Home Cart 0 Sign in  
X

[ CAS No. 1248399-37-2 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 1248399-37-2
Chemical Structure| 1248399-37-2
Chemical Structure| 1248399-37-2
Structure of 1248399-37-2 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 1248399-37-2 ]

Related Doc. of [ 1248399-37-2 ]

Alternatived Products of [ 1248399-37-2 ]

Product Details of [ 1248399-37-2 ]

CAS No. :1248399-37-2 MDL No. :MFCD14652180
Formula : C10H15BrN2O Boiling Point : -
Linear Structure Formula :- InChI Key :NDZCQLBVBUYBKW-UHFFFAOYSA-N
M.W :259.14 Pubchem ID :53211528
Synonyms :

Safety of [ 1248399-37-2 ]

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 [ 1248399-37-2 ]

* 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 [ 1248399-37-2 ]

[ 1248399-37-2 ] Synthesis Path-Downstream   1~30

  • 1
  • [ 766-11-0 ]
  • [ 3179-63-3 ]
  • [ 1248399-37-2 ]
YieldReaction ConditionsOperation in experiment
100% Stage #1: 3-Dimethylamino-1-propanol With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 2-fluoro-5-bromo-pyridine In tetrahydrofuran at 50℃; for 2h; 3-((5-Bromopyridin-2-yl)oxy)-N,N-dimethylpropan-1-amine (6) Sodium hydride (2.10 g, 53 mmol) was added in portions to an ice-cooled solution of 4.33 g 3-(dimethylamino)prop-1-ol (42 mmol) in 75 ml dry THF. After complete addition the cooling bath was removed and stirring was continued for 30 min at ambient temperature. Subsequently, 6.16 g 2-fluoro-5-bromopyridine (35 mmol) were added to the mixture and the temperature was increased to 50°C for two hours. The reaction was cooled to ambient temperature and quenched by dropwise addition of 70 ml water. The mixture was diluted with EtOAc, transferred to a separatory funnel and the organic phase was washed twice with brine. After drying with Na2SO4, the organic phase was evaporated under reduced pressure to yield 9.18 g (quant.) of the title compound as yellow oil in sufficient purity. 1H NMR (200 MHz, CDCl3) δ 8.15 (dd, J = 2.6, 0.6 Hz, 1H), 7.60 (dd, J = 8.8, 2.6 Hz, 1H), 6.62 (dd, J = 8.8, 0.6 Hz, 1H), 4.28 (t, J = 6.6 Hz, 2H), 2.49 - 2.35 (m, 2H), 2.24 (s, 6H), 2.02 - 1.81 (m, 2H). 13C NMR (50 MHz, CDCl3) δ 162.8, 147.6, 141.1, 112.8, 111.6, 64.8, 56.5, 45.6, 27.3. HPLC tret = 2.34 min.
100% Stage #1: 3-Dimethylamino-1-propanol With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 2-fluoro-5-bromo-pyridine In tetrahydrofuran at 50℃; for 2h; 3-((5-Bromopyridin-2-yl)oxy)-N,N-dimethylpropan-1-amine (6) Sodium hydride (2.10 g, 53 mmol) was added in portions to an ice-cooled solution of 4.33 g 3-(dimethylamino)prop-1-ol (42 mmol) in 75 ml dry THF. After complete addition the cooling bath was removed and stirring was continued for 30 min at ambient temperature. Subsequently, 