Name: 117068-71-0|2-(Benzyloxy)-6-bromopyridine|98%
Brand: Ambeed
SKU: A524567
Price: 18.0 USD
Availability: InStock
Rating: 91 (35 reviews)

1
[ 626-05-1 ]
[ 20194-18-7 ]
[ 117068-71-0 ]

Yield	Reaction Conditions	Operation in experiment
94%	In N,N-dimethyl-formamide
	In N,N-dimethyl-formamide at 80℃;

Reference： [1]Sieburth, Scott Mc.N.; Chen, Jian-Long [Journal of the American Chemical Society, 1991, vol. 113, # 21, p. 8163 - 8164]
[2]Shiao, Min-Jen; Tarng, Kai-Yih [Heterocycles, 1990, vol. 31, # 4, p. 637 - 641]

2
[ 27992-32-1 ]
[ 100-39-0 ]
[ 117068-71-0 ]

Reference： [1]Heterocycles,1990,vol. 31,p. 819 - 824

3
[ 117068-71-0 ]
[ 33513-42-7 ]
[ 784149-95-7 ]

Yield	Reaction Conditions	Operation in experiment
73%	With sec.-butyllithium

Reference： [1]Sieburth, Scott Mc.N.; Chen, Jian-Long [Journal of the American Chemical Society, 1991, vol. 113, # 21, p. 8163 - 8164]

4
[ 117068-71-0 ]
[ 115-19-5 ]
[ 134080-69-6 ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; potassium hydroxide; copper(l) iodide; diethylamine 2.) toluene, reflux; Yield given. Multistep reaction;

Reference： [1]Sieburth, Scott Mc.N.; Chen, Jian-Long [Journal of the American Chemical Society, 1991, vol. 113, # 21, p. 8163 - 8164]

5
[ 117068-71-0 ]
[ 74-86-2 ]
C₂₆H₂₀N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine

Reference： [1]Ducharme, Yves; Wuest, James D. [Journal of Organic Chemistry, 1988, vol. 53, # 24, p. 5787 - 5789]

6
[ 117068-71-0 ]
[ 1066-54-2 ]
2-(benzyloxy)-6-((trimethylsilyl)ethynyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran for 12h; Inert atmosphere; Reflux;
97%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine

Reference： [1]Park, Jongwoo; Lang, Kai; Abboud, Khalil A.; Hong, Sukwon [Journal of the American Chemical Society, 2008, vol. 130, # 49, p. 16484 - 16485]
[2]Ducharme, Yves; Wuest, James D. [Journal of Organic Chemistry, 1988, vol. 53, # 24, p. 5787 - 5789]

7
[ 27992-32-1 ]
[ 100-39-0 ]
[ 117068-71-0 ]
1-benzyl-6-bromopyridin-2(1H)-one [ No CAS ]

Reference： [1]Tetrahedron Letters,1995,vol. 36,p. 8917 - 8920
[2]Organic Letters,2015,vol. 17,p. 3382 - 3385

8
[ 117068-71-0 ]
[ 5140-72-7 ]

Reference： [1]Journal of Chemical Research - Part S,1996,p. 194 - 195

9
[ 626-05-1 ]
[ 100-51-6 ]
[ 117068-71-0 ]

Yield	Reaction Conditions	Operation in experiment
99.9%	With potassium hydroxide; 18-crown-6 ether In toluene for 1h; Heating;
90%	Stage #1: benzyl alcohol With sodium hydride In tetrahydrofuran for 0.5h; Stage #2: 2,6-Dibromopyridine In tetrahydrofuran at 20℃; for 18h;	20.1 Step l0.30 g (12 mmol) of sodium hydride was dispersed in anhydrous THF in a dried flask provided with nitrogen gas, benzylalcohol (12 mmol) was added thereto, and the mixture was stirred for 30 mins. After adding 2.4 g (10 mmol) of2,6-dibromopyridine thereto, the reaction mixture was kept at room temperature for 18 hrs, and the reaction was completed by adding water thereto. The resulting solution was extracted 3 times with ethyl acetate, and the formed organic layer was washed with a saturated NaCl solution, dried over anhydrous magnesium sulfate, and concentrated under a reduced pressure. The resulting residue was subjected to silica gel column chromatography(n-hexane:ethylacetate=19:l) to obtain 2-benzyloxy-6-bromopyridine (yield: 90%).
79%	With sodium hydride In N,N-dimethyl-formamide at 0 - 100℃; for 18h;	5.1 1) 2-Bromo-6-benzyloxypyridine To an eggplant-shaped flask, 528 mg (11 mmol) of sodium hydride having a content of 50% and 5 mL of dimethylformamide were added, and the mixture was stirred. The reaction vessel was cooled to 0° C., and 1.73 mL (10.0 mmol) of benzyl alcohol dissolved in 5 mL of dimethylformamide was gradually added dropwise thereto. To this reaction vessel, 2.37 g (10 mmol) of 2,6-dibromopyridine was added, and the mixture was heated to 100° C. and stirred for 18 hours. Subsequently, the reaction mixture was separated into aqueous and organic layers by the addition of water and ethyl acetate, and the recovered organic layer was washed with a 1 M aqueous sodium hydroxide solution and saturated saline, dehydrated over sodium sulfate, and then filtered through a cotton plug. The solvent in the filtrate was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the compound of interest as a colorless oil (2.08 g, yield: 79%). (0088) 1H-NMR (500 MHz, CDCl3, rt): δ 5.37 (2H, s), 6.75 (1H, d, J=8.0 Hz), 7.09 (1H, d, J=8.0 Hz), 7.32-7.49 (6H, m) ppm (0089) ESI MS (positive): [M+Na]+ Found m/z 286

