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CAS No. : | 960298-00-4 | MDL No. : | MFCD13190654 |
Formula : | C12H10BrNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZBTZIRNIUHLSSJ-UHFFFAOYSA-N |
M.W : | 264.12 | Pubchem ID : | 53217389 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With silver carbonate; In benzene; at 55℃;Absence of light; | Example 22; ralphac-(35',4i?)-4-[2-(benzyloxy)pyridin-4-yl]-iV-cyclopropyl-4-hydroxy-iV-[3-(2-methoxyethoxy)-5- (3 -methoxypropyl)benzyl]piperidine-3 -carboxamide; Step 1 : 2-(benzyloxy')-4-bromopyridine; A flame-dried round bottom was charged with 4-bromopyridin-2-ol (1 eq.), benzene (0.14 M), Ag2CO3 (0.6 eq.) and benzyl bromide (1.2 eq.) under N2. The reaction was heated to 55 0C overnight in the dark. The reaction was then cooled and filtered, washing with dichloromethane. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography (SiO2; 2-4% Et2O in hexanes) to give the desired product as a clear oil.; Example 44; i?flc-(3S,4R)-4-(l-butyl-2-oxo-l,2-dihydropyridin-4-yl)-N-cyclopropyl-4-methoxy-N-[3-(2- methoxyethoxy)-5 -(3 -methoxypropyl)berizyl]piperidme-3 -carboxamide; Step 1 : 2-(benzyloxy)-4-bromopyridine; A flame-dried round-bottom flask was charged with 4-bromo-2-pyridinol (1 eq.) benzene (0.14 M solution), Ag2CO3 (0.6 eq) and benzyl bromide (1.2 eq.) and heated to 55 0C in the dark for 15 h. The reaction mixture was cooled to rt, filtered through celite, washing with <n="61"/>CH2Cl2, and the filtrate concentrated in vacuo. The residue was purified by flash chromatography (SiO2; 2-4% Et2O in hexanes) to afford the title compound as a clear, colorless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step 2: rac-tert-bxxtv (3£4i?V4-r2-fbeiizyloxy)pyridin-4-yll-3-('{cvclopropyir3-(2- methoxyethoxy)-5-(3-methoxypropyl)benzyll amino } carbonyl)-4-hydroxypiperidine- 1 - carboxylate; To a solution of <strong>[960298-00-4]2-(benzyloxy)-4-bromopyridine</strong> from the previous step (1 eq.) inTHF (0.1M) at -78 0C was added n-BuLi (2.5 M in hexanes, 2.1 eq.). The mixture was stirred for30 min at -78 0C. MgBr2 (solid, 2.5 eq.) was added, and the resulting mixture stirred at -78 0C for 20 min, and 30 min at 0 0C. A solution of ketoamide 3.1 in THF (0.04 M) was added and the resulting mixture stirred at 0 0C for Ih and rt for 0.5 h. The reaction was quenched with saturated aqueous NH4Cl solution and extracted 2 x Et2O. The combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by automated flash chromatography (SiO2; 0-15% acetone in toluene) to afford the title compound as a clear colorless oil. | ||
Step 2: mc-tert-butyl O£4i?V4-r2-(benzyloxy)pyridin-4-yl1-3-alphacvclopropyP-(2- methoxyethoxyV 5-(3 -methoxypropyDbenzyl] amino ) carbonylM-hydroxypiperidine- 1 - carboxylate; To a solution of the title compound from step 1 (1.47 eq.) in THF (0.3 M) at -78 0C was added n-BuLi (2.5 M in hexanes, 1.6 eq.). The resulting solution was stirred at -78 0C for 30 min. MgBr2 (0.5 M in Et2O, 1.9 eq.) was added, and the resulting solution was stirred at -78 0C for 30 min. A solution of ketoamide 3.1 (0.1 M in THF, 1 eq.) was added, and the reaction mixture warmed to rt over 16 h, quenched with NaHCO3 (aq., sat.), extracted with 2 x EtOAc. The combined organic phases were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by automated flash chromatography (SiO2; 10- 80% EtOAc in hexanes) to afford the title compound as a clear, colorless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With potassium tert-butylate; In tetrahydrofuran; at 0℃;Inert atmosphere; | Example 19i2-(Benzyloxy)-4-bromopyridine4-Bromo-2-fluoropyridine (5.28 g, 30 mmol) and benzyl alcohol (3.24 g, 30.00 mmol) were dissolved in dry THF (50 mL) under an atmosphere of argon. The solution was cooled with an external ice/water bath and held at 0 0C. Potassium tert-butoxidc (3.37 g, 30.00 mmol) was added in portions (approx. 100 mg each) under efficient stirring over a period of 20 min. Stirring at 0 0C was continued for 60 min, whereafter the cooling bath was removed and the mixture was stirred at rt for 30 min. Water (5 mL) was added to the reaction mixture and most of the THF was evaporated under reduced pressure. The remaining mixture was partitioned between pentane (75 mL) and water (50 mL). The organic phase was separated, washed with water (2x25 mL), dried over MgSO4 and the solvents removed in vacuo to afford 7.86 g (99%) of the title compound.1H NMR (500 MHz, DMSO-J6) delta 8.10 (d, IH) 7.44 (d, 2H) 7.38 (t, 2H) 7.33 (t, IH) 7.25 (d, IH) 7.20 (s, IH) 5.36 (s, 2H). |