6.16 g 2-fluoro-5-bromopyridine (35 mmol) were added to the mixture and the temperature was increased to 50°C for two hours. The reaction was cooled to ambient temperature and quenched by dropwise addition of 70 ml water. The mixture was diluted with EtOAc, transferred to a separatory funnel and the organic phase was washed twice with brine. After drying with Na2SO4, the organic phase was evaporated under reduced pressure to yield 9.18 g (quant.) of the title compound as yellow oil in sufficient purity. 1H NMR (200 MHz, CDCl3) δ 8.15 (dd, J = 2.6, 0.6 Hz, 1H), 7.60 (dd, J = 8.8, 2.6 Hz, 1H), 6.62 (dd, J = 8.8, 0.6 Hz, 1H), 4.28 (t, J = 6.6 Hz, 2H), 2.49 - 2.35 (m, 2H), 2.24 (s, 6H), 2.02 - 1.81 (m, 2H). 13C NMR (50 MHz, CDCl3) δ 162.8, 147.6, 141.1, 112.8, 111.6, 64.8, 56.5, 45.6, 27.3. HPLC tret = 2.34 min.
67% Stage #1: 3-Dimethylamino-1-propanol With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: 2-fluoro-5-bromo-pyridine In N,N-dimethyl-formamide at 30℃; for 4h; 1 3-(5-Bromopyridin-2-yl)oxy-N,N-dimethylpropan-l-amine 3-(Dimethylamino)propan-l-ol (3.09g, 29.95mmol) was added to a mixture of sodium hydride (2.4g, 60.00mmol) in DMF (50mL) over a period of 20 min at r.t. 5-Bromo-2- fluoropyridine (5.8 lg, 33.01 mm ol) was added and the resulting solution stirred for 4 h at 30°C. The reaction was then quenched by the addition of a sat. aqueous solution of ammonium chloride and the resulting mixture concentrated under vacuum. The residue was purified by FCC, eluting with DCM/MeOH in Et20 (10: 1) to afford the desired material (5.2g, 67%) as yellow oil. Mass Spectrum: m/z (ES+)[M+H]+ = 259.
67% Stage #1: 3-Dimethylamino-1-propanol With sodium hydride In N,N-dimethyl-formamide at 17 - 30℃; for 0.333333h; Stage #2: 2-fluoro-5-bromo-pyridine at 30℃; for 4h; 1 Intermediate Q: 3-(5-Bromopyridin-2-yl)oxy- V, V-dimethylpropan-l-amine 3-(Dimethylamino)propan-1-ol (3.09 g, 29.95 mmol) was added to a mixture of sodium hydride (2.4 g, 60.00 mmol) in DMF (50 mL) over a period of 20 min at ambient temperature. 5-Bromo-2-fluoropyridine (5.81 g, 33.01 mmol) was added and the resulting solution stirred for 4 h at 30°C. The reaction was then quenched by the addition of a saturated aqueous solution of ammonium chloride and the resulting mixture concentrated under vacuum. The residue was purified by FCC, eluting with DCM/MeOH ether (10: 1) to afford the desired material (5.2 g, 67%) as yellow oil. Mass Spectrum: m/z (ES+)[M+H]+ 259.