78%	With sodium hydride In tetrahydrofuran
71%	With 18-crown-6 ether; potassium hydroxide In toluene at 130℃;
55%	With sodium hydride In N,N-dimethyl-formamide at 90℃; for 18h;
55%	Stage #1: benzyl alcohol With sodium hydride Stage #2: 2,6-Dibromopyridine	1 Example 1: Synthesis of fluorescent chemosensor substructures 1-4. Reagents and conditions: a) NaH, BNOH, then 2,6-dibromopyridine (55%); b) n-BuLi, ArBr; ZINC12 ; then 2-benzyloxy-6-bromopyridine and cat. Pd (PPh3) 4 (70%); c) H2, cat. Pd/C; d) TF20, Py (79%, two steps); e) ArB (OH) 2, cat. Pd (OAC) 2, cat. BINAP, CS2CO3 (64%); f) n-BuLi, ArBr; ZNC12 ; then 2-bromopyridine and cat. Pd (PPH3) 4 (46%); g) as (F) (57%).
26.7%	Stage #1: benzyl alcohol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 2h; Inert atmosphere; Stage #2: 2,6-Dibromopyridine In tetrahydrofuran; mineral oil Inert atmosphere;
	With potassium hydroxide; 18-crown-6 ether In toluene
	With sodium hydride In N,N-dimethyl-formamide
	With potassium hydroxide In toluene	20.a 3-Amino-4-[3-(3-Hydroxy-2-Pyridyl)Anilino]-3-Cyclobutene-1,2-Dione (a) A stirred mixture of 2,6-dibromopyridine (3.55 g), benzyl. alcohol (1.63 g), potassium hydroxide (1.68 g), 18-Crown-6 (0.20 g) and toluene (25 ml) is heated under reflux for 30 minutes. The cool solution washed with water and brine, dried (MgSO4) and evaporated to give an oil which is vacuum-distilled (Kugelrohr) to give 3.85 g of 2-benzyloxy-6-bromopyridine, bp 220-225° C./1.0 mm.

Reference： [1]Doyle, Allan A.; Parsons, Simon; Solan, Gregory A.; Winpenny, Richard E. P. [Journal of the Chemical Society, Dalton Transactions, 1997, # 12, p. 2131 - 2137]
[2]Current Patent Assignee: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; CHEMON INC. - WO2008/153325, 2008, A1 Location in patent: Page/Page column 46-47
[3]Current Patent Assignee: JAPAN SCIENCE AND TECHNOLOGY AGENCY - US2016/297764, 2016, A1 Location in patent: Paragraph 0087-0089
[4]Heo, Jung-Nyoung; Young, Seob Song; Bum, Tae Kim [Tetrahedron Letters, 2005, vol. 46, # 27, p. 4621 - 4625]
[5]Smith, Charlotte L.; Hirschhäuser, Christoph; Malcolm, Georgia K.; Nasrallah, Daniel J.; Gallagher, Timothy [Synlett, 2014, vol. 25, # 13, p. 1904 - 1908]
[6]Fang, Albert G.; Mello, Jesse V.; Finney, Nathaniel S. [Organic Letters, 2003, vol. 5, # 7, p. 967 - 970]
[7]Current Patent Assignee: UNIVERSITY OF CALIFORNIA - WO2004/46103, 2004, A2 Location in patent: Page 38
[8]Pei, Zhonghua; Blackwood, Elizabeth; Liu, Lichuan; Malek, Shiva; Belvin, Marcia; Koehler, Michael F. T.; Ortwine, Daniel F.; Chen, Huifen; Cohen, Frederick; Kenny, Jane R.; Bergeron, Philippe; Lau, Kevin; Ly, Cuong; Zhao, Xianrui; Estrada, Anthony A.; Truong, Tom; Epler, Jennifer A.; Nonomiya, Jim; Trinh, Lan; Sideris, Steve; Lesnick, John; Bao, Linda; Vijapurkar, Ulka; Mukadam, Sophie; Tay, Suzanne; Deshmukh, Gauri; Chen, Yung-Hsiang; Ding, Xiao; Friedman, Lori S.; Lyssikatos, Joseph P. [ACS Medicinal Chemistry Letters, 2013, vol. 4, # 1, p. 103 - 107]
[9]Wash, Paul L.; Maverick, Emily; Chiefari, John; Lightner, David A. [Journal of the American Chemical Society, 1997, vol. 119, # 16, p. 3802 - 3806]
[10]Thomson, Christopher G.; Beer, Margaret S.; Curtis, Neil R.; Diggle, Helen J.; Handford, Emma; Kulagowski, Janusz J. [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 3, p. 677 - 680]
[11]Current Patent Assignee: ASTELLAS PHARMA INC. - US6211220, 2001, B1

