[ CAS No. 17965-78-5 ] {[proInfo.proName]}

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Quality Control of [ 17965-78-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 17965-78-5 ]

Product Details of [ 17965-78-5 ]

CAS No. :	17965-78-5	MDL No. :	MFCD04113794
Formula :	C₈H₅BrN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PDZZZAWKYMHGLA-UHFFFAOYSA-N
M.W :	209.04	Pubchem ID :	3446442
Synonyms :

Safety of [ 17965-78-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 17965-78-5 ]

* 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 [ 17965-78-5 ]

[ 17965-78-5 ] Synthesis Path-Downstream 1~11

Yield	Reaction Conditions	Operation in experiment
	Rk. mit KNH2/NH3(l);

Yield	Reaction Conditions	Operation in experiment
	2-(p-Toluolsulfonyl)hydrazid-3-brom-1,8-naphthyridin-hydrobromid 8, wss. Na2CO3, (neben Naphthyridin 2);
	Verb. 7, 1.1 Aequiv. Br2 (neben Verb. 9);
	Verb. 10, 1.1 Aequiv. Br2 (neben Verb. 9);

	5-Bromo-2-amino-pyridine, Glycerol, Na-m-nitro-benzenesulfonate, FeSO4, H3BO3, conc. H2SO4, Δ;
	1,8-Naphthyridin, Br2;
	(yield)4.8 percent;

3
[ 1201845-57-9 ]
[ 17965-78-5 ]
[ 1201842-57-0 ]

Yield	Reaction Conditions	Operation in experiment
67%	With sodium carbonate In 1,4-dioxane at 100℃; for 5h;	44 EXAMPLE 44; N-(2-chloro-5-(l,8-naphthyridin-3-yl)-3-pyridinyl)-4- fluorobenzenesulfonamide; (Some starting materials may be obtained from Princeton Biomolecular Research,Inc., Monmouth Junction, NJ) To a 50 mL round-bottomed flask was added 3-bromo-l,8- naphthyridine (73 mg, 351 μmol), N-(2-chloro-5-(l,5-dimethyl-2,4-dioxa-bicyclo[3.1.0]hexan-3- yl)pyridin-3-yl)-4-fluorobenzenesulfonamide (140 mg, 351 μmol), tetrakis(triphenylphosphine)palladium (41 mg, 35 μmol), sodium carbonate (351 μl, 702 μmol), dioxane (3 ml). The reaction mixture was stirred at 100 0C for 5 h. The mixture was cooled down to room temperature. The reaction mixture was diluted with water (1 mL) and extracted with CH2Cl2 (5 x 20 mL). The organic extract was washed with saturated NaCl (2 mL), dried over Na2SO4, filtered and concentrated in vacuo and the residue was purified by silica gel chromatography, eluting with 10%MeOH/CH2Cl2 to give N-(2-chloro-5-(l,8-naphthyridin-3- yl)pyridin-3-yl)-4-fluorobenzenesulfonamide (98 mg, 67% yield) as a white solid. MS (ESI pos. ion) m/z calc'd for Ci9H12ClFN4O2S: 414.0; found 415.0. 1H NMR (300 MHz, MeOD) δ ppm 7.30 (t, J=8.77 Hz, 2 H) 7.76 (dd, J=8.18, 4.38 Hz, 1 H) 7.89 (dd, J=8.99, 5.04 Hz, 2 H) 8.44 (d, J=2.34 Hz, 1 H) 8.62 (dd, J=8.18, 1.90 Hz, 1 H) 8.70 (d, J=2.34 Hz, 1 H) 8.79 (d, J=2.48 Hz, 1 H) 9.15 (dd, J=4.38, 1.90 Hz, 1 H) 9.39 (d, J=2.48 Hz, 1 H)

Reference： [1]Current Patent Assignee: AMGEN INC - WO2009/155121, 2009, A2 Location in patent: Page/Page column 107

4
[ 1112983-31-9 ]
[ 17965-78-5 ]
[ 1201842-57-0 ]

Yield	Reaction Conditions	Operation in experiment
67%

Reference： [1]Location in patent: experimental part Nishimura, Nobuko; Siegmund, Aaron; Liu, Longbin; Yang, Kevin; Bryan, Marian C.; Andrews, Kristin L.; Bo, Yunxin; Booker, Shon K.; Caenepeel, Sean; Freeman, Daniel; Liao, Hongyu; McCarter, John; Mullady, Erin L.; San Miguel, Tisha; Subramanian, Raju; Tamayo, Nuria; Wang, Ling; Whittington, Douglas A.; Zalameda, Leeanne; Zhang, Nancy; Hughes, Paul E.; Norman, Mark H. [Journal of Medicinal Chemistry, 2011, vol. 54, # 13, p. 4735 - 4751]

