Name: 57744-67-9|6-Iodo-2,3-dihydrobenzo[b][1,4]dioxine|98%
Brand: Ambeed
SKU: A434516
Rating: 97 (30 reviews)

1
[ 930-88-1 ]
[ 57744-67-9 ]
[ 598-25-4 ]
5-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-2,6-dimethyl-3a,4,7,7a-tetrahydroisoindole-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; triphenylphosphine; silver carbonate In toluene at 90℃; for 48h;

Reference： [1]Brown, Stephen; Grigg, Ronald; Hinsley, Joanne; Korn, Stewart; Sridharan, Visuvanathar; Uttley, Michael D [Tetrahedron, 2001, vol. 57, # 52, p. 10347 - 10355]

2
[ 57744-67-9 ]
[ 463-49-0 ]
C₁₀H₁₃NO₄ [ No CAS ]
3a-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-7,8-dimethoxy-1-methyl-1,3a,4,9b-tetrahydro-3H-chromeno[4,3-c]isoxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With caesium carbonate; triphenylphosphine In toluene at 120℃; for 48h;

Reference： [1]Aftab, Tajassas; Grigg, Ronald; Ladlow, Mark; Sridharan, Visuvanathar; Thornton-Pett, Mark [Chemical Communications, 2002, # 16, p. 1754 - 1755]

3
[ 57744-67-9 ]
[ 463-49-0 ]
(o-C₆H₄OH)C(H)N(Me)O [ No CAS ]
3a-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-1-methyl-1,3a,4,9b-tetrahydro-3H-chromeno[4,3-c]isoxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With caesium carbonate; triphenylphosphine In toluene at 120℃; for 48h;

Reference： [1]Aftab, Tajassas; Grigg, Ronald; Ladlow, Mark; Sridharan, Visuvanathar; Thornton-Pett, Mark [Chemical Communications, 2002, # 16, p. 1754 - 1755]

4
[ 493-09-4 ]
[ 57744-67-9 ]

Reference： [1]Catalysis science and technology,2014,vol. 4,p. 4308 - 4312
[2]Molecules,2005,vol. 10,p. 401 - 406

5
[ 57744-67-9 ]
[ 890316-40-2 ]
tert-butyl 2-((2,3-dihydrobenzo[1,4]dioxin-6-yl)amino)-4-phenylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 20℃; for 48h; Heating / reflux;	116 To toluene 3.0mL suspension of tert-butyl 2-amino-4-phenylbenzoate 0.10g, rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl 2.3mg, palladium acetate 0.8mg and cesium carbonate 0.24g was added 2,3-dihydro-6-iodobenzo[1,4]dioxin 0.24g, and it was heated and refluxed for 24 hours. After the reaction mixture was cooled to room temperature, rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl 2.3mg and palladium acetate 0.8mg were added, and it was heated and refluxed for 24 hours. After the reaction mixture was cooled to room temperature, insoluble matter was filtrated, and ethyl acetate and 10% citric acid aqueous solution were added to it. The organic layer was separated and collected, dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Trikonex company, Flash Tube 2008, eluent; hexane:ethyl acetate=10:1] to give tert-butyl 2-((2,3-dihydrobenzo[1,4]dioxin-6-yl)amino)-4-phenylbenzoate. Trifluoroacetic acid 3.0mL solution of the obtained tert-butyl 2-((2,3-dihydrobenzo[1,4]dioxin-6-yl)amino)-4-phenylbenzoate was stirred at room temperature for 3 hours. The solvent was removed under reduced pressure, and the obtained residue was refined by reversed-phase silica gel column chromatography [eluent; 70-100% acetonitrile/0.1% trifluoroacetic acid aqueous solution] to give 2-((2,3-dihydrobenzo[1,4]dioxin-6-yl)amino)-4-phenylbenzoic acid 5mg of a yellow solid. 1H-NMR(DMSO-d6) δ value: 4.24(4H,s),6.79-6.82(2H,m),6.88(1H,d,J=8.6Hz),6.99(1H,dd,J=8.3,1.7Hz),7 .21(1H,s),7.37-7.41(1H,m),7.43-7.47(2H,m),7.53-7.55(2H,m),7.95(1H,d,J=8.3Hz),9.46-9.54(1H,broad),12.94-13.07(1H,broad).

Reference： [1]Current Patent Assignee: FUJIFILM HOLDINGS CORP. - EP1860098, 2007, A1 Location in patent: Page/Page column 93-94

6
[ 57744-67-9 ]
[ 910240-70-9 ]
tert-butyl 4-((E)-2-(2,3-dihydrobenzo[1,4]dioxin-6-yl)vinyl)-2-(4-fluoroanilino)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate In toluene at 20 - 110℃; for 24h;	131 To toluene 3.0mL solution of tert-butyl 2-(4-fluoroanilino)-4-vinylbenzoate 0.12g were added 2,3-dihydro-6-iodobenzo[1,4]dioxin 0.20g, cesium carbonate 0.25g, tetrabutylammonium bromide 37mg and polymer-carried bis(acetato)triphenylphosphine palladium(II) 58mg at room temperature, and it was stirred at 110°C for 24 hours. After the reaction mixture was cooled to room temperature, insoluble matter was filtrated, ethyl acetate and 10% citric acid aqueous solution were added to it. The organic layer was separated and collected, dried over anhydrous magnesium sulfate after sequential washing with 10% citric acid aqueous solution and saturated sodium chloride aqueous solution, the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Trikonex company, Flash Tube 2008, eluent; hexane:ethyl acetate=4:1] to give tert-butyl 4-((E)-2-(2,3-dihydrobenzo[1,4]dioxin-6-yl)vinyl)-2-(4-fluoroanilino)benzoate. Trifluoroacetic acid 10mL solution of the obtained tert-butyl 4-((E)-2-(2,3-dihydrobenzo[1,4]dioxin-6-yl)vinyl)-2-(4-fluoroanilino)benzoate was stirred at room temperature for 1 hour. The solvent was removed under reduced pressure to give 4-((E)-2-(2,3-dihydrobenzo[1,4]dioxin-6-yl)vinyl)-2-(4-fluoroanilino)benzoic acid 17mg of pale yellow solid. 1H-NMR(DMSO-d6) δ value: 4.24(4H,s),6.83(1H,d,J=8.3Hz),7.00-7.15(6H,m),7.20-7.26(2H,m),7.29-7.36(2H,m),7.86(1H,d,J=8.3Hz),9.60(1H,s),12.83-13.08(1H,broad).

Reference： [1]Current Patent Assignee: FUJIFILM HOLDINGS CORP. - EP1860098, 2007, A1 Location in patent: Page/Page column 99-100

7
[ 57744-67-9 ]
[ 16205-84-8 ]
(2,3-dihydro-benzo[1,4]dioxin-6-yl)-propynoic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With silver(I) chloride In N,N-dimethyl-formamide at 50℃; for 12h;

Reference： [1]Lecercle, Delphine; Mothes, Celine; Taran, Frederic [Synthetic Communications, 2007, vol. 37, # 8, p. 1301 - 1311]

8
[(triisopropylsilanyl)-ethynyl]-phosphonic acid diethyl ester [ No CAS ]
[ 57744-67-9 ]
(2,3-dihydro-benzo[1,4]dioxin-6-ylethynyl)-phosphonic acid diethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With silver(I) chloride In N,N-dimethyl-formamide at 50℃; for 12h;

Reference： [1]Lecercle, Delphine; Mothes, Celine; Taran, Frederic [Synthetic Communications, 2007, vol. 37, # 8, p. 1301 - 1311]

9
[ 675-20-7 ]
[ 57744-67-9 ]
[ 943997-48-6 ]

Yield	Reaction Conditions	Operation in experiment
56%	With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine In 1,4-dioxane at 85℃; for 20h;

Reference： [1]Norman, Mark H.; Zhu, Jiawang; Fotsch, Christopher; Bo, Yunxin; Chen, Ning; Chakrabarti, Partha; Doherty, Elizabeth M.; Gavva, Narender R.; Nishimura, Nobuko; Nixey, Thomas; Ognyanov, Vassil I.; Rzasa, Robert M.; Stec, Markian; Surapaneni, Sekhar; Tamir, Rami; Viswanadhan, Vellarkad N.; Treanor, James J. S. [Journal of Medicinal Chemistry, 2007, vol. 50, # 15, p. 3497 - 3514]

10
C₃₃H₄₀BF₃N₄O₃ [ No CAS ]
[ 57744-67-9 ]
C₃₅H₃₅F₃N₄O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate In 1,4-dioxane at 70℃;	3.A Under Argon, the 6-boronate 8 (15 mg, 0.025 mmol) in dioxane (2.0 mL) was added to the flask which was charged with Pd (dppf) Cl2 (2 mg), Cs2C03 (17 mg, 0.055 MMOL), and 3,4- ethylenedioxyiodobenzene (15 mg, 0.057 mmol). The mixture was thoroughly DEGASSED by alternately connected the flask to vacuum and Argon. The resulting solution was heated to 70 °C and stirred overnight. It was diluted by EtOAc after cooled to room temperature. The solid was removed by filter through CELITE and washed by some EtOAc. Concentration to remove the solvent and the resulting residue purified by LC to give product 9. Exact Mass is 616 and LC-MS showed 617 (M++1).

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2004/80463, 2004, A1 Location in patent: Page/Page column 109-110

11
[ 57744-67-9 ]
[ 766-81-4 ]
[ 1035267-43-6 ]

Yield	Reaction Conditions	Operation in experiment
94%	With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; at 20℃; for 72h;	To a mixture of bis(triphenylphosphine)palladium(II) dichloride (134 mg, 0.191 mmol), copper(I) iodide (36 mg, 0.191 mmol) and triethylamine (15 mL) in anhydrous tetrahydrofuran (65 mL) under an atmosphere of argon were sequentially added a solution of 6-iodobenzodioxane (5.00 g, 19.08 mmol) in anhydrous tetrahydrofuran (15 mL) and a solution of <strong>[766-81-4](3-bromophenyl)acetylene</strong> (3.63 g, 20.03 mmol) in anhydrous tetrahydrofuran (10 mL). The resulting solution was stirred at room temperature for 3 days. The crude mixture was diluted with ethyl acetate, washed sequentially with 1 M hydrochloric acid, water and saturated aqueous sodium hydrogen carbonate, dried over magnesium sulfate and concentrated in vacuo. Purification by column chromatography, using ethyl acetate in heptane (0-15%) as the eluent, gave the title compound in 94% yield: 1H NMR (CDCl3) 5 7.67 (t, J= 1.6 Hz5 1 H), 7.42 - 7.46 (m, 2 H), 7.21 (t, J= 8.0 Hz, 1 H), 7.01 - 7.06 (m, 2 H), 6.84 (d, J= 7.8 Hz, 1 H), 4.26 - 4.31 (m, 4 H); MS (EI) m/z 3U, 316 [M+.].

Reference： [1]Patent: WO2008/76046,2008,A1 .Location in patent: Page/Page column 173-174

12
[ 57744-67-9 ]
[ 1123158-30-4 ]

Yield	Reaction Conditions	Operation in experiment
20%	Stage #1: 6-iodo-1,4-benzodioxane With n-butyllithium In tetrahydrofuran; hexanes at -70℃; for 0.583333h; Stage #2: With zinc(II) chloride In tetrahydrofuran; hexanes at -70 - 0℃; Stage #3: In tetrahydrofuran; hexanes at 20 - 65℃; for 24h;	22.1 Step 1: Preparation of 4-[3-{6-[3-bromo-5-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-phenoxy]-hexyl}-(2-(2-ethoxycarbonyl-ethyl)-phenoxy)-butyric acid ethyl ester; To a solution of 3,4-ethylenedioxyiodobenzene (1.31 g, 5.0 mmol) in dry tetrahydrofuran (10 mL) was added n-butyllithium (2.2 mL, 5.5 mmol, 2.5 M) in hexanes at -70° C. for 5 minutes. After addition, some white precipitate was formed and the suspension was stirred for 30 minutes at this temperature. Then, a solution of anhydrous zinc chloride (1.64 g, 12.0 mmol) (anhydrous zinc chloride can be obtained by heating commercial zinc chloride with heat gun under high vacuum until it melts and then cool down to room temperature before dissolve) in dry tetrahydrofuran (8 mL) was added at -70° C. The resulting clear solution was allowed to warm to 0° C. by removing the cooling bath. In a separate reaction flask, bis(dibenzylidene-acetone)palladium(0) (288 mg, 0.5 mmol) and tri-tolylphosphine (608 mg, 2.0 mmol) in dry tetrahydrofuran (5 mL) was stirred for 10 min under nitrogen at room temperature and then treated with 4-{3-[6-(3,5-dibromo-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester (2.56 g, 4.0 mmol) in dry tetrahydrofuran (10 mL) and the above freshly prepared zinc compound in dry tetrahydrofuran at room temperature. The resulting brick red suspension was heated to 60-65° C. for 24 h. Then, the reaction mixture was cooled to room temperature and then diluted with saturated ammonium chloride solution (100 mL). The organic compound was extracted into ethyl acetate (3×75 mL) and the combined organic extracts were washed with brine solution (200 mL). The organic layers were dried over anhydrous magnesium sulfate and filtration of the drying agent and concentration of the solvent gave the crude product which was purified by using an ISCO 80 g column, eluting with 0-20% ethyl acetate in hexanes to isolate 4-[3-{6-[3-bromo-5-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-phenoxy]-hexyl}-(2-(2-ethoxycarbonyl-ethyl)-phenoxy)-butyric acid ethyl ester (579 mg, 20%) as a light yellow oil: ES(+)-HRMS m/e calculated for C37H45BrO8 (M+Na)+ 719.2190, found 719.2191.

