[ CAS No. 214360-49-3 ] {[proInfo.proName]}

Name: 214360-49-3|1-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanone|98%
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SKU: A642468
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Quality Control of [ 214360-49-3 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 214360-49-3 ]

CAS No. :	214360-49-3	MDL No. :	MFCD05863923
Formula :	C₁₄H₁₉BO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CMMASGVZWZQOEY-UHFFFAOYSA-N
M.W :	246.11	Pubchem ID :	2760595
Synonyms :

Safety of [ 214360-49-3 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 214360-49-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 214360-49-3 ]
Downstream synthetic route of [ 214360-49-3 ]

[ 214360-49-3 ] Synthesis Path-Upstream 1~1

1
[ 214360-49-3 ]
[ 121-71-1 ]

Reference： [1] Advanced Synthesis and Catalysis, 2011, vol. 353, # 11-12, p. 2169 - 2173

[ 214360-49-3 ] Synthesis Path-Downstream 1~64

1
[ 138313-22-1 ]
[ 25015-63-8 ]
[ 214360-49-3 ]

Yield	Reaction Conditions	Operation in experiment
55%	With triethylamine In 1,4-dioxane at 100℃; for 4h;

Reference： [1]Murata, Miki; Oyama, Takashi; Watanabe, Shinji; Masuda, Yuzuru [Journal of Organic Chemistry, 2000, vol. 65, # 1, p. 164 - 168]

2
[ 214360-49-3 ]
pinacol 3-(1-chlorovinyl)phenylboronate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With triphenyl phosphite; chlorine; triethylamine In dichloromethane for 2h; Heating;

Reference： [1]Spaggiari, Alberto; Vaccari, Daniele; Davoli, Paolo; Torre, Giovanni; Prati, Fabio [Journal of Organic Chemistry, 2007, vol. 72, # 6, p. 2216 - 2219]

3
[ 214360-49-3 ]
2-(3-(1-bromovinyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With triphenyl phosphite; bromine; triethylamine In dichloromethane for 2h; Heating;
	With triphenyl phosphite; bromine; triethylamine In dichloromethane at -60 - 20℃; for 20h; Inert atmosphere; Reflux;

Reference： [1]Spaggiari, Alberto; Vaccari, Daniele; Davoli, Paolo; Torre, Giovanni; Prati, Fabio [Journal of Organic Chemistry, 2007, vol. 72, # 6, p. 2216 - 2219]
[2]Olivares, Astrid M.; Weix, Daniel J. [Journal of the American Chemical Society, 2018, vol. 140, # 7, p. 2446 - 2449]

4
[ 1011472-03-9 ]
[ 214360-49-3 ]
[ 1011472-04-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In tetrahydrofuran; water at 160℃; for 0.166667h; Microwave irradiation;	to a solution of LG2-73 (30 mg, 0.079 mmol), l-[3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl]-ethanone (29 mg, 0.118 mmol, 1.5 equiv.), and Tetrakis(triphenylphosphine)-palladium(0) (11 mg, 0.0096 mmol) in THF (0.8 ml) was added 0.4 ml of aqueous 1 N K2CO3 solution. The resultant mixture was heated atHOU03:1125151 160 0C under microwave irradiation for 10 min. The mixture was diluted with EtOAc (10 ml), and the organic phase was separated out. After removal of solvent, the residue was subjected to flash column chromatography on silica gel (elution with hexane-EtOAc) to yield LG2-75 as a white foam (35 mg). ESI-MS: m/z 419 (M+l); IH NMR (600 MHz, CDC13): δ 8.18 (IH, s), 8.04 (IH, d, J= 7.8 Hz), 7.99 (IH, s), 7.78 (IH, d, J= 7.8 Hz), 7.70 (IH, s), 7.69 (IH, d, J= 4.8 Hz), 7.66 (IH, t, J= 6.8 Hz), 7.52 (IH, d, J= 4.8 Hz), 7.21 (2H, s), 3.92 (6H, s), 3.85 (3H, s), 2.69 (3H, s); 13C NMR (150.9 MHz, CDC13): δ 197.41, 153.43, 146.73, 138.11, 135.32, 133.93, 133.90, 132.36, 132.15, 132.08, 131.33, 129.74, 129.13, 129.07, 128.61, 128.56, 127.56, 108.95, 97.43, 61.05, 56.17, 26.78