67% Stage #1: 3-Dimethylamino-1-propanol With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: 2-fluoro-5-bromo-pyridine In N,N-dimethyl-formamide at 30℃; for 4h; 3 -(5 -Bromopyridin-2-yl)oxy-N,N-dimethylpropan- 1-amine 3-(Dimethylamino)propan-1-ol (3.09 g, 29.95 mmol) was added to a mixture of sodium hydride (2.4 g, 60.00 mmol) in DMF (50 mL) over a period of 20 mill at ambient temperature. 5-Bromo-2-fluoropyridine (5.81 g, 33.01 mmol) was added and the resulting solution stirred for 4 hours at 30°C. The reaction was then quenched by the addition of asaturated aqueous solution of ammonium chloride and the resulting mixture concentrated under vacuum. The residue was purified by flash column chromatography on silica, eluting with DCM/MeOH ether (10:1) to afford the desired material (5.2 g, 67%) as yellow oil. Mass Spectrum: mlz (ES+)[M+H]+ = 259
With sodium hydride In tetrahydrofuran at 5 - 50℃; for 2h; Inert atmosphere; 1 Intermediate B2 : 3-(5-Br omopyridin-2-yl)oxy-N,N- dimethylpropan-1-amine Sodium hydride (17.05 g, 426.17 mmol) was added portionwise to 3- (dimethylamino)propan-l-ol (35.2 g, 340.94 mmol) in THF (500 mL) at 5°C and the mixture allowed to warm to ambient temperature. 5-Bromo-2-fluoropyridine (50 g, 284.11 mmol) was added and the solution stirred at 50°C for 2 h. The reaction solution was added carefully to ice-water and the aqueous phase was extracted with DCM (3 x 700 mL). The organic phase was dried over Na2S04, filtered and evaporated to afford the desired material as a yellow oil (73.6 g, 100 %). The material was used without further purification. NMR Spectrum: NMR (300MHz, CDCb) δ 1.92 - 2.01 (2 H, m), 2.28 (6 H, s), 2.45 (2 H, t), 4.33 (2 H, t), 6.67 (1 H, dd), 7.65 (1 H, dd), 8.20 (1 H, d). Mass Spectrum: m/z (ES+)[M+H]+ = 259.
3-((5-Bromopyridin-2-yl)oxy)-N,N-dimethylpropan-1-amine (6): 3-((5-Bromopyridin-2-yl)oxy)-N,N-dimethylpropan-1-amine (6): Sodium hydride (2.10 g, 53 mmol) was added in portions to an ice-cooled solution of 4.33 g 3-(dimethylamino)prop-1-ol (42 mmol) in 75 ml dry THF. After complete addition the cooling bath was removed and stirring was continued for 30 min at ambient temperature. Subsequently, 6.16 g 2-fluoro-5-bromopyridine (35 mmol) were added to the mixture and the temperature was increased to 50°C for two hours. The reaction was cooled to ambient temperature and quenched by dropwise addition of 70 ml water. The mixture was diluted with EtOAc, transferred to a separatory funnel and the organic phase was washed twice with brine. After drying with Na2SO4, the organic phase was evaporated under reduced pressure to yield 9.18 g (quant.) of the title compound as yellow oil in sufficient purity. 1H NMR (200 MHz, CDCl3) δ 8.15 (dd, J = 2.6, 0.6 Hz, 1H), 7.60 (dd, J = 8.8, 2.6 Hz, 1H), 6.62 (dd, J = 8.8, 0.6 Hz, 1H), 4.28 (t, J = 6.6 Hz, 2H), 2.49 - 2.35 (m, 2H), 2.24 (s, 6H), 2.02 - 1.81 (m, 2H). 13C NMR (50 MHz, CDCl3) δ 162.8, 147.6, 141.1, 112.8, 111.6, 64.8, 56.5, 45.6, 27.3. HPLC tret = 2.34 min.