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2009/54466, 2009, A1 Location in patent: Page/Page column 47-48

13
[ 57744-67-9 ]
[ 58521-27-0 ]
[ 1206164-16-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With copper(l) iodide In diethylene glycol dimethyl ether at 130℃; for 24h; Inert atmosphere;

Reference： [1]Shang, Rui; Fu, Yao; Wang, Yan; Xu, Qing; Yu, Hai-Zhu; Liu, Lei [Angewandte Chemie - International Edition, 2009, vol. 48, # 49, p. 9350 - 9354]

14
[ 57744-67-9 ]
C₃₆H₃₂N₂O₈ [ No CAS ]
[ 1195074-65-7 ]

Yield	Reaction Conditions	Operation in experiment
74%	With silver orthophosphate; C₄₅H₃₈N₂O₂; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In tetrahydrofuran at 20 - 80℃; Inert atmosphere; optical yield given as %ee; enantioselective reaction;

Reference： [1]Shu, Wei; Ma, Shengming [Chemical Communications, 2009, # 41, p. 6198 - 6200]

15
[ 57744-67-9 ]
[ 155303-91-6 ]

Yield	Reaction Conditions	Operation in experiment
12%	With N-iodo-succinimide; CF₃COOH In acetonitrile	3.a Step 3a. Step 3a. 6,7-Diiodo-2,3-dihydrobenzo[b][1,4]dioxine (Compound 0102-5) To a solution of 6-iodo-2,3-dihydrobenzo[b][1,4]dioxine (2 g, 14.7 mmol) in acetonitrile (60 ml) was added NIS (9.92 g, 44.1 mmol) followed by CF3COOH (3.35 g, 29.4 mmol). The mixture was stirred at room temperature overnight. The reaction mixture was concentrated and purified by column chromatography on silica gel (Petroleum ether) to provide the title compound 0102-5 as a white solid (0.7 g, 12%): 1H NMR (DMSO-d6) δ 4.21 (s, 4H), 7.34 (s, 2H).
12%	With N-iodo-succinimide; trifluoroacetic acid In acetonitrile at 20℃;	3.3a Step 3a. 6,7-Diiodo-2,3-dihydrobenzo[b][1,4]dioxine (Compound 0102-5) Step 3a. 6,7-Diiodo-2,3-dihydrobenzo[b][1,4]dioxine (Compound 0102-5) (0165) To a solution of 6-iodo-2,3-dihydrobenzo[b][1,4]dioxine (2 g, 14.7 mmol) in acetonitrile (60 ml) was added NIS (9.92 g, 44.1 mmol) followed by CF3COOH (3.35 g, 29.4 mmol). The mixture was stirred at room temperature overnight. The reaction mixture was concentrated and purified by column chromatography on silica gel (Petroleum ether) to provide the title compound 0102-5 as a white solid (0.7 g, 12%): 1H NMR (DMSO-d6) δ 4.21 (s, 4H), 7.34 (s, 2H).

Reference： [1]Current Patent Assignee: CURIS INC - US2010/184801, 2010, A1
[2]Current Patent Assignee: CURIS INC - US2016/317508, 2016, A1 Location in patent: Paragraph 0165

16
[ 57744-67-9 ]
[ 1228692-98-5 ]
tert-butyl 2,3-dihydrobenzo[b][1,4]dioxin-6-yl(3-perfluorooctylpropoxy)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine In toluene at 110℃; for 16h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Nielsen, Simon Dalsgaard; Smith, Garrick; Begtrup, Mikael; Kristensen, Jesper L. [European Journal of Organic Chemistry, 2010, # 19, p. 3704 - 3710]

17
[ 273-53-0 ]
[ 57744-67-9 ]
[ 201230-82-2 ]
[ 1258498-76-8 ]

Yield	Reaction Conditions	Operation in experiment
72%	With copper(l) iodide; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; 1,3-bis-(diphenylphosphino)propane; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20 - 130℃; Inert atmosphere; Autoclave;

Reference： [1]Wu, Xiao-Feng; Anbarasan, Pazhamalai; Neumann, Helfried; Beller, Matthias [Angewandte Chemie - International Edition, 2010, vol. 49, # 40, p. 7316 - 7319]

18
[ 100-42-5 ]
[ 57744-67-9 ]
[ 201230-82-2 ]
[ 343609-17-6 ]

Yield	Reaction Conditions	Operation in experiment
87%	With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; 2-((di-adamantan-1-yl)phosphaneyl)-1-(2,6-diisopropylphenyl)-1H-imidazole; triethylamine In 1,4-dioxane at 100℃; for 20h; Autoclave;

Reference： [1]Wu, Xiao-Feng; Neumann, Helfried; Spannenberg, Anke; Schulz, Thomas; Jiao, Haijun; Beller, Matthias [Journal of the American Chemical Society, 2010, vol. 132, # 41, p. 14596 - 14602]

19
[ 57744-67-9 ]
[ 109-77-3 ]
[ 4442-54-0 ]

Yield	Reaction Conditions	Operation in experiment
53%	Stage #1: 6-iodo-1,4-benzodioxane; malononitrile With copper(l) iodide; caesium carbonate; <i>L</i>-proline In dimethyl sulfoxide at 130℃; for 24h; Inert atmosphere; Stage #2: In dimethyl sulfoxide at 140℃; for 12h; Stage #3: With hydrogenchloride In water

Reference： [1]Yang, Daoshan; Yang, Haijun; Fu, Hua [Chemical Communications, 2011, vol. 47, # 8, p. 2348 - 2350]

20
[ 22013-33-8 ]
[ 57744-67-9 ]

Yield	Reaction Conditions	Operation in experiment
94.22%	Stage #1: 6-amino-3,4-benzodioxane With hydrogenchloride; sodium nitrite In water at -5 - 0℃; for 0.5h; Inert atmosphere; Stage #2: With potassium iodide In water at 0 - 5℃; Inert atmosphere;	4.2 2.4.2. 6-Iodo-1,4-benzodioxane (2) A mechanically stirred mixture of 6-amino-1,4-benzodioxane (5.29 g, 35 mmol) and 36 % HCl (50 mL) was cooled to -5 °C. A solution of NaNO2 (2.90 g, 42 mmol) in 20 mL H2O was cooled to 0 °C and slowly added while maintaining the temperature at -5 °C. The final solution was stirred at 0 °C for 30 min. A solution of KI (11.62 g, 70 mmol) in 30 mL H2O was added dropwise keeping the temperature between 0 and 5 °C. The resulting mixture was stirred overnight and extracted twice with diethyl ether. The organic layer was consecutively washed with a concentrated NaHSO3 solution, 5 % NaOH and water and dried over MgSO4. The solvent was removed under reduced pressure and the crude product was purified by column chromatography using silica gel and dichloromethane-hexane (3:2; v/v) as the eluent to give 2, a pale yellow oil phase (8.64 g, 94.22%). 1H NMR (500 MHz, d6-DMSO, ppm): δ 7.18 (s, 1H), 7.13 (d, J = 8.45 Hz, 1H), 6.68 (d, J = 8.45 Hz, 1H), 4.22 (s, -OCH2CH2O-, 4H).
86%	Stage #1: 6-amino-3,4-benzodioxane With hydrogenchloride; sodium nitrite In water at 0℃; for 0.416667h; Stage #2: With urea In water for 0.25h; Stage #3: With potassium iodide In dichloromethane; water at 20℃;	6-Iodo-2,3-dihydrobenzo[b][l,4]dioxine (S9-2).; 2,3-dihydrobenzo[b][l,4]dioxin-6-amine (S9-1; 5 g, 33 mmol) was dissolved in 10% HCl solution and cooled to 0°C. Then, 30 mL of a cold aqueous solution of NaN02 (4.6 g, 66 mmol) was added over a period of 15 min and the reaction mixture was stirred at 0°C for an additional 10 min, followed by the addition of urea (1.6 g, 27 mmol). After 15 min, 40 mL of a suspension of KI (16.5 g, 100 mmol) in water/CH2Cl2 (1:1) was added. The reaction mixture was stirred overnight at roomtemperature then extracted with CH2C12, dried over MgS0 . And condensed under reduced pressure and the residue was purified by flash chromatography (hexane:EtOAc, 100:0 to 90:10) to afford S9-2 (7.4 g, 86%) as a colorless oil. 1H NMR (500 MHz, CDC13) δ 7.28 δ (s, 1H), 7.13 (d, J= 8.5 Hz, 1H), 6.63 (d, J= 8.5 Hz, 1H), 4.27-4.24 (m, 4H).

Reference： [1]Kim, Se Hun; Choi, Jun; Sakong, Chun; Namgoong, Jin Woong; Lee, Woosung; Kim, Dong Hoe; Kim, Boeun; Ko, Min Jae; Kim, Jae Pil [Dyes and Pigments, 2015, vol. 113, p. 390 - 401]
[2]Current Patent Assignee: MEMORIAL SLOAN-KETTERING CANCER CENTER - WO2011/44394, 2011, A1 Location in patent: Page/Page column 110

21
[ 7390-62-7 ]
[ 57744-67-9 ]
[ 1289544-98-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium t-butanolate In N,N-dimethyl-formamide at 110℃; for 24h;	8- (7-Iodo-2,3-dihydrobenzo[b\| [l,4]dioxin-6-ylthio)-9H-purin-6-amine (S9-3).; To a solution of S9-2 (1.26 g, 4.8 mmol) in DMF (15 mL) was added 8-mercaptoadenine (0.400 g, 2.4 mmol), neocuproine (0.056 g, 0.24 mmol), Cul (0.044 g, 0.24 mmol) and NatOBu (0.460 g, 4.8 mmol). The reaction mixture was stirred at 110 °C for 24h. Solids were filtered and the filtrate was condensed under reduced pressure. The residue was flash chromatographed (CHCl3:MeOH:AcOH, 60:0.5:0.5 to 30:0.5:0.5) to yield 0.578 g (80%) of intermediate coupling product (MS (ESI) m/z 301.9 [M+H]+). To 0.400 g (1.4 mmol) of this and NIS (0.945 g, 4.2 mmol) in acetonitrile (15 mL) was added TFA (540 μ, 0.800 g, 7 mmol) and the mixture Was stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue was purified by flash chromatography(CHCl3:MeOH:AcOH, 60:0.5:0.5 to 30:0.5:0.5) to give S9-3 (0.436 g, 73%). 1H NMR (DMSO-de, 500 MHz) δ 8.37 (s, 1H), 8.03 (br s, 2H), 7.47 (s, 1H), 7.10 (s, 1H), 4.25-4.27 (m, 4H); MS (ESI) m/z 427.9 [M+H]+.

Reference： [1]Current Patent Assignee: MEMORIAL SLOAN-KETTERING CANCER CENTER - WO2011/44394, 2011, A1 Location in patent: Page/Page column 110-111

22
[ 57744-67-9 ]
[ 1301169-45-8 ]
[ 103-71-9 ]
[ 1301169-72-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In acetonitrile at 70℃; for 15.5h; Inert atmosphere;

Reference： [1]Shu, Wei; Yu, Qiong; Jia, Guochen; Ma, Shengming [Chemistry - A European Journal, 2011, vol. 17, # 17, p. 4720 - 4723]

23
[ 57744-67-9 ]
[ 1316753-48-6 ]
3-benzoyl-5-(2,3 dihydrobenzo[b][1,4]dioxin-6-yl)-5(E)-3,4,7,8-tetrahydro-2H-oxocin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With palladium diacetate; potassium carbonate; triphenylphosphine In acetonitrile at 85℃; for 2.5h; Inert atmosphere; regioselective reaction;

Reference： [1]Location in patent: experimental part Wan, Baoqiang; Jia, Guochen; Ma, Shengming [Advanced Synthesis and Catalysis, 2011, vol. 353, # 10, p. 1763 - 1774]

24
[ 57744-67-9 ]
[ 768-70-7 ]
[ 1380434-09-2 ]

Yield	Reaction Conditions	Operation in experiment
72%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In N,N-dimethyl-formamide at 81℃; for 16h; Inert atmosphere;

Reference： [1]Trosien, Simon; Waldvogel, Siegfried R. [Organic Letters, 2012, vol. 14, # 12, p. 2976 - 2979]

25
[ 57744-67-9 ]
[ 329203-85-2 ]
[ 1384843-69-9 ]

Yield	Reaction Conditions	Operation in experiment
85%	With copper(l) iodide; dichlorobis(tri-O-tolylphosphine)palladium; potassium carbonate; <i>L</i>-proline In water; N,N-dimethyl-formamide for 5h; Inert atmosphere; Reflux;	General procedure for the preparation of compound 7 General procedure: To a solution of 2-methyl-4-(trimethylsilylethynyl)-thiazole (5, 5.11 mmol) in DMF (2.5 mL) was added an appropriate (hetero)aryl halide (6, 5.63 mmol, 1.1 equiv) under nitrogen. To this mixture were added PdCl2(PPh3)2 (0.042 mmol, 0.01 equiv), L-proline (0.51 mmol, 0.1 equiv), CuI (0.25 mmol, 0.05 equiv), and K2CO3 (6.24 mmol, 1.25 equiv) and water (0.15 mL). The mixture was stirred at 45-50 °C for the time mentioned in Table 3. After completion of the reaction the mixture was cooled to room temp, partitioned between EtOAc (10 mL) and 0.1 N HCl (3.0 mL). The organic layer was collected, washed with cold water (2 x 10 mL), dried over anhydrous MgSO4, filtered and concentrated under low vacuum. The residue was purified by column chromatography on silica gel using hexane-EtOAc as solvent system to give the desired product.

