 0.68 min m/z 481 (M+H)+
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 120℃; for 0.5h; Microwave irradiation; 7 6-fluoro-2-(2-fluoro-4-(morpholinomethyl)phenyl)-N-(2-(pyrrolidin-1-yl)ethyl)quinoline-4-carboxamide Example 7 6-fluoro-2-(2-fluoro-4-(morpholinomethyl)phenyl)-N-(2-(pyrrolidin-1-yl)ethyl)quinoline-4-carboxamide To a solution of 4-(4-bromo-3-fluorobenzyl)morpholine (preparation 12) (445 mg, 1.62 mmol) in 1,4-dioxane (4 ml), bis(pinacolato)diboron (495 mg, 1.95 mmol), potassium acetate (350 mg, 3.57 mmol) and [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (59 mg, 0.081 mmol) were added and the mixture was heated under microwave irradiation at 120° C. for 30 minutes. The reaction mixture was concentrated in vacuo, diluted with dichloromethane (10 ml), washed with water (5 ml) and filtered through a phase separator. The filtrate was concentrated in vacuo to afford the boronic ester intermediate as determined by 1H NMR in CDCl3. The crude boronic ester was then dissolved in DMF (10 ml) and 2-chloro-6-fluoro-N-(2-(pyrrolidin-1-yl)ethyl)quinoline-4-carboxamide (preparation 4) (261 mg, 0.81 mmol), potassium phosphate tribasic (344 mg, 1.62 mmol) in water (2 ml), bis(triphenylphosphine) palladium(II) dichloride (71 mg, 0.062 mmol) were added. The reaction mixture was heated under microwave irradiation for 30 minutes at 120° C. The reaction crude was filtered through a Celite pad and washed with ethyl acetate (4*10 ml). The combined organic phases were washed with 5% lithium chloride aqueous solution (3*10 ml), brine (10 ml), dried over magnesium sulphate and concentrated in vacuo. The mixture was purified by mass directed autoprep HPLC to afford the desired product as an off-white solid (193 mg, 0.40 mmol, 25% yield over 2 steps). 1H NMR (500 MHz; CDCl3) δ 1.93 (brs, 4H), 2.49 (t, 4H, J=4.4 Hz), 2.59 (brs, 4H), 2.78 (brs, 2H), 3.56 (s, 2H), 3.74 (t, 4H, J=4.7 Hz), 3.78 (brs, 2H), 7.23-7.30 (m, 2H), 7.53 (ddd, 1H, J=2.8 Hz, J=8.1 Hz, J=9.3 Hz), 8.02-8.08 (m, 3H), 8.19 (dd, 1H, J=5.5 Hz, J=9.3 Hz) ppm. Purity by LCMS (UV Chromatogram, 190-450 nm) 95%, rt=0.68 min, m/z 481 (M+H)+
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 120℃; for 0.005h; Microwave irradiation;

  • 2
  • 2-(5-bromopyridin-2-yl)-N-(3-fluorobenzyl)acetamide [ No CAS ]
  • [ 897016-97-6 ]
  • KX2-393 [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With potassium carbonate In ethanol; water at 150℃; for 0.166667h; Microwave irradiation; 1 Synthesis of Compound 136, KX2-393: A 10 mL microwave reaction tube with septum closure was charged with 4-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)morpholine (307 mg, 0.96 mmol), 2-(5-bromopyridin-2-yl)-N-(3-fluorobenzyl)acetamide (247 mg, 0.77 mmol), and FibreCat 1007 (60 mg, 0.03 mmol). Ethanol (3 mL) was added followed by aqueous potassium carbonate solution (1.2 mL, 1.0 M, 1.2 mmol). The tube was sealed and heated under microwave conditions at 150° C. for 10 minutes. The reaction was cooled and concentrated to remove the majority of the ethanol, and then taken up in 10 mL of ethyl acetate and washed successively with water and saturated sodium chloride solution. The organic layer was dried with MgSO4, filtered, and concentrated. The material was purified by column chromatography (silica gel, 100:0 CHCl3/MeOH to 95:5 CHCl3/MeOH) to provide ALB 30351 as a white solid (240 mg, 74%): mp 91-92° C.; 1H NMR (300 MHz,CDCl3) δ 8.71 (br s, 1H), 7.86-7.84 (m, 1H), 7.78 (br s, 1 H), 7.37 (t, 2H, J=7.5 Hz), 7.28-7.21 (m, 3H), 7.02 (dd, 1H, J=0.6 Hz, J=7.7 Hz), 6.98-6.90 (m, 2H), 4.49 (d, 2H, J=5.9 Hz), 3.84 (s, 2H), 372-3.75 (m, 4H), 3.52 (s, 2H), 2.47-2.50 (m, 4H); HPLC (Method A) 98.7% (AUC), tR=3.866 min.; APCI MS m/z 438 [M+H]+.
