[ CAS No. 1248399-37-2 ]

Name: 1248399-37-2|3-((5-Bromopyridin-2-yl)oxy)-N,N-dimethylpropan-1-amine|95%
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Product Details of [ 1248399-37-2 ]

CAS No. :	1248399-37-2	MDL No. :	MFCD14652180
Formula :	C₁₀H₁₅BrN₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	259.14 g/mol	Pubchem ID :	-
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 1~11

1
[ 766-11-0 ]
[ 3179-63-3 ]
[ 1248399-37-2 ]

Yield	Reaction Conditions	Operation 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.

Reference： [1]Current Patent Assignee: Helmholtz Association; EBERHARD KARLS UNIVERSITÄT TÜBINGEN - EP3992191, 2022, A1 Location in patent: Paragraph 0051-0053
[2]Current Patent Assignee: Helmholtz Association; EBERHARD KARLS UNIVERSITÄT TÜBINGEN - EP3992191, 2022, A1 Location in patent: Paragraph 0051-0053
[3]Current Patent Assignee: ASTRAZENECA PLC - WO2015/170081, 2015, A1 Location in patent: Page/Page column 67-68
[4]Current Patent Assignee: ASTRAZENECA PLC - WO2017/162605, 2017, A1 Location in patent: Page/Page column 43; 61
[5]Current Patent Assignee: ASTRAZENECA PLC - WO2019/57757, 2019, A1 Location in patent: Page/Page column 54; 55
[6]Current Patent Assignee: ASTRAZENECA PLC - WO2017/46216, 2017, A1 Location in patent: Page/Page column 52
[7]Current Patent Assignee: Helmholtz Association; EBERHARD KARLS UNIVERSITÄT TÜBINGEN - EP3992191, 2022, A1

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