Reference： [1]Arunkumar; Naresh Kumar Reddy; Chandrasekhar; Rajender Kumar; Shiva Kumar; Pal, Manojit [Tetrahedron Letters, 2012, vol. 53, # 30, p. 3885 - 3889]

26
[ 57744-67-9 ]
rac-(4aR*,8aR*)-tert-butyl 2-oxohexahydro-2H-pyrido[4,3-e][1,3]oxazine-7(3H)-carboxylate [ No CAS ]
rac-(4aR*,8aR*)-tert-butyl 3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-oxohexahydro-2H-pyrido[4,3-e][1,3]oxazine-7(3H)-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.19g	With copper(l) iodide; potassium carbonate; trans-1,2-cyclohexanediamine In 1,4-dioxane at 110℃; for 40h; Inert atmosphere;	B.i B.i. Rac-(4aR,8aR)-tert-butyl 3-(2,3-dihydrobenzo[b] [1 ,4] ¹ dioxin-6-yl)-2-oxohexahydro- 2H-pyrido[4, 3-e] [1 ,3] oxazine- 7 (3H)-carboxylate: A vial was charged with K2C03 (0.22 g, 1.56 mmol, 2 eq.), Cul (0.01 g, 0.08 mmol, 0.1 eq.) and trafts-l,2-cyclohexane diamine (0.01 g, 0.08 mmol, 0.1 eq.), rac-(4aR,8aR)-tert-butyl 2-oxohexahydro-2H-pyrido[4,3-e][l,3]oxazine-7(3H)-carboxylate (Preparation A, 0.2 g, 0.78 mmol) and flushed with nitrogen for 5 min. A solution of 6-iodo- 2,3-dihydrobenzo[b][l,4]dioxine (0.21 g, 0.78 mmol, 1.01 eq.) in dry dioxane (0.78 mL) was added and the resulting suspension was at 110°C for 40 h. The reaction mixture was cooled to rt and filtered over Celite. The solid was washed by EA (2 x 10 mL). The filtrate was concentrated to dryness and the residue was purified by CC (DCM/MeOH 49: 1 to 19: 1) to give the title compound as a beige foam (0.19 g). MS (ESI, m/z): 391.2 [M+H+] for C20H26N2O6.
0.19 g	With copper(l) iodide; potassium carbonate; trans-1,2-cyclohexanediamine In 1,4-dioxane at 110℃; for 40h; Inert atmosphere;	B.i B.i. Rac-(4aR,8aR)-tert-butyl 3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-oxohexahydro-2H-pyrido[4,3-e][1,3]oxazine-7(3H)-carbox A vial was charged with K2CO3 (0.22 g, 1.56 mmol, 2 eq.), CuI (0.01 g, 0.08 mmol, 0.1 eq.) and trans-1,2-cyclohexane diamine (0.01 g, 0.08 mmol, 0.1 eq.), rac-(4aR,8aR)-tert-butyl 2-oxohexahydro-2H-pyrido[4,3-e][1,3]oxazine-7(3H)-carboxylate (Preparation A, 0.2 g, 0.78 mmol) and flushed with nitrogen for 5 min. A solution of 6-iodo-2,3-dihydrobenzo[b][1,4]dioxine (0.21 g, 0.78 mmol, 1.01 eq.) in dry dioxane (0.78 mL) was added and the resulting suspension was at 110° C. for 40 h. The reaction mixture was cooled to rt and filtered over Celite. The solid was washed by EA (2×10 mL). The filtrate was concentrated to dryness and the residue was purified by CC (DCM/MeOH 49:1 to 19:1) to give the title compound as a beige foam (0.19 g). [0251] MS (ESI, m/z): 391.2 [M+H+] for C2H26N2O6.

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2013/80156, 2013, A1 Location in patent: Page/Page column 44
[2]Current Patent Assignee: JOHNSON & JOHNSON INC - US2014/309218, 2014, A1 Location in patent: Paragraph 0250; 0251

27
[ 57744-67-9 ]
[ 10288-72-9 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 5804 - 5809

28
[ 57744-67-9 ]
1-benzyl-2,3-dihydro-2-(4-methoxyphenyl)pyridin-4(1H)-one [ No CAS ]
[ 1443017-91-1 ]

Yield	Reaction Conditions	Operation in experiment
83%	With tetrabutyl-ammonium chloride; palladium diacetate; sodium hydrogencarbonate; silver(I) chloride In dimethyl sulfoxide at 80℃; for 24h; regioselective reaction;

Reference： [1]Yu, Yi-Yun; Bi, Lei; Georg, Gunda I. [Journal of Organic Chemistry, 2013, vol. 78, # 12, p. 6163 - 6169]

29
[ 57744-67-9 ]
[ 124-38-9 ]
[ 70882-08-5 ]
3-benzyl-5-(1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)vinyl)-2-oxazolidinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In dimethyl sulfoxide at 70℃; for 8h;	7 4.2.7 3-Benzyl-5-(1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)vinyl)-2-oxazolidinone (2ag) General procedure: The reaction of Pd(PPh3)4 (17 mg, 0.015 mmol), K2CO3 (84 mg, 0.61 mmol), 1a (50 mg, 0.31 mmol), 6-iodo-2,3-dihydrobenzo[1,4]dioxine (92 mg, 0.35 mmol), and a balloon of carbon dioxide (about 1 L) in 2 mL of DMSO afforded 89 mg of 2ag (84%) as an oil (petroleum ether/ethyl acetate=4:1): 1H NMR (300 MHz, CDCl3) δ 7.38-7.24 (m, 3H, ArH), 7.23-7.12 (m, 2H, ArH), 6.85-6.70 (m, 3H, ArH), 5.43 (s, 1H, one proton of C=CH2), 5.39-5.29 (m, 2H, one proton of C=CH2 and OCH), 4.46 (d, J=15.0 Hz, 1H, one proton of CH2 in Bn), 4.33 (d, J=15.3 Hz, 1H, one proton of CH2 in Bn), 4.22 (s, 4H, OCH2CH2O), 3.56 (t, J=8.7 Hz, 1H, one proton of NCH2 in oxazolidinone ring), 3.06 (t, J=7.5 Hz, 1H, one proton of NCH2 in oxazolidinone ring); 13C NMR (75 MHz, CDCl3) δ 157.6, 144.2, 143.7, 143.4, 135.4, 130.3, 128.7, 127.80, 127.76, 119.5, 117.3, 115.3, 112.7, 73.4, 64.25, 64.17, 49.2, 48.0; MS (m/z) 337 (M+, 15.59), 293 (M+-CO2, 11.13), 91 (100); IR (neat, cm-1) ν 1753, 1578, 1505, 1431, 1294, 1251, 1194, 1100, 1060; HRMS calcd for C20H19NO4 (M+): 337.1314, found 337.1314.

Reference： [1]Li, Suhua; Ye, Juntao; Yuan, Weiming; Ma, Shengming [Tetrahedron, 2013, vol. 69, # 48, p. 10450 - 10456]

30
[ 57744-67-9 ]
[ 201230-82-2 ]
[ 3319-99-1 ]
[ 1610885-79-4 ]

Yield	Reaction Conditions	Operation in experiment
57%	With potassium acetate; sodium hydrogencarbonate In water at 120℃; for 20h; Inert atmosphere; Autoclave; regioselective reaction;

Reference： [1]Pospech, Jola; Tlili, Anis; Spannenberg, Anke; Neumann, Helfried; Beller, Matthias [Chemistry - A European Journal, 2014, vol. 20, # 11, p. 3135 - 3141]

31
[ 57744-67-9 ]
[ 51-35-4 ]
1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1H-pyrrole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With copper(II) ferrite; caesium carbonate In dimethyl sulfoxide at 100℃; for 20h; Inert atmosphere;	Representative experimental procedure for the synthesis of N-substituted pyrroles: General procedure: To astirred solution of: Aryl iodide (1.0 mmol), trans-4-Hydroxy-L-proline (1.5 mmol), nano CuFe2O4 (0.01 mmol), base (2 equiv), solvent (3.0 mL), 20h, 100 oC. The progress of the reaction was monitored by TLC. After the reaction was complete CuFe2O4 nano were placed on the bottom of the flask by a neodymium magnet, and the supernatant solution was removed. The crude residue was extracted with ethyl acetate (3 x 10 mL). The combined organic layers were extracted with water, saturated brine solution, and dried over anhydrous Na2SO4.The organic layers were evaporated under reduced pressure and the resulting crude product was purified by column chromatography to give the corresponding N-substituted pyrrole in excellent yields. The identity and purity of the product were confirmed by 1H,13C NMR, and mass spectra.

Reference： [1]Satish; Reddy, K. Harsha Vardhan; Ramesh; Kumar, B.S.P. Anil; Nageswar [Tetrahedron Letters, 2014, vol. 55, # 16, p. 2596 - 2599]

32
[ 4319-49-7 ]
[ 57744-67-9 ]
N-morpholino-2,3-dihydrobenzo[b][1,4]dioxine-6-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With sulfuric acid; palladium diacetate; caesium carbonate; sodium sulfite; tris[tert-butyl]phosphonium tetrafluoroborate In 1,4-dioxane at 80℃; for 16h; Schlenk technique; Inert atmosphere;

Reference： [1]Li, Wanfang; Li, Haoquan; Langer, Peter; Beller, Matthias; Wu, Xiao-Feng [European Journal of Organic Chemistry, 2014, vol. 2014, # 15, p. 3101 - 3103]

33
[ 57744-67-9 ]
2-(4-methoxybenzyl)-1,2-isothiazolidine-1,1-dioxide [ No CAS ]
[ 1613639-95-4 ]

Yield	Reaction Conditions	Operation in experiment
87%	With 2,2,6,6-tetramethylpiperidylzinc chloride lithium chloride; bis(dibenzylideneacetone)-palladium⁽⁰⁾; ruphos In tetrahydrofuran at 70℃; for 16h; Inert atmosphere;

Reference： [1]Rene, Olivier; Fauber, Benjamin P.; Malhotra, Sushant; Yajima, Herbert [Organic Letters, 2014, vol. 16, # 13, p. 3468 - 3471]

34
[ 57744-67-9 ]
[ 106-40-1 ]
N-(4-bromophenyl)-N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2,3-dihydrobenzo[b][1,4]dioxin-6-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60.6%	With copper(l) iodide; 1,10-Phenanthroline; potassium hydroxide In toluene at 125℃; for 24h; Inert atmosphere;	4.6 2.4.3. 4-Bromo-N,N-bis(4-methoxyphenyl)aniline (3) General procedure: To a stirred solution of 4-iodoanisole (5.85 g, 25 mmol), 4-bromoaniline (1.72 g, 10 mmol), and 1,10-phenanthroline (0.18 g, 1 mmol) in toluene (100 mL) were added potassium hydroxide (5.61 g, 100 mmol) and copper(I) iodide (0.19 g, 1 mmol). The reaction mixture was heated under reflux for 24 h at 125 °C. The crude product was extracted into dichloromethane, and the organic layer was washed with 1 N HCl solution, brine, and water. The organic layer was dried with anhydrous MgSO4 and then the solvent was removed in vacuo. The residue was purified by column chromatography using silica gel and dichloromethane-hexane (1:1; v/v) as the eluent to give 3 (2.39 g, 62.2%).