  • 2
  • [ 1248399-37-2 ]
  • [ 1821430-35-6 ]
  • [ 1821428-61-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / 4.17 h / -78 - 18 °C / Inert atmosphere 2: chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); caesium carbonate / 1,4-dioxane; water / 2 h / 100 °C
  • 3
  • [ 1248399-37-2 ]
  • [ 1821428-79-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / 4.17 h / -78 - 18 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 1 h / 80 °C / Inert atmosphere; Sealed tube; Microwave irradiation
  • 4
  • [ 1248399-37-2 ]
  • [ 1821428-80-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: n-butyllithium / tetrahydrofuran / 4.17 h / -78 - 18 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 1 h / 80 °C / Inert atmosphere; Sealed tube; Microwave irradiation 3: dichloromethane / 1 h / 20 °C
  • 5
  • [ 1248399-37-2 ]
  • [ 1821430-37-8 ]
  • [ 1821429-10-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / 4.17 h / -78 - 18 °C / Inert atmosphere 2: chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); caesium carbonate / 1,4-dioxane; water / 1 h / 120 °C / Microwave irradiation
  • 6
  • [ 1248399-37-2 ]
  • [ 1821429-17-7 ]
  • [ 1821430-40-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / 4.17 h / -78 - 18 °C / Inert atmosphere 2: chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); caesium carbonate / 1,4-dioxane; water / 1 h / 120 °C / Microwave irradiation
  • 7
  • [ 1248399-37-2 ]
  • [ 1821428-35-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / 4.17 h / -78 - 18 °C / Inert atmosphere 2: chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); potassium carbonate / water; ethanol / 0.5 h / 77 - 80 °C
  • 8
  • [ 1248399-37-2 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / 4.17 h / -78 - 18 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); caesium carbonate / 1,4-dioxane; water / 3 h / 90 °C / Inert atmosphere
  • 9
  • [ 1248399-37-2 ]
  • [ 1821428-37-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / 4.17 h / -78 - 18 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); caesium carbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere
  • 10
  • [ 61676-62-8 ]
  • 3-(5-bromopyridin-2-yl)oxy-N,N-dimethylpropan-1-amine [ No CAS ]
  • [ 918643-56-8 ]
YieldReaction ConditionsOperation in experiment
100% With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; N,N-Dimethyl-3-((5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)oxy)propan-1-amine (7) A solution of 1037 mg (6)(4 mmol) and 781 mg 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.2 mmol) in 16 ml anhydrous THF was cooled to -78°C and 1.68 ml BuLi (4.2 mmol, 2.5 M in hexane) were added dropwise to the stirred solution. After stirring for 30 min at low temperature, TLC indicated full consumption of starting material and the reaction was quenched by addition of 0.5 ml half saturated NH4Cl. The mixture was allowed to warm up to ambient temperature and diluted with EtOAc. The organic phase was washed twice with brine, dried over Na2SO4 and concentrated under reduced pressure. The title compound was obtained as yellow oil (1231 mg, quant. yield). 1H NMR (200 MHz, CDCl3) δ 8.48 (dd, J = 2.0, 0.6 Hz, 1H), 7.87 (dd, J = 8.3, 2.0 Hz, 1H), 6.65 (dd, J = 8.3, 0.6 Hz, 1H), 4.32 (t, J = 6.5 Hz, 2H), 2.46 - 2.35 (m, 2H), 2.21 (s, 6H), 1.99 - 1.83 (m, 2H), 1.29 (s, 12H). 13C NMR (50 MHz, CDCl3) δ 166.0, 154.3, 144.6, 110.3, 83.9, 82.9, 64.4, 56.6, 45.6, 27.4, 24.9. ESI-MS m/z: 329.4 [M+Na]+.
100% With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; N,N-Dimethyl-3-((5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)oxy)propan-1-amine (7) A solution of 1037 mg (6)(4 mmol) and 781 mg 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.2 mmol) in 16 ml anhydrous THF was cooled to -78°C and 1.68 ml BuLi (4.2 mmol, 2.5 M in hexane) were added dropwise to the stirred solution. After stirring for 30 min at low temperature, TLC indicated full consumption of starting material and the reaction was quenched by addition of 0.5 ml half saturated NH4Cl. The mixture was allowed to warm up to ambient temperature and diluted with EtOAc. The organic phase was washed twice with brine, dried over Na2SO4 and concentrated under reduced pressure. The title compound was obtained as yellow oil (1231 mg, quant. yield). 1H NMR (200 MHz, CDCl3) δ 8.48 (dd, J = 2.0, 0.6 Hz, 1H), 7.87 (dd, J = 8.3, 2.0 Hz, 1H), 6.65 (dd, J = 8.3, 0.6 Hz, 1H), 4.32 (t, J = 6.5 Hz, 2H), 2.46 - 2.35 (m, 2H), 2.21 (s, 6H), 1.99 - 1.83 (m, 2H), 1.29 (s, 12H). 13C NMR (50 MHz, CDCl3) δ 166.0, 154.3, 144.6, 110.3, 83.9, 82.9, 64.4, 56.6, 45.6, 27.4, 24.9. ESI-MS m/z: 329.4 [M+Na]+.