Reference： [1]Current Patent Assignee: THE UNIVERSITY OF TEXAS SYSTEM - WO2008/30795, 2008, A2 Location in patent: Page/Page column 20-21

5
[ 1011472-12-0 ]
[ 214360-49-3 ]
[ 1011472-13-1 ]

Yield	Reaction Conditions	Operation in experiment
48%	With potassium carbonate In tetrahydrofuran; water at 160℃; for 0.166667h; Microwave irradiation;	to a solution of LG2-77 (34 mg, 0.091 mmol), l-[3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl]-ethanone (33 mg, 0.136 mmol, 1.5 equiv.) and Tetrakis(triphenylphosphine)- palladium(O) (10 mg, 0.013 mmol) in THF (1.0 ml) was added 0.5 ml of aqueous 1 N K2CO3 solution. The resultant mixture was heated at 160 0C under microwave irradiation for 10 min. The mixture was diluted with EtOAc, and the organic phase was separated out. After removal of solvent, the residue was subjected to flash column chromatography on silica gel (elution with CH2C12-MeOH) to yield LG2-81 as a pale yellow solid (18 mg, 48%). ESI-MS: m/z 414 (M+l); IH NMR (600 MHz, CDC13): δ 8.16 (IH, s, NH), 8.02 (IH, d, J= 7.8 Hz), 7.97 (IH, s), 7.77 (IH, d, J= 7.8 Hz), 7.73 (2H, d, J= 9.0 Hz), 7.67 (IH, s), 7.65 (2H, d+t), 7.48 (lH,d, J= 6.4 Hz), 6.96 (2H, d, J= 9.0 Hz), 3.87 (4H, t, J= 6.4 Hz), 3.14 (4H, t, J= 6.4 Hz), 2.69 (3H, s); 13C NMR (150.9 MHz, CDC13): δ 197.41, 147.63, 146.97, 138.08, 134.00, 132.33, 131.91, 131.22, 129.68, 129.24, 129.21, 128.48, 127.57, 121.43, 116.66, 108.52, 66.97, 50.00, 26.77.

Reference： [1]Current Patent Assignee: THE UNIVERSITY OF TEXAS SYSTEM - WO2008/30795, 2008, A2 Location in patent: Page/Page column 24

6
[ 121-71-1 ]
[ 214360-49-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 2: 55 percent / Et₃N / PdCl₂(dppf) / dioxane / 4 h / 100 °C
	Multi-step reaction with 2 steps 1: triethylamine / dichloromethane 2: potassium acetate / <i>tert</i>-butyl alcohol / 2 h / 90 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: triethylamine / dichloromethane 2: potassium acetate / <i>tert</i>-butyl alcohol / 2 h / 90 °C / Inert atmosphere

Reference： [1]Murata, Miki; Oyama, Takashi; Watanabe, Shinji; Masuda, Yuzuru [Journal of Organic Chemistry, 2000, vol. 65, # 1, p. 164 - 168]
[2]Chow, Wing Kin; So, Chau Ming; Lau, Chak Po; Kwong, Fuk Yee [Chemistry - A European Journal, 2011, vol. 17, # 25, p. 6913 - 6917]
[3]Chow, Wing Kin; So, Chau Ming; Lau, Chak Po; Kwong, Fuk Yee [Chemistry - A European Journal, 2011, vol. 17, # 25, p. 6913 - 6917]

7
[ 76-09-5 ]
3-acetylphenylboronic acid [ No CAS ]
[ 214360-49-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	In tetrahydrofuran at 40℃;
99%	In tetrahydrofuran at 40℃; Reduced pressure;
93%	In diethyl ether at 20℃; for 13h; Molecular sieve; Inert atmosphere;