Reference： [1]Kim, Se Hun; Choi, Jun; Sakong, Chun; Namgoong, Jin Woong; Lee, Woosung; Kim, Dong Hoe; Kim, Boeun; Ko, Min Jae; Kim, Jae Pil [Dyes and Pigments, 2015, vol. 113, p. 390 - 401]

35
[ 57744-67-9 ]
[ 1403251-25-1 ]
(S)-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-(1,3-dioxoisoindolin-2-yl)-N-methoxypropanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With α-picoline; silver(I) acetate; palladium diacetate at 20 - 80℃; for 24h; Sealed tube;
76%	With α-picoline; 1,1,1,3',3',3'-hexafluoro-propanol; silver(I) acetate; palladium diacetate at 80℃; for 24h; Sealed tube;	Arylation with heteroaryl iodides General procedure for monoarylation of 25 with a heterocyclic iodide [Ar(Het)-I]: The starting material Compound 25 (0.1 mmol, 24.8 mg) , Pd(OAc)2 (10 mol%, 2.2 mg) , and AgOAc (0.2 mmol, 33.4 mg) were weighed in air and placed in a sealed tube (10 mL) with a magnetic stir bar. To the reaction mixture, aryl iodide (0.15 mmol) , 2- picoline (20 mol%, 2 μ,) , and HFIP (1.0 mL) were added. The reaction mixture was first stirred at room temperature for 10 minutes and then heated to 80 °C for 24 hours under vigorous stirring. Upon completion, the reaction mixture was cooled to room temperature, filtered with celite using DCM. The solvents were removed under reduced pressure and the resulting mixture was purified by a silica gel-packed flash chromatography column using DCM/EtOAc (1/0 to 4/1 to 2/1) as the eluent. 30a (S) -3- (2 , 3-Dihydrobenzo [b] [1 , 4] dioxin-6-yl) -2- (1 , 3-dioxoisoindolin-2-yl) ~2V-methoxy propanamide (30a) Substrate 25 was heteroarylated following the general arylation procedure. Analysis of crude reaction mixture by 1H NMR showed a > 20:1 ratio of mono- and diarylated products. After purification by column chromatography using DCM/EtOAc (1/0 to 4/1 to 2/1) as the eluent, Compound 30a was obtained as a white solid (29.0 mg, 76%) . XH NMR (600 MHz, CDC13) δ 9.23 (s, 1H) , 7.81-7.78 (m, 2H) , 7.72-7.70 (m, 2H) , 6.68 (s, 1H) , 6.65 (d, J = 7.8 Hz, 1H) , 6.60 (d, J = 7.8 Hz, 1H) , 5.02 (m, 1H) , 4.16-4.14 (m, 4H) , 3.74 (s, 3H) , 3.40 (m, 2H) ; 13C NMR (150 MHz, CDC13) δ 167.93, 166.58, 143.49, 142.54, 134.36, 131.34, 129.16, 123.63, 121.75, 117.68, 117.35, 64.51, 64.16, 54.64, 34.10; HRMS (ESI-TOF) Calcd for C20H19 2O6 [M+H]+: 383.1238; found: 383.1244.

Reference： [1]Chen, Gang; Shigenari, Toshihiko; Jain, Pankaj; Zhang, Zhipeng; Jin, Zhong; He, Jian; Li, Suhua; Mapelli, Claudio; Miller, Michael M.; Poss, Michael A.; Scola, Paul M.; Yeung, Kap-Sun; Yu, Jin-Quan [Journal of the American Chemical Society, 2015, vol. 137, # 9, p. 3338 - 3351]
[2]Current Patent Assignee: SCRIPPS RESEARCH - WO2015/131100, 2015, A1 Location in patent: Page/Page column 187; 188

36
[ 57744-67-9 ]
N-(quinolin-8-yl)-2,3-dihydrobenzo[b][1,4]dioxine-2-carboxamide [ No CAS ]
N-(quinolin-8-yl)-2,2′,3,3′-tetrahydro-[2,6′-bibenzo[b][1,4]dioxine]-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With silver(I) acetate; palladium diacetate In toluene at 110℃; for 24h; Inert atmosphere; regioselective reaction;

Reference： [1]Parella, Ramarao; Babu, Srinivasarao Arulananda [Journal of Organic Chemistry, 2015, vol. 80, # 4, p. 2339 - 2355]

37
[ 57744-67-9 ]
[ 247228-28-0 ]

Yield	Reaction Conditions	Operation in experiment
89%	With copper(ll) sulfate pentahydrate; ethane-1,2-dithiol; potassium hydroxide In water; dimethyl sulfoxide at 90℃; for 20h; Inert atmosphere;

Reference： [1]Liu, Yajun; Kim, Jihye; Seo, Heesun; Park, Sunghyouk; Chae, Junghyun [Advanced Synthesis and Catalysis, 2015, vol. 357, # 10, p. 2205 - 2212]

38
[ 57744-67-9 ]
[ 51942-34-8 ]
3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-N-[2-(methylthio)phenyl]-thiophene-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With silver(I) acetate; palladium diacetate In toluene at 110℃; for 24h; Inert atmosphere; regioselective reaction;

Reference： [1]Padmavathi, Rayavarapu; Sankar, Rathinam; Gopalakrishnan, Bojan; Parella, Ramarao; Babu, Srinivasarao Arulananda [European Journal of Organic Chemistry, 2015, vol. 2015, # 17, p. 3727 - 3742]

39
[ 110-89-4 ]
[ 57744-67-9 ]
[ 67-66-3 ]
CX-546 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With cesiumhydroxide monohydrate; palladium diacetate; bis[2-(diphenylphosphino)phenyl] ether In toluene at 80℃; for 24h; Glovebox; Inert atmosphere; Sealed tube;

Reference： [1]Gockel, Samuel N.; Hull, Kami L. [Organic Letters, 2015, vol. 17, # 13, p. 3236 - 3239]

40
[ 57744-67-9 ]
[ 7188-38-7 ]
[ 19102-07-9 ]

Yield	Reaction Conditions	Operation in experiment
94%	With copper (II) trifluoroacetate hydrate; palladium diacetate In dimethyl sulfoxide at 130℃; for 6h; Sealed tube; Inert atmosphere;	19 General procedure for the synthesis of aryl nitriles 1b-28b General procedure: Aryl iodide (0.7 mmol, 1 equiv), tert-butyl isocyanide (2.1 mmol, 237 μL, 3 equiv), Pd(OAc)2 (0.035 mmol, 8 mg, 5 mol %), Cu(TFA)2*xH2O (1.4 mmol, 405 mg, 2 equiv) and DMSO (2.5 mL) were added to a 15 mL sealed tube, and stirred at 130 °C for 4-12 h under nitrogen. After completion of the reaction indicated by TLC, the mixture was extracted with Et2O (510 mL). The combined organic phases was dried over Na2SO4, and concentrated under vacuum. Then the residue was purified by column chromatography on silica gel using petroleum ether (30-60 °C)/Et2O as eluant to provide the pure target product.

Reference： [1]Jiang, Xiao; Wang, Jin-Mei; Zhang, Ying; Chen, Zhong; Zhu, Yong-Ming; Ji, Shun-Jun [Tetrahedron, 2015, vol. 71, # 29, p. 4883 - 4887]

41
[ 57744-67-9 ]
[ 65-85-0 ]
2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With palladium diacetate; caesium carbonate; N-acetyl-L-isoleucine; silver carbonate at 30℃; for 36h; Schlenk technique; Inert atmosphere;

Reference： [1]Zhu, Changlei; Zhang, Yuanfei; Kan, Jian; Zhao, Huaiqing; Su, Weiping [Organic Letters, 2015, vol. 17, # 14, p. 3418 - 3421]

42
[ 57744-67-9 ]
[ 1111441-33-8 ]
(2R*,3S*)-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-phenyl-N-(quinolin-8-yl)butanamide [ No CAS ]
(2R*,3R*)-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-phenyl-N-(quinolin-8-yl)butanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40 % de	With silver(I) acetate; palladium diacetate In toluene at 110℃; for 24h; Overall yield = 65 %; Overall yield = 69 mg; diastereoselective reaction;	11 4.4. General procedure for the β-arylation of aliphatic carboxamides and the preparation of the racemic compounds 3a-l, 4a-c, 5a, 6a-f, 8a-c, 8eA-hA, 8eB-hB and enantiomerically enriched 10a-c General procedure: A mixture of the corresponding carboxamide ((±)-1a-h or (±)-1iA or 1iB or 1j-(S)) (0.25 mmol), Pd(OAc)2 (2.8 mg, 5 mol %), aryl iodide (1.0 mmol, 4 equiv) and AgOAc (92 mg, 0.55 mmol, 2.2 equiv) in anhydrous toluene (3 mL) was heated at 110 °C for 24-70 h (see the respective Tables/Schemes for the reaction time for the specific examples) under nitrogen atmosphere. After the reaction period, the reaction mixture was concentrated in vacuum and purification of the resulting reaction mixture by silica gel column chromatography furnished the corresponding β-C-H arylated racemic compounds 3a-l, 4a-c, 5a, 6a-f, 8a-c, 8eA-hA, 8eB-hB and enantiomerically enriched 10a-c (see Tables/Schemes for the reaction conditions for the specific examples).

Reference： [1]Gopalakrishnan, Bojan; Babu, Srinivasarao Arulananda; Padmavathi, Rayavarapu [Tetrahedron, 2015, vol. 71, # 43, p. 8333 - 8349]

43
[ 57744-67-9 ]
1-(4-methoxyphenyl)-4,5-bis{4-(trifluoromethyl)phenyl}-1H-pyrazole [ No CAS ]
3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1-(4-methoxyphenyl)-4,5-bis{4-(trifluoromethyl)phenyl}-1H-pyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With 1,10-Phenanthroline; palladium diacetate; caesium carbonate In toluene at 160℃; for 96h; Inert atmosphere; Sealed tube;

Reference： [1]Fuse, Shinichiro; Morita, Taiki; Johmoto, Kohei; Uekusa, Hidehiro; Tanaka, Hiroshi [Chemistry - A European Journal, 2015, vol. 21, # 41, p. 14370 - 14375]

44
[ 57744-67-9 ]
[ 1066-54-2 ]
1,2-bis(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)ethyne [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran; water for 18h; Inert atmosphere; Schlenk technique; Darkness;

Reference： [1]Wu, Bin; Chopra, Rena; Yoshikai, Naohiko [Organic Letters, 2015, vol. 17, # 22, p. 5666 - 5669]

45
N-(quinolin-8-yl)acrylamide [ No CAS ]
[ 57744-67-9 ]
(Z)-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-N-(quinolin-8-yl)-acrylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With silver(I) acetate; palladium diacetate In toluene at 110℃; Inert atmosphere; stereoselective reaction;

Reference： [1]Parella, Ramarao; Babu, Srinivasarao Arulananda [Journal of Organic Chemistry, 2015, vol. 80, # 24, p. 12379 - 12396]

46
[ 57744-67-9 ]
[ 201230-82-2 ]
[ 87154-95-8 ]
6-[4-(2,3-dihydro-1,4-benzodioxine-6-carbonyl)piperazin-1-yl]-1,2,3,4-tetrahydroquinolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium carbonate In 1,4-dioxane at 120℃;

Reference： [1]See, Yi Yang; Dang, Tuan Thanh; Chen, Anqi; Seayad, Abdul Majeed [European Journal of Organic Chemistry, 2014, vol. 2014, # 33, p. 7405 - 7412]

47
[ 57744-67-9 ]
[ 201230-82-2 ]
[ 116290-77-8 ]
N-{4-[4-(2,3-dihydro-1,4-benzodioxine-6-carbonyl)piperazin-1-yl]phenyl}acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With potassium carbonate In 1,4-dioxane at 120℃;

Reference： [1]See, Yi Yang; Dang, Tuan Thanh; Chen, Anqi; Seayad, Abdul Majeed [European Journal of Organic Chemistry, 2014, vol. 2014, # 33, p. 7405 - 7412]

48
[ 57744-67-9 ]
C₁₇H₂₆N₂O₃ [ No CAS ]
C₂₅H₃₂N₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With palladium diacetate; potassium carbonate; Trimethylacetic acid In 1,2-dichloro-ethane at 80℃; for 24h;

Reference： [1]Han, Jian; Liu, Pei; Wang, Chao; Wang, Qian; Zhang, Jingyu; Zhao, Yanwei; Shi, Daqing; Huang, Zhibin; Zhao, Yingsheng [Organic Letters, 2014, vol. 16, # 21, p. 5682 - 5685]

49
[ 57744-67-9 ]
methyl 2-(2-(diisopropylamino)-2-oxoacetamido)butanoate [ No CAS ]
methyl 4-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-(2-(diisopropylamino)-2-oxoacetamido)butanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With palladium diacetate; silver carbonate; Trimethylacetic acid In 1,3,5-trimethyl-benzene at 90℃; for 24h;

Reference： [1]Han, Jian; Zheng, Yongxiang; Wang, Chao; Zhu, Yan; Huang, Zhi-Bin; Shi, Da-Qing; Zeng, Runsheng; Zhao, Yingsheng [Journal of Organic Chemistry, 2016, vol. 81, # 13, p. 5681 - 5689]

50
[ 57744-67-9 ]
tert-butyl ((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)(m-tolyl)carbamate [ No CAS ]
tert-butyl (3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-methylphenyl)((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With N-(2-hydroxypyridin-3-yl)acetamide; methyl bicyclo[2.2.1]hept-2-ene-2-carboxylate; silver(I) acetate; palladium diacetate In 1,2-dichloro-ethane at 100℃; for 24h;

Reference： [1]Wang, Peng; Farmer, Marcus E.; Huo, Xing; Jain, Pankaj; Shen, Peng-Xiang; Ishoey, Mette; Bradner, James E.; Wisniewski, Steven R.; Eastgate, Martin D.; Yu, Jin-Quan [Journal of the American Chemical Society, 2016, vol. 138, # 29, p. 9269 - 9276]

51
[ 57744-67-9 ]
2-phenyl-N-(quinolin-8-yl)acetamide [ No CAS ]
2-(2,6-bis(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)phenyl)-N-(quinolin-8-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With silver(I) acetate; palladium diacetate In toluene at 110℃; for 24h; Inert atmosphere;	3 3.4 General procedure for the Pd(II)-catalyzed arylation of phenylacetamides and preparation of the compounds 4a-q/7a-f (bis arylation products), 3o,r/6a,b/8e,f/9a,b (mono arylation products) General procedure: An appropriate phenylacetamide (0.12 mmol, 1 equiv), an appropriate iodo compound (0.48 mmol, 4 equiv), Pd(OAc)2 (2.7 mg, 10 mol%), and AgOAc (50 mg, 0.3 mmol, 2.5 equiv) in anhydrous toluene (3 mL) was heated at 110 °C for 24 h under a nitrogen atmosphere. After the reaction period, the solvent was evaporated in vacuo to afford a crude reaction mixture. Purification of the crude reaction mixture by column chromatography furnished the corresponding arylated products 4a-q/7a-f (bis arylation products), 3o,r/6a,b/8e,f/9a,b (mono arylation products) (see corresponding Tables/Schemes for specific examples and reaction conditions).