  • 3
  • 2-(5-bromopyridin-2-yl)-N-(3-fluorobenzyl)acetamide [ No CAS ]
  • [ 897016-97-6 ]
  • KX2-392 [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With potassium carbonate In ethanol; water at 150℃; for 0.166667h; Microwave irradiation; 1 Synthesis of Compound 133, KX2-392: A 10 mL microwave reaction tube with septum closure was charged with 4-(2-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethyl)morpholine (175 mg, 0.50 mmol), 2-(5-bromopyridin-2-yl)-N-(3-fluorobenzyl)acetamide (121 mg, 0.37 mmol), and FibreCat 1007 (30 mg, 0.03 mmol). Ethanol (3 mL) was added followed by aqueous potassium carbonate solution (0.600 mL, 1.0 M, 0.60 mmol). The tube was sealed and heated under microwave conditions at 150° C. for 10 minutes. The reaction was cooled, filtered, and concentrated to remove the majority of the ethanol. The residue was then taken up in 10 mL of ethyl acetate and washed successively with water and saturated sodium chloride solution. The organic layer was dried with MgSO4, filtered, and concentrated. The material was purified by column chromatography (silica gel, 100:0 CHCl3/MeOH to 95:5 CHCl3/MeOH) to provide ALB 30350 as a white solid (70 mg, 40%): mp 126-127° C.; 1H NMR (500 MHz,CDCl3) δ 8.67 (br s, 1H), 7.77-7.85 (m, 2H), 7.21-7.37 (m, 3H), 7.02 (d, 1H, J=7.7 Hz), 6.90-6.97 (m, 2H), 6.82 (dd, 1H, J=2.5 Hz, J=8.6 Hz), 6.76 (dd, 1H, J=2.4 Hz, J=12.4 Hz), 4.49 (d, 2H, J=5.9 Hz), 4.15 (t, 2H, J=5.7 Hz), 3.83 (s, 2H), 3.71-3.78 (m, 4H), 2.83 (t, 2H, J=5.7 Hz), 2.56-2.63 (m, 4H); HPLC (Method A) >99% (AUC), tR=4.026 min.; APCI MS m/z 468 [M+H]+.
  • 4
  • [ 897016-97-6 ]
  • 2-chloro-6-fluoro-N-(2-pyrrolidin-1-ylethyl)quinoline-4-carboxamide [ No CAS ]
  • 6-fluoro-2-(2-fluoro-4-(morpholinomethyl)phenyl)-N-(2-(pyrrolidin-1-yl)ethyl)quinoline-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
193 mg With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate In water; N,N-dimethyl-formamide at 120℃; for 0.5h; Microwave irradiation; 7 6-fluoro-2-(2-fluoro-4-(morpholinomethyl)phenyl)-N-(2-(pyrrolidin-1-yl)ethyl)quinoline-4-carboxamide To a solution of 4-(4-bromo-3-fluorobenzyl)morpholine (preparation 12) (445 mg, 1.62 mmol) in 1,4-dioxane (4 ml), bis(pinacolato)diboron (495 mg, 1.95 mmol), potassiumacetate (350 mg, 3.57 mmol) and [1,1’-Bis(diphenylphosphino)ferrocene]dichloropalladium(ll) (59 mg, 0.081 mmol) were added and the mixture was heated under microwave irradiation at 120 °C for 30 minutes. The reaction mixture was concentrated in vacuo, diluted with dichloromethane (10 ml), washed with water (5 ml) and filtered through a phase separator. The filtrate was concentrated in vacuo to afford the boronic ester intermediate as determined by 1H NMR in CDCl3. The crude boronic ester was then dissolved in DMF (10 ml) and 2-chloro-6- fluoro-N-(2-(pyrrolidin-1-yl)ethyl)quinoline-4-carboxamide (preparation 4) (261 mg, 0.81mmol), potassium phosphate tribasic (344 mg, 1.62 mmol) in water (2 ml), bis(triphenylphosphine) palladium(ll) dichloride (71 mg, 0.062 mmol) were added. The reaction mixture was heated under microwave irradiation for 30 minutes at 12000. The reaction crude was filtered through a CeliteTM pad and washed with ethyl acetate (4 x 10 ml). The combined organic phases were washed with 5% lithium chloride aqueoussolution (3 x 10 ml), brine (10 ml), dried over magnesium sulphate and concentrated in vacuo. The mixture was purified by mass directed autoprep HPLC to afford the desired product as an off-white solid (193mg, 0.4Ommol, 25% yield over 2 steps). 1H NMR (500 MHz; CDCl3) δ 1.93 (brs, 4H), 2.49 (t, 4H, J = 4.4 Hz), 2.59 (brs, 4H), 2.78 (brs, 2H), 3.56 (5, 2H), 3.74 (t, 4H, J = 4.7 Hz), 3.78 (brs, 2H), 7.23-7.30 (m, 2H), 7.53 (ddd, 1H, J= 2.8 Hz, J= 8.1 Hz, J= 9.3 Hz), 8.02-8.08 (m, 3H), 8.19 (dd, 1H, J= 5.5 Hz, J= 9.3 Hz) ppm. Purity by LCMS (UV Chromatogram, 190-450 nm) 95 %, rt = 0.68 min m/z 481 (M+H)+