11% With n-butyllithium In tetrahydrofuran at -78 - 18℃; for 4.16667h; Inert atmosphere; 1 N,N-Dimethyl-3-[5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridin-2- yl]oxypropan-l-amine Butyllithium (2.5N, 4.8mL, 50.96mmol) was added to a solution of 3-(5-bromopyridin-2- yl)oxy-N,N-dimethylpropan-l -amine (2.07g, 7.99mmol) and 4,4,5, 5-tetramethyl-2- (propan-2-yloxy)-l,3,2-dioxaborolane (2.79g, 15.00mmol) in THF (20mL) at -78°C over 10 minutes under an inert atmosphere. The resulting solution was stirred for 4 h at 18°C. The reaction was then quenched by the addition of a sat. aqueous solution of ammonium chloride then partitioned between EtOAc (lOOmL) and water (lOOmL). The organic layer was concentrated in vacuo and the residue purified by FCC, eluting with EtO Ac/petroleum ether (1 :3) to afford the desired material (270mg, 11%) as a yellow solid. Mass Spectrum: m/z (ES+)[M+H]+ = 225.
11% With n-butyllithium In tetrahydrofuran at -78 - 18℃; for 4.16667h; Inert atmosphere; 1 Intermediate P: V, V-Dimethyl-3-[5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)pyridin-2-yl]oxypropan-l-amine -Butyllithium (2.5N, 4.8 mL, 50.96 mmol) was added to a solution of 3-(5-bromopyridin- 2-yl)oxy-N,N-dimethylpropan-l -amine (Intermediate Q, 2.07 g, 7.99 mmol) and 4,4,5,5- tetramethyl-2-(propan-2-yloxy)-l,3,2-dioxaborolane (2.79 g, 15.00 mmol) in THF (20 mL) at -78°C over 10 minutes under an inert atmosphere. The resulting solution was stirred for 4 h at 18°C. The reaction was then quenched by the addition of a saturated aqueous solution of ammonium chloride then partitioned between EtOAc (100 mL) and water (100 mL). The organic layer was concentrated in vacuo and the residue purified by FCC, eluting with EtO Ac/petroleum ether (1 :3) to afford the desired material (270 mg, 11%) as a yellow solid. Mass Spectrum: m/z (ES+)[M+H]+ = 225
11% With n-butyllithium In tetrahydrofuran at -78 - 18℃; for 4.16667h; Inert atmosphere; N,N-Dimethyl-3-[[5-(4,4,5 ,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)-2-pyridylloxylpropan-1-amine Butyllithium (2.5N, 4.8 mL, 50.96 mmol) was added to a solution of 3-(5-bromopyridin-2-yl)oxy-N,N-dimethylpropan- 1-amine (2.07 g, 7.99 mmol) and 4,4,5,5 -tetramethyl-2-Q,ropan-2-yloxy)-1,3,2-dioxaborolane (2.79 g, 15.00 mmol) in THF (20 mL) at -78°C over10 minutes under an inert atmosphere. The resulting solution was stirred for 4 hour at18°C. The reaction was then quenched by the addition of a saturated aqueous solution ofammonium chloride then partitioned between EtOAc (100 mL) and water (100 mL). Theorganic layer was concentrated in vacuo and the residue purified by flash columnchromatography on silica, eluting with EtOAc/petroleum ether (1:3) to afford the desired material (270 mg, 11%) as a yellow solid.Mass Spectrum: mlz (ES+)[M+H]+ = 225
With n-butyllithium In tetrahydrofuran at -78 - 30℃; for 2.16667h; Inert atmosphere; 1 Intermediate Bl: N,N-Dimethyl-3-[5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)pyridin-2-yl]oxypropan-l-amine n-Butyllithium (2.5 M, 0.147 L, 368.21 mmol) was added dropwise to 3-(5-bromopyridin- 2-yl)oxy-N,N-dimethylpropan-l -amine (73.4 g, 283.24 mmol) and 2-isopropoxy-4,4,5,5- tetramethyl-l,3,2-dioxaborolane (68.5 g, 368.21 mmol) in THF (1 L) cooled to -78°C over a period of 10 minutes under an inert atmosphere. The resulting mixture was allowed to warm to ambient temperature and stirred for 2 h. The reaction mixture was quenched with a saturated aqueous solution of ammonium chloride (50 mL). The solvent was removed under reduced pressure and diluted with EtOAc (2L), the organic layer was dried over Na2S04, filtered and evaporated to afford the desired material as a yellow oil (98 g, 113 %). The product was used in the next step directly without further purification. NMR Spectrum: NMR (300MHz, CDCb) δ 1.30 (12H, s), 1.93 - 2.09 (2H, m), 2.33 (6H, s), 2.49 - 2.61 (2H, m), 4.37 (2H, t), 6.69 (1H, dd), 7.91 (1H, dd), 8.51 (1H, d).