Reference： [1]Bisht, Narendra; Babu, Srinivasarao Arulananda [Tetrahedron, 2016, vol. 72, # 39, p. 5886 - 5897]

52
[ 57744-67-9 ]
2-(4-chlorophenyl)-N-(quinolin-8-yl)acetamide [ No CAS ]
2-(4-chloro-2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)phenyl)-N-(quinolin-8-yl)acetamide [ No CAS ]
2-(4-chloro-2,6-bis(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)phenyl)-N-(quinolin-8-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 57% 2: 34%	With silver(I) acetate; palladium diacetate In toluene at 110℃; for 24h; Inert atmosphere;	17 3.4 General procedure for the Pd(II)-catalyzed arylation of phenylacetamides and preparation of the compounds 4a-q/7a-f (bis arylation products), 3o,r/6a,b/8e,f/9a,b (mono arylation products) General procedure: An appropriate phenylacetamide (0.12 mmol, 1 equiv), an appropriate iodo compound (0.48 mmol, 4 equiv), Pd(OAc)2 (2.7 mg, 10 mol%), and AgOAc (50 mg, 0.3 mmol, 2.5 equiv) in anhydrous toluene (3 mL) was heated at 110 °C for 24 h under a nitrogen atmosphere. After the reaction period, the solvent was evaporated in vacuo to afford a crude reaction mixture. Purification of the crude reaction mixture by column chromatography furnished the corresponding arylated products 4a-q/7a-f (bis arylation products), 3o,r/6a,b/8e,f/9a,b (mono arylation products) (see corresponding Tables/Schemes for specific examples and reaction conditions).

Reference： [1]Bisht, Narendra; Babu, Srinivasarao Arulananda [Tetrahedron, 2016, vol. 72, # 39, p. 5886 - 5897]

53
[ 57744-67-9 ]
2-(4-bromophenyl)-N-(quinolin-8-yl)acetamide [ No CAS ]
2-(4-bromo-2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)phenyl)-N-(quinolin-8-yl)acetamide [ No CAS ]
2-(4-bromo-2,6-bis(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)phenyl)-N-(quinolin-8-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 25% 2: 36%	With silver(I) acetate; palladium diacetate In toluene at 110℃; for 24h; Inert atmosphere;	19 3.4 General procedure for the Pd(II)-catalyzed arylation of phenylacetamides and preparation of the compounds 4a-q/7a-f (bis arylation products), 3o,r/6a,b/8e,f/9a,b (mono arylation products) General procedure: An appropriate phenylacetamide (0.12 mmol, 1 equiv), an appropriate iodo compound (0.48 mmol, 4 equiv), Pd(OAc)2 (2.7 mg, 10 mol%), and AgOAc (50 mg, 0.3 mmol, 2.5 equiv) in anhydrous toluene (3 mL) was heated at 110 °C for 24 h under a nitrogen atmosphere. After the reaction period, the solvent was evaporated in vacuo to afford a crude reaction mixture. Purification of the crude reaction mixture by column chromatography furnished the corresponding arylated products 4a-q/7a-f (bis arylation products), 3o,r/6a,b/8e,f/9a,b (mono arylation products) (see corresponding Tables/Schemes for specific examples and reaction conditions).

Reference： [1]Bisht, Narendra; Babu, Srinivasarao Arulananda [Tetrahedron, 2016, vol. 72, # 39, p. 5886 - 5897]

54
[ 57744-67-9 ]
N-(benzo[c][1,2,5]thiadiazol-4-yl)cyclobutanecarboxamide [ No CAS ]
N-(benzo[c][1,2,5]thiadiazol-4-yl)-2,4-bis(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)cyclobutanecarboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With silver(I) acetate; palladium diacetate In toluene at 110℃; for 16h; Inert atmosphere; diastereoselective reaction;

Reference： [1]Reddy, Chennakesava; Bisht, Narendra; Parella, Ramarao; Babu, Srinivasarao Arulananda [Journal of Organic Chemistry, 2016, vol. 81, # 24, p. 12143 - 12168]

55
[ 57744-67-9 ]
N-(benzo[c][1,2,5]thiadiazol-4-yl)-2-methylbenzamide [ No CAS ]
N-(benzo[c][1,2,5]thiadiazol-4-yl)-2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-6-methylbenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With silver(I) acetate; palladium diacetate In toluene at 110℃; for 24h; Inert atmosphere; regioselective reaction;

Reference： [1]Reddy, Chennakesava; Bisht, Narendra; Parella, Ramarao; Babu, Srinivasarao Arulananda [Journal of Organic Chemistry, 2016, vol. 81, # 24, p. 12143 - 12168]

56
[ 57744-67-9 ]
[ 667-27-6 ]
ethyl 2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2,2-difluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; tetrabutylammomium bromide; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; zinc In tetrahydrofuran at 60℃; for 12h; Inert atmosphere;

Reference： [1]Xia, Tingting; He, Lei; Liu, Yahu A.; Hartwig, John F.; Liao, Xuebin [Organic Letters, 2017, vol. 19, # 10, p. 2610 - 2613]

57
[ 57744-67-9 ]
[ 2628-16-2 ]
C₁₈H₁₆O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrabutylammomium bromide; potassium acetate; palladium diacetate In N,N-dimethyl-formamide at 80℃; for 5h; Inert atmosphere; Sealed tube;	General Procedure for Synthesis of the Compounds as Shown in the Scheme S3 General procedure: To a solution of tetrabutylammonium bromide (1.100 g, 3.33 mmol), potassium acetate (0.586 g, 3.57 mmol), and palladium acetate (0.025 g, 0.11 mmol) in DMF (20 mL) were added substituted iodobenzene (2.21 mmol) and 4-acetyloxystyrene (2.44 mmol). The reaction mixture was recharged with Argon and stirred at 80°C for 5 h in a sealed tube. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous NaCl and concentrated in vacuo. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 10:3) to afford the intermediate substituted (E)-4-styrylphenyl acetate. To a solution of triethylamine (2.0 mL) in MeOH (5 mL) was added substituted (E)-4-styrylphenyl acetate (1.36 mmol). The reaction mixture was stirred at reflux temperaturefor 3 h. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous NaCl and concentrated in vacuo. The residue was purified by column chromatography on silica gel (dichloromethane/methanol, 10:0.3) to afford pure product.

Reference： [1]Liang, Jian-Hua; Yang, Liang; Wu, Si; Liu, Si-Si; Cushman, Mark; Tian, Jing; Li, Nuo-Min; Yang, Qing-Hu; Zhang, He-Ao; Qiu, Yun-Jie; Xiang, Lin; Ma, Cong-Xuan; Li, Xue-Meng; Qing, Hong [European Journal of Medicinal Chemistry, 2017, vol. 136, p. 382 - 392]

58
[ 57744-67-9 ]
N-(3,5-bis(trifluoromethyl)phenyl)-1-(m-tolyl)methanesulfonamide [ No CAS ]
N-(3,5-bis(trifluoromethyl)phenyl)-1-(3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-methylphenyl)methanesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With isoquinoline; 2-carbomethoxynorbornene; silver(I) acetate; palladium diacetate In 1,2-dichloro-ethane at 100℃; for 24h; Sealed tube;

Reference： [1]Cheng, Guolin; Wang, Peng; Yu, Jin-Quan [Angewandte Chemie - International Edition, 2017, vol. 56, # 28, p. 8183 - 8186][Angew. Chem., 2017, vol. 129, # 28, p. 8295 - 8298,4]

59
[ 57744-67-9 ]
3-methyl-N-(quinolin-8-yl)thiophene-2-carboxamide [ No CAS ]
4-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-(quinolin-8-yl)-4H-thieno[2,3-c]pyrrol-6(5H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With silver(I) acetate; palladium diacetate In toluene at 110℃; for 48h; Inert atmosphere;

Reference： [1]Parella, Ramarao; Babu, Srinivasarao Arulananda [Journal of Organic Chemistry, 2017, vol. 82, # 14, p. 7123 - 7150]

60
[ 57744-67-9 ]
[ 1098215-58-7 ]
ethyl 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-9H-pyrido[3,4-b]indole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: 6-iodo-1,4-benzodioxane; ethyl 3-(1H-indol-3-yl)-2-isocyanopropanoate With palladium diacetate; triphenylphosphine; cesium pivalate In toluene at 80℃; for 5h; Inert atmosphere; Stage #2: In toluene at 80℃; for 4h;

Reference： [1]Tang, Shi; Wang, Jian; Xiong, Zhuang; Xie, Zeqiang; Li, Dengke; Huang, Jinbo; Zhu, Qiang [Organic Letters, 2017, vol. 19, # 20, p. 5577 - 5580]

61
[ 57744-67-9 ]
[ 767-91-9 ]
6-((2-methoxyphenyl)ethynyl)-2,3-dihydrobenzo[b][1,4]dioxine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere;

Reference： [1]Wu, Bin; Wu, Junliang; Yoshikai, Naohiko [Chemistry - An Asian Journal, 2017, vol. 12, # 24, p. 3123 - 3127]

62
[ 57744-67-9 ]
[ 1407870-35-2 ]
C₂₀H₁₄F₇NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With dichloro bis(acetonitrile) palladium(II); N-((1S,2S)-1-((R)-4-isopropyl-4,5-dihydrooxazol-2-yl)-2-methylbutyl)acetamide; silver carbonate In chloroform at 80℃; for 48h; enantioselective reaction;

Reference： [1]Wu, Qing-Feng; Wang, Xiao-Bing; Shen, Peng-Xiang; Yu, Jin-Quan [ACS Catalysis, 2018, vol. 8, # 3, p. 2577 - 2581]

63
[ 921765-53-9 ]
[ 57744-67-9 ]
(R)-6-(benzylsulfinyl)-2,3-dihydrobenzo[b][1,4]dioxine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; (R)-N-((1R)-(adamantan-1-yl)(5-(diphenylphosphanyl)-9,9-dimethyl-9H-xanthen-4-yl)methyl)-2-methylpropane-2-sulfinamide; caesium carbonate In 1,3,5-trimethyl-benzene at 60℃; for 90h; Sealed tube; Inert atmosphere; enantioselective reaction;

Reference： [1]Wang, Lei; Chen, Mingjie; Zhang, Peichao; Li, Wenbo; Zhang, Junliang [Journal of the American Chemical Society, 2018, vol. 140, # 9, p. 3467 - 3473]

64
[ 57744-67-9 ]
[ 193634-77-4 ]
(E)-3-(2,3-dihydrobenzo[b][1,4] dioxin-6-yl)-N-methoxy-N-methylacrylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With palladium diacetate; triethylamine; triphenylphosphine at 20 - 100℃; for 0.166667h; Ionic liquid; Microwave irradiation; Green chemistry;	Synthesis of a,b-unsaturated Weinreb amides: general methods for synthesis of N-methoxy-N-methylcinnamamide(3a) [54] General procedure: Method B (microwave reaction): To a microwave tube were added 2.00 cm3 of the ionic liquid, 0.009 g palladium(II) acetate (0.04 mmol), and 0.021 g triphenylphosphine(0.08 mmol) with a magnetic stirrer, and the reaction was stirred at room temperature for 5 min. Then, 0.3 cm3 triethylamine(2.15 mmol), 0.12 cm3 iodobenzene (1a,1 mmol), and 0.20 cm3 N-methoxy-N-methylacrylamide(2, 0.95 mmol) were added. The mixture was stirred at room temperature for 5 min and then subjected to microwave irradiation for 5 min at 100 C. After this time, the reaction mixture was cooled to room temperature, and the product was extracted by using diethyl ether (5 cm3 and2 9 10 cm3). The organic layers were combined, dried over magnesium sulphate, and evaporated in vacuo to afford N-methoxy-N-methylcinnamamide (3a), yield 94% as an orange oil.