5
3-phenylethynyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzoic acid methyl ester [ No CAS ]
[ 17965-78-5 ]
2-1,8-naphthyridin-3-yl-3-(phenylethynyl)benzoic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate In 1,4-dioxane; dichloromethane; water at 100℃; for 4h; Inert atmosphere;	115 24,--Aiphthyrzdin.-3-.y/.-3--’phenyethynyt) benzoic ac/cl methyl ester: stirring suspension of 3-phenyiethynyi-2-( ,4,5,5-tetramethyl- I ,3,2-dioxaboroian-2-yl)-benzoic acid methyl ester (500 mg, 1.38 mmoi), 3-bromo-1,8-naphthyridine (289 mg, 1.38 mmol) and potassium carbonate (380 rng, 2.76 rnmoi) in 1,4-dioxane: water (4:1) (10 mL) was deaerated using an argon gas balloon for 15 minutes. To the resulting suspension, [i,1’-bis (diphenylphosphino)ferrocene paliadium(11) dichloride coniplexed with dichloromethane (112 rug, 0.138 mniol) was added andreaction mixture was refiuxed at 100 °C for 4 h. The resultant reaction mixture was then allowed to cool to ambient temperature, diluted with ethyl acetate (150 mL) and filtered through celite bed. The organic layer thus obtained washed with water (2 x 30 mL), brine (30 mL). dried (anhydrous sodium sulfate). filtered and concentrated under reduced pressure to obtain crude product as a brown liquid. The crude product thus obtained was purified using silica gel cartridge eluiing with hexane / ethylacetate to give a pale yellow solid with 40 % yield

Reference： [1]Current Patent Assignee: WISTAR INSTITUTE - WO2016/183534, 2016, A1 Location in patent: Page/Page column 142

6
[ 1060735-14-9 ]
[ 17965-78-5 ]
C₃₈H₂₄N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium phosphate; copper(l) iodide; trans-1,2-cyclohexanediamine In toluene at 120℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube;	Synthesis of Compound 1 The oven-dried resealable Schlenk tube 3-Bromo-1,8-naphthyridine (357 mg, 1.7 mmol), 9-phenyl-9H, 9'H-3,3'-bicarbazole (764 mg, 1.87 mmol) Copper iodide (65 mg, 0.34 mmol), Was charged with K3PO4 (902 mg, 4.25 mmol), emptied and refilled with argon. Subsequently, trans-1,2-cyclohexanediamine (97 mg, 0.68 mmol) and dry Toluene (3.4 mL) was added under argon. The Schlenk tube was sealed with a Teflon valve, The reaction mixture was stirred at 120 & lt; 0 & gt; C for 24 hours. The resulting dark orange solution was cooled to room temperature, After diluting with dichloromethane (DCM) (50 mL) and ammonium hydroxide solution (50 mL) And the mixture was stirred at room temperature for 1 hour. The organic phase was separated and the aqueous phase And extracted with DCM (50 mL x 3). The combined organic phases were dried over magnesium sulphate and then filtered. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel (EA / DCM / triethylamine 1: 5: 0.01) A pure product of Compound 1 (748 mg, 82%) was obtained.

Reference： [1]Current Patent Assignee: UNIVERSAL DISPLAY CORP - KR2015/124914, 2015, A Location in patent: Paragraph 0162-0164

7
N-(4-(9H-carbazol-3-yl)phenyl)-N-phenyl dibenzo[b,d]furan-2-amine [ No CAS ]
[ 17965-78-5 ]
C₄₄H₂₈N₄O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With potassium phosphate; copper(l) iodide; trans-1,2-cyclohexanediamine In toluene at 120℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube;	Synthesis of Compound 2 The oven-dried resealable shrink tubing was coated with 3-bromo-l, 8-naphthyridine (357 mg, 1.7 mmol) N- (4- (9H-Carbazol-3- Yl) phenyl) -N- Phenyl dibenzo [B, d] furan-2-amine (936 mg, 1.87 mmol), Copper iodide (65 mg, 0.34 mmol), K3PO4 Mg, 4.25 mmol), emptied and refilled with argon. Then, trans-1,2-cyclohexanediamine (97 mg, 0.68 mmol), And dry toluene (3.4 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve, The reaction mixture At 120 ° C And stirred for 24 hours. The resulting dark orange solution was cooled to room temperature, After diluting with DCM (50 mL) and ammonium hydroxide solution (50 mL) And the mixture was stirred at room temperature for 1 hour. The organic phase was separated and the aqueous phase And extracted with DCM (50 mL x 3). The combined organic phases were dried over magnesium sulfate, Filtered. The filtrate was concentrated, The residue was purified by flash chromatography on silica gel (EA / DCM / triethylamine 1: 5: 0.01) A pure product of Compound 2 (780 mg 73%) was obtained.