  • 11
  • [ 1248399-37-2 ]
  • [ 2089288-23-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / 2.17 h / -78 - 30 °C / Inert atmosphere 2: chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); caesium carbonate / water; 1,4-dioxane / 5 h / 80 °C / Inert atmosphere
  • 12
  • [ 1248399-37-2 ]
  • [ 2089288-01-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / 2.17 h / -78 - 30 °C / Inert atmosphere 2: potassium carbonate; 3-(di-tert-butylphosphino)-propane-1-sulfonic acid / water; 1,4-dioxane / 2 h / 17 - 80 °C / Inert atmosphere
  • 13
  • [ 1248399-37-2 ]
  • [ 2089288-02-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: n-butyllithium / tetrahydrofuran / 2.17 h / -78 - 30 °C / Inert atmosphere 2: potassium carbonate; 3-(di-tert-butylphosphino)-propane-1-sulfonic acid / water; 1,4-dioxane / 2 h / 17 - 80 °C / Inert atmosphere 3: dichloromethane / 1 h / 17 - 30 °C / Inert atmosphere
  • 14
  • [ 1248399-37-2 ]
  • [ 2135639-94-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / 4.17 h / -78 - 18 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); caesium carbonate / water; 1,4-dioxane / 3 h / 90 °C / Inert atmosphere
  • 15
  • [ 1248399-37-2 ]
  • [ 2135639-96-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / 4.17 h / -78 - 18 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); caesium carbonate / water; 1,4-dioxane / 3 h / 90 °C / Inert atmosphere
  • 16
  • [ 1248399-37-2 ]
  • [ 2231430-04-7 ]
  • [ 2231429-71-1 ]
YieldReaction ConditionsOperation in experiment
13% Stage #1: 3-[(5-bromopyridin-2-yl)oxy]-N,N-dimethylpropan-1-amine; tert-butyl (4-((2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamoyl)oxazol-2-yl)carbamate With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 120℃; for 18h; Inert atmosphere; Sealed tube; Stage #2: With trifluoroacetic acid In dichloromethane at 20℃; for 18h; 2-Amino-N-(2-chloro-5-{6-[3-(dimethylamino)propoxy]pyridin-3-yl}phenyl)-1 ,3- oxazole-4-carboxamide (72) A microwave reaction vessel was charged with intermediate 5 (100 mg, 0.22 mmol), PdCI2(dppf) (12 mg, 0.014 mmol), potassium carbonate (50 mg, 0.36 mmol) and 3-[(5- bromopyridin-2-yl)oxy]-N,N~dimethylpropan-1 -amine (37 mg, 0.14 mmol). Dioxane (1.2 mL) and water (0.3 mL) were added, the mixture degassed with nitrogen for 5 minutes and then the vessel sealed and stirred at 120°C for 18h. The solvents were removed in vacuo and the residue passed through a 1g Isolute NH2 cartridge (eluting with 3 column volumes of MeOH). The combined eluents were removed in vacuo to give the crude product. This was dissolved in DCM (0.7 mL), treated with TFA (0.3 mL) and stirred at rt for 18h. Concentration in vacuo and purification by preparative LC-MS gave 72 (8 mg, 13%) as an off white solid; 1H NMR (400 MHz, DMSO-d6) δ ppm 9.32 (s, 1 H), 8.55 (d, J=2.3 Hz, 1 H), 8.44 (d, J=2.7 Hz, 1 H), 8.12 (s, 1 H), 7.98 (dd, J=8.9, 2.7 Hz, 1 H), 7.63 (d, J=8.7 Hz, 1 H), 7.47 (dd, J=8.7, 2.3 Hz, 1 H), 7.17 (s, 2H), 6.92 (d, J=8.9 Hz, 1 H), 4.35 - 4.31 (m, 2H), 3.33 (s, 3H), 2.48 - 2.42 (m, 2H), 2.23 (s, 3H), 1.93 - 1.86 (m, 2H); LCMS: (m/z) = 416/418 [M+H]+.
  • 17
  • [ 1248399-37-2 ]
  • [ 2304655-76-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / 4.17 h / -78 - 18 °C / Inert atmosphere 2: potassium carbonate; (bis(tricyclohexyl)phosphine)palladium(II) dichloride / 1,4-dioxane / 1 h / 80 °C / Microwave irradiation; Inert atmosphere
  • 18
  • [ 1248399-37-2 ]
  • [ 2304655-50-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / 4.17 h / -78 - 18 °C / Inert atmosphere 2: potassium carbonate; bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 1.5 h / 100 °C / Microwave irradiation; Inert atmosphere
  • 19
  • [ 1248399-37-2 ]
  • [ 2304655-78-3 ]
  • [ 2304655-77-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: n-butyllithium / tetrahydrofuran / 4.17 h / -78 - 18 °C / Inert atmosphere 2: potassium carbonate; (bis(tricyclohexyl)phosphine)palladium(II) dichloride / 1,4-dioxane / 1 h / 80 °C / Microwave irradiation; Inert atmosphere 3: carbon dioxide / methanol / Resolution of racemate; Supercritical conditions