Reference： [1]Otaibi, Ahmed Al; McCluskey, Adam [Monatshefte fur Chemie, 2018, vol. 149, # 3, p. 519 - 525]

65
[ 57744-67-9 ]
[ 12082-67-6 ]
C₂₅H₃₁B₁₀NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: 6-iodo-1,4-benzodioxane; 1-phenyl-o-carboranyl-2-methylamine With water; palladium diacetate; silver trifluoroacetate; acetic acid; Glyoxilic acid at 80℃; for 12h; Inert atmosphere; Stage #2: With sodium carbonate In tetrahydrofuran; water

Reference： [1]Zhang, Xiaolei; Yan, Hong [Chemical Science, 2018, vol. 9, # 16, p. 3964 - 3969]

66
[ 57744-67-9 ]
[ 124-38-9 ]
[ 19102-07-9 ]

Yield	Reaction Conditions	Operation in experiment
45%	With 1,4-diaza-bicyclo[2.2.2]octane; copper(I) oxide; phenylsilane; ammonia In 1-methyl-pyrrolidin-2-one at 130℃; for 24h; Sealed tube; chemoselective reaction;	General procedure for the cyanation of aryl iodide with CO₂ and NH₃ General procedure: Under nitrogen atmosphere, Cu2O (10 mol %), DABCO (25 mol %), and a stirring bar were added into a 10 mL oven-dried sealed glass tube (as shown in Figure S1). Then NMP (0.5 mL), aryl iodides (0.125 mmol, 1.0 equiv.) and PhSiH3 (0.75 mmol, 6 equiv.) were injected by syringe. The tube was then sealed and CO2 (0.67 mmol, 5.4 equiv., 15 mL) as well as NH3 (0.67 mmol, 5.4 equiv., 15 mL) were injected by syringe after N2 was removed under vacuum. Finally, the mixture was stirred for 24 hr in a pre-heated-to-130 °C alloyed block. After the reaction was finished, the tube was cooled to room temperature and the pressure was carefully released. The yield of were measured by GC analysis using dodecane as the internal standard or by flash chromatography on silica gel (petroleumether/ethyl acetate).
96 %Chromat.	With ammonia; hydrogen; copper(II) nitrate In N,N-dimethyl-formamide at 160℃; for 10h; Sealed tube;	25 Example 25: Preparation of benzodioxane-6-carbonitrile from 3,4-ethylenedioxyiodobenzene (25) Under a nitrogen atmosphere, copper nitrate (20 mol%, 4.7 mg) and magnets were added to a previously baked 10 mL glass pressure tube. Then, N,N-dimethylformamide (0.5 mL) and 3,4-ethylenedioxyiodobenzene (0.125 mmol, 1.0 equiv., 32.8 mg) were added. The pressure tube was sealed and the air inside the tube was removed and filled with carbon dioxide (5.0 equiv., 15 mL), ammonia (5.0 equiv., 15 mL) and hydrogen (5.0 equiv., 15 mL). After the addition was completed, the glass pressure tube was placed in a metal module that had been preheated to 160° C. and stirred for 10 hours. After the reaction was completed, the reaction system was cooled to room temperature and pressure was slowly released. Using dodecane as an internal standard, the gas chromatographic working curve confirmed that the yield was 96%.

Reference： [1]Wang, Hua; Dong, Yanan; Zheng, Chaonan; Sandoval, Christian A.; Wang, Xue; Makha, Mohamed; Li, Yuehui [Chem, 2018, vol. 4, # 12, p. 2883 - 2893]
[2]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - CN108017557, 2018, A Location in patent: Paragraph 0107-0109

67
[ 57744-67-9 ]
C₂₇H₃₂N₂O₂ [ No CAS ]
C₃₅H₃₈N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With 3,5-bis(trifluoromethyl)-2-hydroxypyridine; silver(I) acetate; palladium diacetate; methyl (1S)-bicyclo<2.2.1>hept-2-eno-2-carboxylate In chloroform Inert atmosphere; Heating; enantioselective reaction;	General procedure for the Pd/(+)-NBE-CO2Me catalysed enantioselective meta-C-H activation General procedure: Arene (0.10 mmol, 1.0 equiv), Pd(OAc)2 (2.2 mg, 10 μmol,10 mol%), ligand (15 mol% or 20 mol%), hydrogen phosphate (15 mol% for benzylamine substrate), aryl iodide (0.3 mmol, 3.0 equiv.) and silver acetate (50 mg, 0.30 mmol, 3.0 equiv.) were added into a 2-dram reaction vial. Solvent and (+)-NBE-CO2Me (20 mol% or 50 mol%) were added to the mixture. The vial was flushed with N2 and capped. The reaction mixture was then stirred at the selected temperature for 12-24 h. After cooling to room temperature, the mixture was filtered through Celite and eluted with ethyl acetate. The filtrate was evaporated under reduced pressure. Purification by preparative thin-layer chromatography afforded the desired product.

Reference： [1]Shi, Hang; Herron, Alastair N.; Shao, Ying; Shao, Qian; Yu, Jin-Quan [Nature, 2018, vol. 558, # 7711, p. 581 - 585]

68
[ 578-66-5 ]
[ 57744-67-9 ]
[ 21436-44-2 ]
2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-methyl-N-(quinolin-8-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With silver(I) acetate; palladium diacetate In neat (no solvent) at 110℃; for 24h; Inert atmosphere;	3.2. General experimental procedure for the multicomponent, solvent-free Pd(II)-catalyzed direct β-C-H arylation of carboxamides involving anhydrides as substrates via in situ installation of DG General procedure: A mixture of anhydride (2,1 equiv), DG (8-aminoquinoline, 3a, 1 equiv), ArI (4-6 equiv), Pd(OAc)2 (10 mol%) and AgOAc (2.2 equiv) was heated at 110 °C for an appropriate time (2-24 h, see the corresponding Tables/Schemes for exact time and other specific conditions). Then, reaction mixture was cooled to rt, filtered on celite (EtOAc was used as a washing solvent) and the filtrate was treated with aq. NaHCO3 solution and then, extracted using EtOAc. The combined organic layers were dried over anhydrous Na2SO4 and evaporated to afford the crude reaction mixture. Then, the crude reaction mixture was subjected to the column chromatographic purification (EtOAc:Hexane 20:80) to give the corresponding C-H arylated product (see the respective Tables/Schemes for the specific entries).

Reference： [1]Dalal, Arup; Singh, Prabhakar; Babu, Srinivasarao Arulananda [Tetrahedron, 2019, vol. 75, # 9, p. 1246 - 1257]

69
[ 106-31-0 ]
[ 578-66-5 ]
[ 57744-67-9 ]
3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-N-(quinolin-8-yl)butanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With silver(I) acetate; palladium diacetate In neat (no solvent) at 110℃; for 24h; Inert atmosphere;	3.2. General experimental procedure for the multicomponent, solvent-free Pd(II)-catalyzed direct β-C-H arylation of carboxamides involving anhydrides as substrates via in situ installation of DG General procedure: A mixture of anhydride (2,1 equiv), DG (8-aminoquinoline, 3a, 1 equiv), ArI (4-6 equiv), Pd(OAc)2 (10 mol%) and AgOAc (2.2 equiv) was heated at 110 °C for an appropriate time (2-24 h, see the corresponding Tables/Schemes for exact time and other specific conditions). Then, reaction mixture was cooled to rt, filtered on celite (EtOAc was used as a washing solvent) and the filtrate was treated with aq. NaHCO3 solution and then, extracted using EtOAc. The combined organic layers were dried over anhydrous Na2SO4 and evaporated to afford the crude reaction mixture. Then, the crude reaction mixture was subjected to the column chromatographic purification (EtOAc:Hexane 20:80) to give the corresponding C-H arylated product (see the respective Tables/Schemes for the specific entries).

Reference： [1]Dalal, Arup; Singh, Prabhakar; Babu, Srinivasarao Arulananda [Tetrahedron, 2019, vol. 75, # 9, p. 1246 - 1257]

70
[ 578-66-5 ]
[ 57744-67-9 ]
[ 2082-59-9 ]
3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-N-(quinolin-8-yl)pentanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With silver(I) acetate; palladium diacetate In neat (no solvent) at 110℃; for 24h; Inert atmosphere;	3.2. General experimental procedure for the multicomponent, solvent-free Pd(II)-catalyzed direct β-C-H arylation of carboxamides involving anhydrides as substrates via in situ installation of DG General procedure: A mixture of anhydride (2,1 equiv), DG (8-aminoquinoline, 3a, 1 equiv), ArI (4-6 equiv), Pd(OAc)2 (10 mol%) and AgOAc (2.2 equiv) was heated at 110 °C for an appropriate time (2-24 h, see the corresponding Tables/Schemes for exact time and other specific conditions). Then, reaction mixture was cooled to rt, filtered on celite (EtOAc was used as a washing solvent) and the filtrate was treated with aq. NaHCO3 solution and then, extracted using EtOAc. The combined organic layers were dried over anhydrous Na2SO4 and evaporated to afford the crude reaction mixture. Then, the crude reaction mixture was subjected to the column chromatographic purification (EtOAc:Hexane 20:80) to give the corresponding C-H arylated product (see the respective Tables/Schemes for the specific entries).

Reference： [1]Dalal, Arup; Singh, Prabhakar; Babu, Srinivasarao Arulananda [Tetrahedron, 2019, vol. 75, # 9, p. 1246 - 1257]

71
[ 908129-33-9 ]
[ 57744-67-9 ]
(S)-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-(1,3-dioxoisoindolin-2-yl)-N-(quinolin-8-yl)propanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66.7%	With silver tetrafluoroborate; palladium diacetate In <i>tert</i>-butyl alcohol at 85℃; for 24h;

Reference： [1]Lei, Meng; Feng, Huayun; Bai, Enhe; Zhou, Hui; Wang, Jia; Qin, Yanru; Zhang, Haoyang; Wang, Xueyuan; Liu, Zhaogang; Hai, Ou; Liu, Jia; Zhu, Yongqiang [Organic and Biomolecular Chemistry, 2019, vol. 17, # 3, p. 683 - 691]

72
[ 57744-67-9 ]
[ 1180819-69-5 ]
3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-4-(1,3-dioxoisoindolin-2-yl)-N-(quinolin-8-yl)butanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With silver(I) acetate; palladium diacetate In toluene at 110℃; for 24h; Inert atmosphere;	3.4. General procedure for the Pd(II)-catalyzed, 8-aminoquinoline aided β-C-H arylation of short/medium/long chain-based unnatural amino acid carboxamides (6) General procedure: A mixture of an appropriate unnatural amino acid carboxamide 6 (0.15-0.2 mmol, 1 equiv), an appropriate aryl iodide (5 equiv), Pd(OAc)2 (10 mol%) and AgOAc (2.5 equiv) in anhydrous toluene (2-3 mL) was heated at 110 °C for 15-24 h under a nitrogen atm or in a sealed tube. After the reaction period, the reaction mixture was concentrated under reduced pressure to afford a crude reaction mixture, which was purified by column chromatography on neutral alumina or silica gel (eluent EtOAc:hexane) to give the corresponding arylated amino acid (see the respective Schemes/Tables for the specific entries). 3.4.7. 3-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-4-(1,3-dioxoisoindolin-2-yl)-N-(quinolin-8-yl)butanamide (8h). The compound 8h was obtained after purification by columnchromatography on silica gel (EtOAc:hexane 40:60) as a colourlesssolid (55 mg, 74%); Rf (40% EtOAc/hexane) 0.3; mp:190e192 C; IR (DCM): 3347, 2929, 1711, 1286, 724 cm1; 1H NMR(400 MHz, CDCl3): dH 9.69 (1H, br. s), 8.79 (1H, dd, J1 4.2,J2 1.5 Hz), 8.46 (1H, dd, J1 7.6, J2 1.2 Hz), 8.10 (1H, dd, J1 8.2,J2 1.5 Hz), 7.64 (2H, dd, J1 5.4, J2 3.0 Hz), 7.54 (2H, dd, J1 5.4,J2 3.1 Hz), 7.43 (1H, dd, J1 8.2, J2 4.2 Hz), 7.39 (1H, dd, J1 8.3,J2 1.3 Hz), 7.33 (1H, t, J 8.0 Hz), 6.93 (1H, d, J 2.0 Hz), 6.70 (1H,dd, J1 8.3, J2 2.1 Hz), 6.80 (1H, d, J 8.2 Hz), 4.19 (4H, s),4.03e3.89 (3H, m), 2.97e2.88 (2H, m); 13C NMR (CDCl3, 101 MHz):dC 169.3, 168.3, 148.1, 143.6, 142.6, 138.1, 136.2, 134.2, 134.1, 133.7,131.8, 127.7, 127.2, 123.1, 121.5, 121.3, 120.7, 117.5, 116.5, 116.2, 64.3,43.4, 42.2, 40.2; HRMS (ESI) calcd for C29H24N3O5 [MH] 494.1716found 494.1696.