Reference： [1]Current Patent Assignee: UNIVERSAL DISPLAY CORP - KR2015/124914, 2015, A Location in patent: Paragraph 0165-0166

8
5,8-dihydro-indolo[2,3-C]carbazole [ No CAS ]
[ 17965-78-5 ]
C₂₆H₁₆N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium t-butanolate In toluene at 100℃; for 5h;	2.1 The synthesis method is as follows: (1) In a reaction flask, 25.6 g (100 mmol) of 5,8-dihydroindolo (2,3-c) carbazole, 3-bromonaphthyridine (100 mmol), and Pd2 (dba) 30.9 g (0.785 mmol, 0.5%) were added. ), 1500 mL of toluene and 40 g (300 mmol) of sodium tert-butoxide, reacted at 100 ° C for 5 h; after the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water, ethyl acetate extraction, concentrated, and organic phase column chromatography , The obtained solid was purified by recrystallization from toluene to obtain white powder M1;

Reference： [1]Current Patent Assignee: YANTAI XIANHUA CHEM-TECH CO LTD - CN110776513, 2020, A Location in patent: Paragraph 0038; 0040-0042

9
5,8-dihydro-indolo[2,3-C]carbazole [ No CAS ]
[ 17965-78-5 ]
C₄₄H₂₈N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium t-butanolate / toluene / 5 h / 100 °C 2: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium t-butanolate / 5,5-dimethyl-1,3-cyclohexadiene / 12 h / 140 °C

Reference： [1]Current Patent Assignee: YANTAI XIANHUA CHEM-TECH CO LTD - CN110776513, 2020, A

10
1-(cyclopropylmethyl)-3-(4-methyl-5-((trimethylsilyl)ethynyl)thiazol-2-yl)urea [ No CAS ]
[ 17965-78-5 ]
1-(5-((1,8-naphthyridin-3-yl)ethynyl)-4-methylthiazol-2-yl)-3-(2-(cyclopropylmethoxy)ethyl)urea hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8.6%	Stage #1: 1-(cyclopropylmethyl)-3-(4-methyl-5-((trimethylsilyl)ethynyl)thiazol-2-yl)urea; 3-bromo-1,8-naphthyridine With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; triethylamine In tetrahydrofuran at 65℃; for 1h; Inert atmosphere; Stage #2: With hydrogenchloride

Reference： [1]Bandarage, Upul K.; Aronov, Alex M.; Cao, Jingrong; Come, Jon H.; Cottrell, Kevin M.; Davies, Robert J.; Giroux, Simon; Jacobs, Marc; Mahajan, Sudipta; Messersmith, David; Moody, Cameron S.; Swett, Rebecca; Xu, Jinwang [ACS Medicinal Chemistry Letters, 2021, vol. 12, # 1, p. 129 - 135]

11
[ 73183-34-3 ]
[ 17965-78-5 ]
3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,8-naphthyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; for 12h; Inert atmosphere;

Reference： [1]Yu, Wensheng; Liu, Jian; Clausen, Dane; Yu, Younong; Duffy, Joseph L.; Wang, Ming; Xu, Shouning; Deng, Lin; Suzuki, Takao; Chung, Christine C.; Myers, Robert W.; Klein, Daniel J.; Fells, James I.; Holloway, M. Katharine; Wu, Jin; Wu, Guoxin; Howell, Bonnie J.; Barnard, Richard J. O.; Kozlowski, Joseph [Journal of Medicinal Chemistry, 2021, vol. 64, # 8, p. 4709 - 4729]

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H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 17965-78-5 ] {[proInfo.proName]}

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Product Details of [ 17965-78-5 ]

Safety of [ 17965-78-5 ]

Application In Synthesis of [ 17965-78-5 ]

[ 17965-78-5 ] Synthesis Path-Downstream 1~11

Related Functional Groups of [ 17965-78-5 ]

Bromides

Related Parent Nucleus of [ 17965-78-5 ]

Naphthyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 17965-78-5 ]

Related Parent Nucleus of
[ 17965-78-5 ]