193 mg With potassium phosphate; bis(triphenylphosphine)palladium(II) dichloride In water; N,N-dimethyl-formamide at 120℃; for 0.5h; Microwave irradiation; 7 6-fluoro-2-(2-fluoro-4-(morpholinomethyl)phenyl)-N-(2-(pyrrolidin-1-yl)ethyl)quinoline-4-carboxamide Example 7 6-fluoro-2-(2-fluoro-4-(morpholinomethyl)phenyl)-N-(2-(pyrrolidin-1-yl)ethyl)quinoline-4-carboxamide To a solution of 4-(4-bromo-3-fluorobenzyl)morpholine (preparation 12) (445 mg, 1.62 mmol) in 1,4-dioxane (4 ml), bis(pinacolato)diboron (495 mg, 1.95 mmol), potassium acetate (350 mg, 3.57 mmol) and [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (59 mg, 0.081 mmol) were added and the mixture was heated under microwave irradiation at 120° C. for 30 minutes. The reaction mixture was concentrated in vacuo, diluted with dichloromethane (10 ml), washed with water (5 ml) and filtered through a phase separator. The filtrate was concentrated in vacuo to afford the boronic ester intermediate as determined by 1H NMR in CDCl3. The crude boronic ester was then dissolved in DMF (10 ml) and 2-chloro-6-fluoro-N-(2-(pyrrolidin-1-yl)ethyl)quinoline-4-carboxamide (preparation 4) (261 mg, 0.81 mmol), potassium phosphate tribasic (344 mg, 1.62 mmol) in water (2 ml), bis(triphenylphosphine) palladium(II) dichloride (71 mg, 0.062 mmol) were added. The reaction mixture was heated under microwave irradiation for 30 minutes at 120° C. The reaction crude was filtered through a Celite pad and washed with ethyl acetate (4*10 ml). The combined organic phases were washed with 5% lithium chloride aqueous solution (3*10 ml), brine (10 ml), dried over magnesium sulphate and concentrated in vacuo. The mixture was purified by mass directed autoprep HPLC to afford the desired product as an off-white solid (193 mg, 0.40 mmol, 25% yield over 2 steps). 1H NMR (500 MHz; CDCl3) δ 1.93 (brs, 4H), 2.49 (t, 4H, J=4.4 Hz), 2.59 (brs, 4H), 2.78 (brs, 2H), 3.56 (s, 2H), 3.74 (t, 4H, J=4.7 Hz), 3.78 (brs, 2H), 7.23-7.30 (m, 2H), 7.53 (ddd, 1H, J=2.8 Hz, J=8.1 Hz, J=9.3 Hz), 8.02-8.08 (m, 3H), 8.19 (dd, 1H, J=5.5 Hz, J=9.3 Hz) ppm. Purity by LCMS (UV Chromatogram, 190-450 nm) 95%, rt=0.68 min, m/z 481 (M+H)+
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In water; N,N-dimethyl-formamide at 120℃; for 0.5h; Microwave irradiation;
  • 5
  • [ 133059-43-5 ]
  • [ 897016-97-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: chloroform / 1 h / 58 - 60 °C / Sealed tube 1.2: 12 h / 58 - 60 °C / Sealed tube 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 0.5 h / 120 °C / Microwave irradiation
Multi-step reaction with 2 steps 1.1: chloroform / 1 h / 58 - 60 °C / Sealed tube 1.2: 12 h / 58 - 60 °C / Sealed tube 2.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 0.5 h / 120 °C / Microwave irradiation
Multi-step reaction with 2 steps 1.1: chloroform / 1 h / 58 - 60 °C / Sealed tube 1.2: 16 h / 58 - 60 °C / Sealed tube 2.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 0.01 h / 120 °C / Microwave irradiation
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