Reference： [1]Tomar, Radha; Bhattacharya, Debabrata; Babu, Srinivasarao Arulananda [Tetrahedron, 2019, vol. 75, # 17, p. 2447 - 2465]

73
[ 57744-67-9 ]
5-(1,3-dioxoisoindolin-2-yl)-N-(quinolin-8-yl)pentanamide [ No CAS ]
3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-(1,3-dioxoisoindolin-2-yl)-N-(quinolin-8-yl)pentanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With silver(I) acetate; palladium diacetate In toluene at 110℃; for 24h; Inert atmosphere;	3.4. General procedure for the Pd(II)-catalyzed, 8-aminoquinoline aided β-C-H arylation of short/medium/long chain-based unnatural amino acid carboxamides (6) General procedure: A mixture of an appropriate unnatural amino acid carboxamide 6 (0.15-0.2 mmol, 1 equiv), an appropriate aryl iodide (5 equiv), Pd(OAc)2 (10 mol%) and AgOAc (2.5 equiv) in anhydrous toluene (2-3 mL) was heated at 110 °C for 15-24 h under a nitrogen atm or in a sealed tube. After the reaction period, the reaction mixture was concentrated under reduced pressure to afford a crude reaction mixture, which was purified by column chromatography on neutral alumina or silica gel (eluent EtOAc:hexane) to give the corresponding arylated amino acid (see the respective Schemes/Tables for the specific entries). 3.4.23. 3-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-5-(1,3-dioxoisoindolin-2-yl)-N-(quinolin-8-yl)pentanamide (9d). The compound 9d was obtained after purification by column chromatography on silica gel (EtOAc:hexane 40:60) as a colourlesssolid (54 mg, 71%); Rf (40% EtOAc/hexane) 0.3; mp:142e144 C; IR (DCM): 3055, 2986, 1709, 1265, 743 cm1; 1H NMR(400 MHz, CDCl3): dH 9.65 (1H, br. s), 8.76 (1H, dd, J1 4.4,J2 1.6 Hz), 8.70 (1H, dd, J1 7.2, J2 2.0 Hz), 8.13 (1H, dd, J1 8.2,J2 1.4 Hz), 7.77 (2H, dd, J1 5.6, J2 3.2 Hz), 7.67 (2H, dd, J1 5.4,J2 3.0 Hz), 7.52e7.47 (2H, m), 7.44 (1H, dd, J1 8.2, J2 4.0 Hz),6.83e6.81 (2H, m), 6.73 (1H, d, J 8.0 Hz), 4.16e4.12 (4H, m), 3.67(2H, t, J 7.2 Hz), 3.33e3.28 (1H, m), 2.87e2.77 (2H, m), 2.24e2.12(2H, m); 13C NMR (CDCl3, 101 MHz): dC 169.7, 168.2, 148.0, 143.4,142.2, 138.2, 136.3, 136.0, 134.3, 133.7, 132.1, 127.8, 127.4, 123.0,121.5, 121.4, 120.5, 117.4, 116.5, 116.1, 64.2, 64.2, 46.1, 40.1, 36.6, 33.8;HRMS (ESI) calcd for C30H26N3O5 [MH] 508.1872 found 508.1846.

Reference： [1]Tomar, Radha; Bhattacharya, Debabrata; Babu, Srinivasarao Arulananda [Tetrahedron, 2019, vol. 75, # 17, p. 2447 - 2465]

74
[ 57744-67-9 ]
12-(1,3-dioxoisoindolin-2-yl)-N-(quinolin-8-yl)dodecanamide [ No CAS ]
3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-12-(1,3-dioxoisoindolin-2-yl)-N-(quinolin-8-yl)dodecanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With silver(I) acetate; palladium diacetate In toluene at 110℃; for 24h; Inert atmosphere;	3.4. General procedure for the Pd(II)-catalyzed, 8-aminoquinoline aided β-C-H arylation of short/medium/long chain-based unnatural amino acid carboxamides (6) General procedure: A mixture of an appropriate unnatural amino acid carboxamide 6 (0.15-0.2 mmol, 1 equiv), an appropriate aryl iodide (5 equiv), Pd(OAc)2 (10 mol%) and AgOAc (2.5 equiv) in anhydrous toluene (2-3 mL) was heated at 110 °C for 15-24 h under a nitrogen atm or in a sealed tube. After the reaction period, the reaction mixture was concentrated under reduced pressure to afford a crude reaction mixture, which was purified by column chromatography on neutral alumina or silica gel (eluent EtOAc:hexane) to give the corresponding arylated amino acid (see the respective Schemes/Tables for the specific entries). 3.4.46. 3-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-12-(1,3-dioxoisoindolin-2-yl)-N-(quinolin-8-yl)dodecanamide (14d). The compound 14d was obtained after purification by column chromatography on silica gel (EtOAc:hexane 40:60) as a paleyellow color liquid (64 mg, 70%); Rf (40% EtOAc/hexane) 0.3; IR(DCM): 2928, 1708, 1526, 1286, 720 cm1; 1H NMR (400 MHz,CDCl3) dH 9.68 (1H, br. s), 8.79e8.74 (2H, m), 8.15 (1H, d, J 8.2 Hz),7.85 (2H, dd, J1 5.0, J2 3.0 Hz), 7.71 (2H, dd, J1 4.8, J2 3.0 Hz),7.54e7.49 (2H, m), 7.45 (1H, dd, J1 8.3, J2 4.3 Hz), 6.80e6.78 (3H,m), 4.20 (4H, s), 3.67 (2H, t, J 7.2 Hz), 3.20e3.16 (1H, m), 2.80 (2H,d, J 7.2 Hz), 1.75e1.72 (1H, m), 1.67e1.64 (3H, m), 1.31e1.21 (12H,m); 13C NMR (CDCl3, 101 MHz): dC 170.5, 168.5, 148.0, 143.4, 141.9,138.3, 137.8,136.3, 134.5, 133.8,132.2,127.9,127.4,123.1,121.5,121.3,120.6, 117.2, 116.4, 116.0, 64.3, 64.3, 46.0, 42.0, 38.1, 36.3, 29.5, 29.4,29.1, 29.1, 28.6, 27.4, 26.8; HRMS (ESI) calcd for C37H40N3O5 [MH]606.2968 found 606.2943.

Reference： [1]Tomar, Radha; Bhattacharya, Debabrata; Babu, Srinivasarao Arulananda [Tetrahedron, 2019, vol. 75, # 17, p. 2447 - 2465]

75
[ 57744-67-9 ]
[ 1942-45-6 ]
(Z)‐6‐(5‐iodooct‐4‐en‐4‐yl)‐2,3‐dihydrobenzo[b][1,4]dioxine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 1,2-bis(di(pentafluorophenyl)phosphino)ethane In o-xylene at 150℃; for 12h; Glovebox; Sealed tube; Inert atmosphere; stereoselective reaction;

Reference： [1]Lee, Yong Ho; Morandi, Bill [Angewandte Chemie - International Edition, 2019, vol. 58, # 19, p. 6444 - 6448][Angew. Chem., 2019, vol. 131, # 19, p. 6510 - 6515,6]

76
[ 57744-67-9 ]
tert-butyl (3R)-3-(pyridine-2-amido)piperidine-1-carboxylate [ No CAS ]
tert-butyl (3R,5R)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-5-(pyridine-2-amido)piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With 2,6-dimethylbenzoic acid; palladium diacetate; silver carbonate In <i>tert</i>-butyl alcohol at 120℃; for 24h; Sealed tube; Inert atmosphere;
65.6%	With 2,6-dimethylbenzoic acid; palladium diacetate; silver carbonate In <i>tert</i>-butyl alcohol at 120℃; for 24h; Inert atmosphere; Sealed tube;	18.1 (1) Preparation of Intermediate 2 To a pressure flask (100 mL) equipped with a magnetic stir bar was added Compound Intermediate 1 (2.5 g, 8.19 mmol), silver carbonate (2.26 g, 8.19 mmol), Pd(OAc) 2 (184 mg, 0.82). Millimoles), 6-iodo-2,3-dihydro-1,4-benzodioxin (5.0g, 19.1mmol), 2,6-dimethylbenzoic acid (307mg, 2.05mmol) and 30mL tert Butanol. The container was flushed with argon, sealed with a crimped lid and heated to 120°C. After 24 hours, the reaction vessel was taken out of the oil bath, cooled to room temperature, and dichloromethane (50 mL) was added to the reaction mixture. The mixture was stirred well for 10 minutes, filtered to remove solids, and rinsed with dichloromethane (50 mL). The combined filtrates were concentrated under reduced pressure, and the residue was purified by column chromatography to obtain Intermediate 2.

Reference： [1]Huang, Luyi; Li, Hui; Li, Linli; Niu, Lu; Seupel, Raina; Wu, Chengyong; Cheng, Wei; Chen, Chong; Ding, Bisen; Brennan, Paul E.; Yang, Shengyong [Journal of Medicinal Chemistry, 2019, vol. 62, # 9, p. 4526 - 4542]
[2]Current Patent Assignee: SICHUAN UNIVERSITY - CN111499639, 2020, A Location in patent: Paragraph 0149-0154

77
[ 57744-67-9 ]
[ 40137-29-9 ]
9-chloro-2,3-dihydroanthra[1,2-b][1,4]dioxine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With trifluorormethanesulfonic acid; palladium diacetate; silver trifluoroacetate; acetic acid; glycine; at 100℃; for 24h;Sealed tube;	General procedure: A sealed tube with magnetic stir bar was charged with substrate 1 (0.24 mmol), glycine (0.1 mmol, 7.5 mg), Pd(OAc)2 (0.02 mmol, 4.45 mg), AgTFA (0.24 mmol, 53.01 mg) and 2 (0.2 mmol) under air. After addition of AcOH (2 mL) as solvent, TfOH (0.1 mmol, 15.0 mg) was added. The reaction mixture was allowed to stir at 100 C for 24 hours. Upon completion, the reaction mixture was cooled to room temperature, diluted with DCM, and then extracted with saturated NaHCO3 aqueous solution. The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The crude residue was purified by column chromatography on silica gel using PE as the eluent to afford the desired products.

Reference： [1]Tetrahedron,2019,vol. 75,p. 4031 - 4041

78
[ 110-89-4 ]
[ 57744-67-9 ]
[ 201230-82-2 ]
1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-(piperidin-1-yl)ethane-1,2-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With triethylamine In N,N-dimethyl-formamide at 100℃; for 3h; Inert atmosphere; Autoclave;

Reference： [1]Adamcsik, Bernadett; Nagy, Enikő; Pekker, Péter; Skoda-Földes, Rita; Szabó, Péter; Urbán, Béla [RSC Advances, 2020, vol. 10, # 40, p. 23988 - 23998]

79
[ 91-21-4 ]
[ 57744-67-9 ]
[ 1391634-78-8 ]

Yield	Reaction Conditions	Operation in experiment
51%	With potassium phosphate; copper(l) iodide; ethylene glycol In isopropyl alcohol at 85 - 90℃; for 24h; Schlenk technique; Inert atmosphere;

Reference： [1]Chen, Zhi-Hao; Gao, Pei-Sen; Mei, Tian-Sheng; Sun, Bing; Wang, Zhen-Hua; Weng, Xin-Jun; You, Shu-Li; Zheng, Chao [Angewandte Chemie - International Edition, 2020, vol. 59, # 35, p. 15254 - 15259][Angew. Chem., 2020, vol. 132, # 35, p. 15366 - 15371,6]

80
[ 57744-67-9 ]
C₇H₁₁NO₂ [ No CAS ]
3-(1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)butyl)oxazolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With nickel(II) bromide dimethoxyethane; potassium fluoride; 4,4'-dimethyl-2,2'-bipyridines; diethoxymethylsilane In N,N-dimethyl-formamide at 25℃; for 48h; Inert atmosphere; Sealed tube; regioselective reaction;

Reference： [1]Chen, Yifeng; Huang, Wenyi; Qu, Jingping; Wang, Chenchen; Xi, Yang [Organic Letters, 2020, vol. 22, # 23, p. 9319 - 9324]