10
[ 117068-71-0 ]
[ 95924-34-8 ]
[ 188990-86-5 ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 3802 - 3806

11
[ 117068-71-0 ]
[ 536-74-3 ]
[ 192822-62-1 ]

Yield	Reaction Conditions	Operation in experiment
70%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In diethylamine for 20h; Ambient temperature;

Reference： [1]Doyle, Allan A.; Parsons, Simon; Solan, Gregory A.; Winpenny, Richard E. P. [Journal of the Chemical Society, Dalton Transactions, 1997, # 12, p. 2131 - 2137]

12
[ 117068-71-0 ]
[ 1079-66-9 ]
[ 307498-11-9 ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: 2-(benzyloxy)-6-bromopyridine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: chloro-diphenylphosphine In tetrahydrofuran at -78 - 20℃; Further stages.;

Reference： [1]Akazome; Suzuki; Shimizu; Henmi; Ogura [Journal of Organic Chemistry, 2000, vol. 65, # 21, p. 6917 - 6921]

13
[ 27060-75-9 ]
[ 117068-71-0 ]
[ 521958-78-1 ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: 4-bromo-3-methylanisole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h; Stage #2: With zinc(II) chloride In tetrahydrofuran; hexane for 0.25h; Stage #3: 2-(benzyloxy)-6-bromopyridine In tetrahydrofuran; hexane for 16h; Heating;

Reference： [1]Fang, Albert G.; Mello, Jesse V.; Finney, Nathaniel S. [Organic Letters, 2003, vol. 5, # 7, p. 967 - 970]

14
[ 123-75-1 ]
[ 117068-71-0 ]
[ 861884-94-8 ]

Yield	Reaction Conditions	Operation in experiment
95%	at 150℃; for 0.166667h; Microwave;	7.1.1 In a dried microwave reactor, 526 mg (2.0 mmol) of 2-(benzyloxy)-6-bromopyridine and 1.70 ml (20 mmol) of pyrrolidine were placed, and the mixture was reacted using microwave at 150°C for 10 min. The reaction mixture was mixed with 20 ml of water, extracted twice with 100 ml portions of ethyl acetate, and the organic layer was separated dried over anhydrous and kept under a reduced pressure to remove the solvent. The residue thus obtained was subjected to column chromatography using 10% ethyl acetate/hexane as an eluent to obtain 485 mg (yield 95%) of 2-(benzyloxy)-6-(pyrrolidin-1-yl)pyridine
92%	With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 120℃; for 0.166667h; microwave irradiation;
92%	With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 120℃; for 0.166667h; Microwave;	7.1.2 In a dried microwave reactor into which an argon gas was introduced, , 526 mg (2.0 mmol) of 2- (benzyloxy)-6-bromopyridine, µl (2.4 mmol) of pyrrolidine, 283 mg (2.8 mmol) of sodium t-butoxide, 9 mg (0.005 mmol) of tris(dibenzylideneacetone)dipalladium(O) (0.5 mol% of Pd), 19 mg (0.015 mmol, 1.5 mol%) of (No.) -BINAP and 3 ml of toluene were placed, followed by stirring and reacting the mixture using microwave at 120°C for 10 min. The reaction mixture was diluted with 20 ml of ethyl acetate, filtered through Cellite, and kept under a reduced pressure to remove the solvent. The residue was subjected to column chromatography using 10% ethyl acetate/hexane as an eluent to obtain 470 mg (yield 92%) of 2-(benzyloxy)-6-(pyrrolidin-1-yl)pyridine. ¹H NMR (300 MHz, CDC13) 8 7.48-7.23 (m, 6H), 6.03-5.99 (m, 1H), 5.89-5.85 (m, 1H), 5.36 (s, 2H), 3.45-3.39 (m, 4H), 2.00-1.93 (m, 4H); MS (EI) M+ calc. 164.095 for C9H12N20, found 254 (23, M+), 163 (52), 91 (100), 70 (40), 65 (40)

Reference： [1]Current Patent Assignee: OSCOTEC INC; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY - WO2005/123054, 2005, A1 Location in patent: Page/Page column 34-35
[2]Heo, Jung-Nyoung; Young, Seob Song; Bum, Tae Kim [Tetrahedron Letters, 2005, vol. 46, # 27, p. 4621 - 4625]
[3]Current Patent Assignee: OSCOTEC INC; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY - WO2005/123054, 2005, A1 Location in patent: Page/Page column 34-35

15
[ 110-89-4 ]
[ 117068-71-0 ]
[ 861884-92-6 ]

Yield	Reaction Conditions	Operation in experiment
87%	With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 120℃; for 0.166667h; microwave irradiation;