dibenzo-18-crown-6; In toluene; for 3h;Dean-Stark conditions; Reflux; | Arene 1; 2-(Benzyloxy)-4-bromopyridine; To a solution of 4-bromo-2-fluoropyridine (1 eq.), benzyl alcohol (1.2 eq.) and dibenzo-18-crown-6 (0.05 eq.) in toluene (0.4 M) was added potassium hydroxide (2 eq.). A Dean-Stark apparatus was then attached and the reaction suspension was heated at reflux for 3 h. After cooling to RT, the reaction mixture was diluted with hexanes and then filtered through a pad of celite. Concentration of the filtrate in vacuo afforded a yellow oil. Purification of the crude product thus obtained by way of column chromatography (SiO2, 97:3 (v/v) Hex : Et2O) afforded the title compound as a colorless oil. | |
With potassium hydroxide;dibenzo-18-crown-6; In toluene; for 3h;Inert atmosphere; Reflux; | To a solution of 4-bromo-2-fluoropyridine (1 eq.), benzyl alcohol (1.2 eq.) and dibenzo-18-crown-6 (0.05 eq.) in toluene (0.4 M) was added potassium hydroxide (2 eq.). A Dean-Stark apparatus was then attached and the reaction suspension was heated at reflux for 3 h. After cooling to RT, the reaction mixture was diluted with hexanes and then filtered through a pad of celite. Concentration of the filtrate in vacuo afforded a yellow oil. Purification of the crude product thus obtained by way of column chromatography (SiO2, 97:3 (v/v) Hex : Et2O) afforded the title compound as a colorless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step 2: tert-Butyl tralphan5-4-[2-(benzyloxy)-4-pyridinyl]-3-({cyclopropyl[3-(2-methoxyethoxy)-5- (3 -methoxypropyl)benzyl] amino } carbonyl)-4-hydroxy- 1 -piperidinecarboxylate; To a THF solution (0.08 M) of Arene 1 was added at -780C rc-butyl lithium (2.5 M solution in hexanes, 2.1 eq.). After stirring at -780C for 30 min, solid magnesium bromide (2.5 eq.) was added in one rapid portion and the resulting mixture was stirred at -780C for 20 min. The reaction mixture was then slowly warmed to O0C over 30 min and f°rt-butyl 3- ( { cyclopropyl [3 -(2-methoxyethoxy)-5 -(3 -methoxypropyl)ben:zyl] amino } carbonyl)-4-oxo- 1 - piperidinecarboxylate (1 eq.) from the previous step was added as a THF solution. The reaction mixture was then stirred at O0C for 1 h and at RT for 30 min. The reaction was then quenched with the addition of sat. aq. NH4Cl and ether. The aqueous layer was separated and back- extracted with ether. The combined organic extracts were washed further with brine, dried over MgSO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of column chromatography (SiO2, 96:4 -> 93:7 (v/v) acetone: toluene) afforded the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With silver carbonate; In benzene; at 20 - 50℃; for 40h;Protection from light; | A mixture of 4-Bromo-1H-pyridin-2-one (0.613 g), silver carbonate (0.63 g) and benzyl bromide (0.50 mL) in benzene (10 mL) was heated at 50C for 24 hours, protected from light. Reaction mixture stirred ambient temperature for 16 hours. Reaction mixture was filtered through a pad of CELITE, which was washed ethyl acetate. The filtrate was concentrated and purified by flash column chromatography (silica gel, 0 to 10% ethyl acetate/hexanes) to give 2-Benzyloxy-4-bromo-pyridine (0.6043 g): LCMS-ESI+: calc'd for C12H11BrNO: 265.12 (M+H+); Found: 263.8, 265.8 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 80 - 90℃; for 8h; | A mixture of 2-Benzyloxy-4-bromo-pyridine (0.292 g), 2-{5-[4-(4,4,5,5- Tetramethyl-(1,3,2)-ldioxaborolan-2-yl)-phenyl)-1H-imidazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.533 g, prepared according to WO2008021927 A2) and Pd(PPh3)4 (0.064 g) in aq. K2CO3 solution/dimethoxyethane (1.82 mL/5.0 mL) was heated at 80-90C for 8 hours. Reaction mixture was cooled, diluted with ethyl acetate, washed with brine, dried (MgSO4) and concentrated. The residue was purified by flash column chromatography (silica gel, 20 to 80% ethyl acetate/hexanes) to give 