81
[ 57744-67-9 ]
[ 42463-41-2 ]
1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(hydroxymethyl)pyridin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With potassium phosphate; copper(l) iodide; N,N-dimethylethylenediamine In 1,4-dioxane at 110℃; Inert atmosphere;	1 Synthesis of 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(hydroxymethyl)pyridin-2(1H)-one To a solution of 3-(hydroxymethyl)pyridin-2(1H)-one (5 g, 39 960 mmol) in 1,4-dioxane (50 mL) was added 6-iodo-2,3-dihydrobenzo[b][1,4]dioxine (12.566 g, 47.952 mmol), Cul (765 mg, 3.996 mmol), K3PO4 (16.964 g, 79.920 mmol) and N,N-dimethylethylenediamine (929 mg, 7.992 mmol) under N2 atmosphere. The resulting mixture was maintained under nitrogen and stirred at 1 10 °C for overnight. After cooling down to rt, the reaction was quenched with water (100 ml_). The resulting mixture was extracted with ethyl acetate (3 x 100 ml_). The organic layers were combined, dried over anhydrous sodium sulfate, the solids were removed by filtration and the filtrate was concentrated under reduced pressure. The crude was purified by silica gel chromatography (0 to 15% CH3OH/ CH2CI2) to afford the titled compound as a white solid (4.4 g, 42%). LC/MS: mass calcd. for CI 4HI3N04: 259.08, found: 260.15 [M+H]+.
42%	With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine In 1,4-dioxane at 110℃; Inert atmosphere;	1 Synthesis of 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(hydroxymethyl)pyridin-2(1H)-one To a solution of 3-(hydroxymethyl)pyridin-2(1H)-one (5 g, 39.960 mmol) in 1,4-dioxane (50 mL) was added 6-iodo-2,3-dihydrobenzo[b][1,4]dioxine (12.566 g, 47.952 mmol), CuI (765 mg, 3.996 mmol), K3PO4 (16.964 g, 79.920 mmol) and N,N’-dimethylethylenediamine (929 mg, 7.992 mmol) under N2 atmosphere. The resulting mixture was maintained under nitrogen and stirred at 110 °C for overnight. After cooling down to rt, the reaction was quenched with water (100 mL). The resulting mixture was extracted with ethyl acetate (3 x 100 mL). The organic layers were combined, dried over anhydrous sodium sulfate, the solids were removed by filtration and the filtrate was concentrated under reduced pressure. The crude was purified by silica gel chromatography (0 to 15% CH3OH/ CH2Cl2) to afford the titled compound as a white solid (4.4 g, 42%). LC/MS: mass calcd. for C14H13NO4: 259.08, found: 260.15 [M+H]+.

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2020/245372, 2020, A1 Location in patent: Page/Page column 35-36
[2]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2020/255020, 2020, A1 Location in patent: Page/Page column 87; 88

82
[ 57744-67-9 ]
[ 124-38-9 ]
[ 536-74-3 ]
[ 1347922-78-4 ]

Yield	Reaction Conditions	Operation in experiment
71%	Stage #1: carbon dioxide With phenylsilane In N,N-dimethyl-formamide at 60℃; for 3h; Schlenk technique; Sealed tube; Stage #2: 6-iodo-1,4-benzodioxane; phenylacetylene With (bis(tricyclohexyl)phosphine)palladium(II) dichloride; triethylamine In N,N-dimethyl-formamide Schlenk technique; Sealed tube;

Reference： [1]Xiong, Wenfang; Wu, Bowen; Zhu, Baiyao; Tan, Xiaobin; Wang, Lu; Wu, Wanqing; Qi, Chaorong; Jiang, Huanfeng [ChemCatChem, 2021, vol. 13, # 12, p. 2843 - 2851]

83
[ 57744-67-9 ]
[ 1173932-08-5 ]
2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-N-(quinolin-8-yl)pyrene-1-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With silver(I) acetate; palladium diacetate In o-xylene at 130℃; for 24h; Inert atmosphere;	Pd(II)-Catalyzed Arylation of Carboxamides 2a/2d and Preparation of Compounds 4/6 General procedure: A mixture of an appropriate carboxamide (0.2 mmol, 1 equiv), an appropriatearyl iodide (0.8 mmol, 4 equiv), Pd(OAc)2 (4.5 mg, 10 mol%)and AgOAc (0.44 mmol, 2.0-2.2 equiv) in o-xylene (2 mL) was heatedat 130 °C for 24 h in a 10 mL capacity sealed (pressure) tube (the pressuretube was flushed with nitrogen atmosphere for 2 min and it wassealed with a PTFE-lined cap, and then the tube was heated). After thereaction period, the reaction mixture was concentrated under vacuumand purification of the resulting reaction mixture by columnchromatography on neutral alumina or silica gel (EtOAc/hexane) furnishedthe corresponding arylated carboxamide.

Reference： [1]Dalal, Arup; Babu, Srinivasarao Arulananda [Synthesis, 2021, vol. 53, # 18, p. 3307 - 3324]

84
[ 57744-67-9 ]
N-(pyren-1-yl)-picolinamide [ No CAS ]
N-(10-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)pyren-1-yl)picolinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With silver(I) acetate; palladium diacetate In o-xylene at 150℃; Inert atmosphere;	Pd(II)-Catalyzed Arylation of the Carboxamide 2b and Preparationof Compounds 5 General procedure: A mixture of carboxamide 2b (0.2 mmol, 1 equiv), an appropriate aryliodide (0.8-1.0 mmol, 4-5 equiv), Pd(OAc)2 (4.5 mg, 10 mol%) andAgOAc (0.44 mmol, 2.2 equiv) in o-xylene (2 mL) was heated at 150 °Cfor 36-48 h in a 10 mL capacity sealed (pressure) tube (the pressuretube was flushed with nitrogen atmosphere for 2 min and it wassealed with a PTFE-lined cap, and then the tube was heated). After thereaction period, the reaction mixture was concentrated under vacuumand purification of the resulting reaction mixture by columnchromatography on silica gel (EtOAc/hexane) furnished the correspondingarylated carboxamide.

Reference： [1]Dalal, Arup; Babu, Srinivasarao Arulananda [Synthesis, 2021, vol. 53, # 18, p. 3307 - 3324]

85
[ 57744-67-9 ]
C₁₂H₁₈N₄OSi [ No CAS ]
C₂₀H₂₄N₄O₃Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	Stage #1: C₁₂H₁₈N₄OSi With 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex In tetrahydrofuran at -20℃; for 2h; Stage #2: 6-iodo-1,4-benzodioxane With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; zinc(II) chloride In tetrahydrofuran

Reference： [1]Bein, Thomas; Bessinger, Derya; Brocklehurst, Cara E.; Karaghiosoff, Konstantin; Knochel, Paul; Lima, Fabio; Rout, Saroj K.; Schwärzer, Kuno [Chemical Science, 2021, vol. 12, # 39, p. 12993 - 13000]

86
[ 57744-67-9 ]
difluoroallyl boronate [ No CAS ]
C₁₁H₁₀F₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; N–phenyl–2–(dicyclohexylphosphino)pyrrole In 1,2-dimethoxyethane at 100℃; for 24h; Sealed tube; Inert atmosphere; regioselective reaction;

Reference： [1]Butcher, Trevor W.; Hartwig, John F.; Sakamoto, Shu; Yang, Jonathan L. [Angewandte Chemie - International Edition, 2021, vol. 60, # 49, p. 25746 - 25752][Angew. Chem., 2021, vol. 133, # 49, p. 25950 - 25956]

87
[ 57744-67-9 ]
[ 20394-07-4 ]
C₃₅H₃₆B₁₀O₉ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	Stage #1: 1-formyl-o-carborane With glycine at 40℃; for 1h; Inert atmosphere; Sealed tube; Stage #2: 6-iodo-1,4-benzodioxane With silver orthophosphate; palladium diacetate; sodium hydrogencarbonate at 80℃; for 24h; Inert atmosphere; Sealed tube;

Reference： [1]Cao, Hou-Ji; Chen, Meng; Lu, Changsheng; Shi, Zhuangzhi; Sun, Fangxiang; Yan, Hong; Zhang, Xiaolei; Zhao, Yue [ACS Catalysis, 2021, vol. 11, # 22, p. 14047 - 14057]

88
[ 57744-67-9 ]
[ 1208-63-5 ]
AMG₉₈₁₀ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With copper (I) iodide; tetrabutylammonium bromide; potassium hydroxide at 110℃; for 10h; Sealed tube; Glovebox; Inert atmosphere;	Experimental procedure: The CuI (0.4 mmol), TBAB (16.5 mmol), KOH (16.5 mmol), 2j (1.68 g), 2j (2.59 g) and a stirring bar were added into a tube sealing (38 mL) in glovebox. After sealed, tube sealing was brought out of the glovebox under nitrogen atmosphere. The reaction was performed at 110 °C for 10 h. After the reaction finished, the tube sealing was cooled to room temperature. After cooling, dichloromethane (30 mL) and water (30 mL) were added and the layers were separated. The aqueous layer was extracted three times with dichloromethane, the combined organic extracts were washed with water (three times) and brine. Then the organic phase was dried with MgSO4 and the solvent was concentrated to afford a yellow solid. The crude product was purified by flash column chromatography on silica gel to afford the desired 4jr as a pale yellow solid (64% yield). 1H NMR (400 MHz, CDCl3) δ 10.06 (s, 1H), 7.60-7.50 (m, 3H), 7.45-7.41 (m, 3H), 7.13-7.10 (m, 1H), 6.83-6.76 (m, 2H), 4.25-4.15 (m, 4H), 1.26 (s, 9H). 13C NMR (100 MHz, CDCl3) δ 163.3, 152.4, 143.0, 139.6, 139.4, 133.1, 132, 127.5, 125.7, 121.4, 116.8, 112.5, 108.4, 64.2, 63.9, 34.4, 30.9. (Ref : 1) Md. A. Ali, P. Saha, T. Punniyamurthy, Synthesis 6 (2010): 908-910; 2) Chem. Eur. J. 20 (2014), 4542-4547).
64%	With copper (I) iodide; tetrabutylammonium bromide; potassium hydroxide at 110℃; for 10h; Sealed tube; Glovebox; Inert atmosphere;	Experimental procedure: The CuI (0.4 mmol), TBAB (16.5 mmol), KOH (16.5 mmol), 2j (1.68 g), 2j (2.59 g) and a stirring bar were added into a tube sealing (38 mL) in glovebox. After sealed, tube sealing was brought out of the glovebox under nitrogen atmosphere. The reaction was performed at 110 °C for 10 h. After the reaction finished, the tube sealing was cooled to room temperature. After cooling, dichloromethane (30 mL) and water (30 mL) were added and the layers were separated. The aqueous layer was extracted three times with dichloromethane, the combined organic extracts were washed with water (three times) and brine. Then the organic phase was dried with MgSO4 and the solvent was concentrated to afford a yellow solid. The crude product was purified by flash column chromatography on silica gel to afford the desired 4jr as a pale yellow solid (64% yield). 1H NMR (400 MHz, CDCl3) δ 10.06 (s, 1H), 7.60-7.50 (m, 3H), 7.45-7.41 (m, 3H), 7.13-7.10 (m, 1H), 6.83-6.76 (m, 2H), 4.25-4.15 (m, 4H), 1.26 (s, 9H). 13C NMR (100 MHz, CDCl3) δ 163.3, 152.4, 143.0, 139.6, 139.4, 133.1, 132, 127.5, 125.7, 121.4, 116.8, 112.5, 108.4, 64.2, 63.9, 34.4, 30.9. (Ref : 1) Md. A. Ali, P. Saha, T. Punniyamurthy, Synthesis 6 (2010): 908-910; 2) Chem. Eur. J. 20 (2014), 4542-4547).

Reference： [1]Huang, Zijun; Jiang, Xiongwei; Lan, Donghui; Li, Yuehui; Pi, Shaofeng; Tan, Zhengde; Tang, Jia; Xie, Tianle; Yi, Bing; Zhang, Minmin [Chinese Chemical Letters, 2022]
[2]Huang, Zijun; Jiang, Xiongwei; Lan, Donghui; Li, Yuehui; Pi, Shaofeng; Tan, Zhengde; Tang, Jia; Xie, Tianle; Yi, Bing; Zhang, Minmin [Chinese Chemical Letters, 2022]

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CAS No. :	57744-67-9	MDL No. :	MFCD00221460
Formula :	C₈H₇IO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HZTMYTXWFHBHDC-UHFFFAOYSA-N
M.W :	262.04	Pubchem ID :	2776176
Synonyms :

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 57744-67-9 ] {[proInfo.proName]}

Quality Control of [ 57744-67-9 ]

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[ 57744-67-9 ] Synthesis Path-Upstream 1~3

[ 57744-67-9 ] Synthesis Path-Downstream 1~88

Related Functional Groups of
[ 57744-67-9 ]

Iodides

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[ 57744-67-9 ]

Benzodioxans

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Disposal

Physical hazards

Health hazards

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Inquiry

[ CAS No. 57744-67-9 ] {[proInfo.proName]}

Quality Control of [ 57744-67-9 ]

Related Doc. of [ 57744-67-9 ]

Product Details of [ 57744-67-9 ]

Safety of [ 57744-67-9 ]

Application In Synthesis of [ 57744-67-9 ]

[ 57744-67-9 ] Synthesis Path-Upstream 1~3

[ 57744-67-9 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 57744-67-9 ]

Iodides

Related Parent Nucleus of [ 57744-67-9 ]

Benzodioxans

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 57744-67-9 ]

Related Parent Nucleus of
[ 57744-67-9 ]