  • 20
  • [ 1248399-37-2 ]
  • [ 2304655-84-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / 4.17 h / -78 - 18 °C / Inert atmosphere 2: caesium carbonate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) / 1,4-dioxane; water / 3 h / 100 °C / Inert atmosphere
  • 21
  • [ 1248399-37-2 ]
  • [ 2304655-89-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / 4.17 h / -78 - 18 °C / Inert atmosphere 2: caesium carbonate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) / 1,4-dioxane; water / 3 h / 100 °C / Inert atmosphere
  • 22
  • [ 1248399-37-2 ]
  • [ 2304655-91-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / 4.17 h / -78 - 18 °C / Inert atmosphere 2: potassium carbonate; (bis(tricyclohexyl)phosphine)palladium(II) dichloride / 1,4-dioxane / 1 h / 80 °C / Inert atmosphere; Microwave irradiation
  • 23
  • [ 1248399-37-2 ]
  • [ 2223058-64-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / 4.17 h / -78 - 18 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); caesium carbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere
  • 24
  • [ 1248399-37-2 ]
  • [ 2304656-13-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / 4.17 h / -78 - 18 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); caesium carbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere
  • 25
  • [ 1248399-37-2 ]
  • [ 73183-34-3 ]
  • [ 918643-56-8 ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 90℃; for 2h; Inert atmosphere;
  • 26
  • [ 1248399-37-2 ]
  • [ 2380047-08-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 2 h / 90 °C / Inert atmosphere 2: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere
  • 27
  • [ 1248399-37-2 ]
  • [ 2769140-31-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C 2: tripotassium phosphate tribasic; mesyl[(tri-t-butylphophine)-2-(2-aminobiphenyl)]palladium(II) / 1,4-dioxane / 50 °C / Inert atmosphere; Sealed tube
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C 2: tripotassium phosphate tribasic; methanesulfonato(tri-t-butylphosphino)(2’-amino-1,1'-biphenyl-2-yl)palladium(II) / 1,4-dioxane / 50 °C / Inert atmosphere; Sealed tube
  • 28
  • [ 1248399-37-2 ]
  • [ 2769140-20-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C 2: tripotassium phosphate tribasic; mesyl[(tri-t-butylphophine)-2-(2-aminobiphenyl)]palladium(II) / lithium hydroxide monohydrate; 1,4-dioxane / 50 °C / Inert atmosphere; Sealed tube
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C 2: tripotassium phosphate tribasic; methanesulfonato(tri-t-butylphosphino)(2’-amino-1,1'-biphenyl-2-yl)palladium(II) / lithium hydroxide monohydrate; 1,4-dioxane / 50 °C / Inert atmosphere; Sealed tube
  • 29
  • [ 1248399-37-2 ]
  • [ 2769140-22-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C 2: tripotassium phosphate tribasic; mesyl[(tri-t-butylphophine)-2-(2-aminobiphenyl)]palladium(II) / lithium hydroxide monohydrate; 1,4-dioxane / 4 h / 50 °C / Inert atmosphere; Sealed tube
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C 2: tripotassium phosphate tribasic; methanesulfonato(tri-t-butylphosphino)(2’-amino-1,1'-biphenyl-2-yl)palladium(II) / lithium hydroxide monohydrate; 1,4-dioxane / 4 h / 50 °C / Inert atmosphere; Sealed tube
  • 30
  • [ 1248399-37-2 ]
  • [ 2769140-28-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C 2.1: tripotassium phosphate tribasic; mesyl[(tri-t-butylphophine)-2-(2-aminobiphenyl)]palladium(II) / lithium hydroxide monohydrate; 1,4-dioxane / 50 °C / Inert atmosphere; Sealed tube 2.2: Sonication
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C 2.1: tripotassium phosphate tribasic; methanesulfonato(tri-t-butylphosphino)(2’-amino-1,1'-biphenyl-2-yl)palladium(II) / lithium hydroxide monohydrate; 1,4-dioxane / 50 °C / Inert atmosphere; Sealed tube 2.2: Sonication
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 1248399-37-2 ]