2-{5-[4-(2-Benzyloxy-pyridin-4-yl)-phenyl]-1H-imidazol-2-yl}- pyrrolidine-1-carboxylic acid tert-butyl ester (0.530 g): LCMS-ESI+: calc'd for C30H33N4O3: 497.6 (M+H+); Found: 497.0 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.3 g | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; for 6h;Reflux; | (2) A mixed solution comprising 0.28 g of <strong>[960298-00-4]2-(benzyloxy)-4-bromopyridine</strong>, 0.28 g of (2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)boronic acid, 0.060 g of tetrakis(triphenylphosphine)palladium, 0.29 g of potassium carbonate, 2 mL of 1 ,4- dioxane and 2 mL of water, was heated and refluxed for 6 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. Then, the organic layer was washed with water and an aqueous sodium chloride solution, and anhydrous sodium sulfate was added for drying. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n- heptane/ethyl acetate=15/1) to obtain 0.30 g of the oily desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46.3% | To a solution of phenylmethanol (2.248 g, 20.79 mmol) in THF (100 mL), was added NaH (60% w/w) (0.914 g, 22.86 mmol) at 0C. The reaction mixture was stirred at 0C for 4 hr. 4-bromo-2- chloropyridine (2 g, 10.39 mmol) in THF (50 mL) was added dropwise into the reaction mixture at 0 C. The reaction mixture was stirred at 25C for overnight. The reaction mixture was partitioned between EtOAc (100 mL) and water (100 mL). The organic phase was washed with saturated brine (100 mL), dried over sodium sulphate and evaporated in vacuo to give the crude product. The crude product was purified by Combi-Flash chromatography on a silica column (24g) and eluted with EtOAc/petroleum (0-100% over 10 min, 100% over 5 min). Appropriate fractions were evaporated to give the title compound (1.272 g, 4.82 mmol, 46.3 % yield) as a white oil. LCMS: MH+ =264/266 | |
0.71 g | (1) 0.37 g of sodium hydride was added to a mixed solution comprising 1.1 g of benzyl alcohol and 3 mL of tetrahydrofuran while cooling with an ice bath, followed by stirring at room temperature for 10 minutes. A mixed solution comprising 0.60 g of 4- bromo-2-chloropyridine and 1 mL of tetrahydrofuran, was added to the reaction solution, followed by heating and refluxing for 3 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. Then, the organic layer was washed with water and an aqueous sodium chloride solution, and anhydrous sodium sulfate was added for drying. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n- heptane/ethyl acetate=10/1) to obtain 0.71 g of oily 2-(benzyloxy)-4-bromopyridine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62%; 13%; 12% | With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 20℃; for 16h; | To a solution of CuBr2 (536 mg, 2.4 mmol) in acetonitrile (6 mL) was addedtBuONO (356 muL, 3.0 mmol) and the mixture was stirred for 15 min. A solution of 2-benzyloxy-4-aminopyridine 6 (400.5 mg, 2.0 mmol) in acetonitrile (4 mL) was addedand the mixture was stirred for 16h. After concentration under reduced pressure, aq.15% ammonia solution was added and the aqueous layer was extracted with ethylacetate (3x). The combined organic layers were dried (Na2SO4), filtered andconcentrated under reduced pressure. Purification by flash chromatography on silicagel (hexane/DCM: 80/20) first yielded 2-benzyloxy-3, 4, 5-tribromopyridine 7c (97mg, 12%) as a colorless solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With hydrogenchloride; In methanol;Reflux; | To a solution of <strong>[960298-00-4]2-benzyloxy-4-bromopyridine</strong> 6 (201 mg, 0.8 mmol) in MeOH(4.5 mL) was added conc. HCl (2.3 mL). The mixture was heated at reflux overnight.Then the reaction mixture was cooled to room temperature and concentrated underreduced pressure. The residue was poured into cold water and carefully quenchedwith aq. sat. Na2CO3. The aqueous layer was extracted with ethyl acetate (3x). Thecombined organic layers were washed with brine, dried (Na2SO4), filtered andconcentrated under reduced pressure. The crude was purified by flash chromatography on silica gel (EtOAc/MeOH: 98/2) to give 1c (109 mg, 82%) as acolorless solid. Data for 1c are reported above. |
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