Bromides

Chemical Structure| 1289045-79-9

[ 1289045-79-9 ]

3-((4-Bromopyridin-2-yl)oxy)-N,N-dimethylpropan-1-amine

Similarity: 0.91

Chemical Structure| 1015242-41-7

[ 1015242-41-7 ]

5-Bromo-2-((1-methylpiperidin-4-yl)oxy)pyridine

Similarity: 0.87

Chemical Structure| 212961-35-8

[ 212961-35-8 ]

2-((5-Bromopyridin-2-yl)oxy)-N,N-dimethylethanamine

Similarity: 0.86

Chemical Structure| 180916-06-7

[ 180916-06-7 ]

5-Bromo-2-(2-(pyrrolidin-1-yl)ethoxy)pyridine

Similarity: 0.85

Chemical Structure| 194668-50-3

[ 194668-50-3 ]

5-Bromo-2-(piperidin-4-yloxy)pyridine

Similarity: 0.84

Ethers

Chemical Structure| 1289045-79-9

[ 1289045-79-9 ]

3-((4-Bromopyridin-2-yl)oxy)-N,N-dimethylpropan-1-amine

Similarity: 0.91

Chemical Structure| 1015242-41-7

[ 1015242-41-7 ]

5-Bromo-2-((1-methylpiperidin-4-yl)oxy)pyridine

Similarity: 0.87

Chemical Structure| 212961-35-8

[ 212961-35-8 ]

2-((5-Bromopyridin-2-yl)oxy)-N,N-dimethylethanamine

Similarity: 0.86

Chemical Structure| 180916-06-7

[ 180916-06-7 ]

5-Bromo-2-(2-(pyrrolidin-1-yl)ethoxy)pyridine

Similarity: 0.85

Chemical Structure| 194668-50-3

[ 194668-50-3 ]

5-Bromo-2-(piperidin-4-yloxy)pyridine

Similarity: 0.84

Amines

Chemical Structure| 1289045-79-9

[ 1289045-79-9 ]

3-((4-Bromopyridin-2-yl)oxy)-N,N-dimethylpropan-1-amine

Similarity: 0.91

Chemical Structure| 212961-35-8

[ 212961-35-8 ]

2-((5-Bromopyridin-2-yl)oxy)-N,N-dimethylethanamine

Similarity: 0.86

Related Parent Nucleus of
[ 1248399-37-2 ]

Pyridines

Chemical Structure| 1289045-79-9

[ 1289045-79-9 ]

3-((4-Bromopyridin-2-yl)oxy)-N,N-dimethylpropan-1-amine

Similarity: 0.91

Chemical Structure| 1015242-41-7

[ 1015242-41-7 ]

5-Bromo-2-((1-methylpiperidin-4-yl)oxy)pyridine

Similarity: 0.87

Chemical Structure| 212961-35-8

[ 212961-35-8 ]

2-((5-Bromopyridin-2-yl)oxy)-N,N-dimethylethanamine

Similarity: 0.86

Chemical Structure| 180916-06-7

[ 180916-06-7 ]

5-Bromo-2-(2-(pyrrolidin-1-yl)ethoxy)pyridine

Similarity: 0.85

Chemical Structure| 194668-50-3

[ 194668-50-3 ]

5-Bromo-2-(piperidin-4-yloxy)pyridine

Similarity: 0.84