76%	In tetrahydrofuran at 40℃;	Synthesis of pinacol boronic esters 2a and 2b To a 50mL round-bottomed flask containing anhydrous THF (30mL) were added the appropriate acetylphenyl boronic acid (5mmol, 820mg) and the pinacol (5mmol, 590mg). This solution was evaporated under reduced pressure at 40°C. The addition (30mL) and evaporation of THF were repeated (usually twice) until TLC analysis indicated complete conversion. The crude product was purified by column chromatography (PE/EtOAc=8:2) to afford the pinacol esters as white solids. Data for organoboron compound 2a: white solid (mp=66.3-67.7°C); 1H NMR (200MHz, CDCl3) δ [ppm]=7.91 (m, 5H); 2.62 (s, 3H); 1.36 (s, 12H). 13C NMR (50MHz, CDCl3) δ [ppm]=198.4, 139.0, 134.9, 127.2, 84.2, 26.7, 24.8. FT-IR (KBr) νmax=2988, 1680, 1359, 1093, 1016, 857, 832, 654, 599cm-1. Data for organoboron compound 2b: white solid (mp=50.7-52.5°C). 1H NMR (200MHz, CDCl3) δ [ppm]=8.36 (s, 1H), 8.06 (dt, J=7.8 and 1.6Hz, 1H), 7.99 (dt, J=7.4 and 1.2Hz, 1H), 7.47 (t, J=7.8Hz, 1H), 2.64 (s, 3H), 1.36 (s, 12H). 13C NMR (50MHz, CDCl3) δ [ppm]=198.3, 139.3, 136.5, 134.7, 130.7, 128.0, 84.1, 26.7, 24.8. FT-IR (KBr) νmax=2978, 1712, 1384, 1144, 979, 851, 668cm-1.
	In diethyl ether at 20℃; Inert atmosphere; Molecular sieve;
	In diethyl ether at 20℃; Molecular sieve;
	With magnesium sulfate In dichloromethane at 20℃; Glovebox; Schlenk technique; Inert atmosphere;

Reference： [1]Andrade, Leandro H.; Barcellos, Thiago [Organic Letters, 2009, vol. 11, # 14, p. 3052 - 3055]
[2]Brondani, Patricia B.; De Gonzalo, Gonzalo; Fraaije, Marco W.; Andrade, Leandro H. [Advanced Synthesis and Catalysis, 2011, vol. 353, # 11-12, p. 2169 - 2173]
[3]Huang, Chung-Yang; Doyle, Abigail G. [Journal of the American Chemical Society, 2015, vol. 137, # 17, p. 5638 - 5641]
[4]Reis, Joel S.; Simon, Robert C.; Kroutil, Wolfgang; Andrade, Leandro H. [Tetrahedron Asymmetry, 2013, vol. 24, # 23, p. 1495 - 1501]
[5]Fier, Patrick S.; Luo, Jingwei; Hartwig, John F. [Journal of the American Chemical Society, 2013, vol. 135, # 7, p. 2552 - 2559]
[6]Hu, Jingyu; Gao, Bing; Li, Lingchun; Ni, Chuanfa; Hu, Jinbo [Organic Letters, 2015, vol. 17, # 12, p. 3086 - 3089]
[7]Demonti, Luca; Mézailles, Nicolas; Nebra, Noel; Saffon-Merceron, Nathalie [Chemistry - A European Journal, 2021, vol. 27, # 62, p. 15396 - 15405]

8
[ 214360-49-3 ]
[ 443777-10-4 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium tetrahydroborate In methanol at 0 - 20℃;

Reference： [1]Andrade, Leandro H.; Barcellos, Thiago [Organic Letters, 2009, vol. 11, # 14, p. 3052 - 3055]

9
[ 591-50-4 ]
[ 214360-49-3 ]
[ 3112-01-4 ]

Yield	Reaction Conditions	Operation in experiment
78%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In N,N-dimethyl acetamide at 90℃; for 11h; Inert atmosphere;
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In N,N-dimethyl-formamide at 90℃; for 12h; Inert atmosphere;

Reference： [1]Huang, Chung-Yang; Doyle, Abigail G. [Journal of the American Chemical Society, 2015, vol. 137, # 17, p. 5638 - 5641]
[2]Mo, Fanyang; Jiang, Yubo; Qiu, Di; Zhang, Yan; Wang, Jianbo [Angewandte Chemie - International Edition, 2010, vol. 49, # 10, p. 1846 - 1849]

10
[ 99-03-6 ]
[ 73183-34-3 ]
[ 214360-49-3 ]

Yield	Reaction Conditions	Operation in experiment
65%	With tert.-butylnitrite; dibenzoyl peroxide In acetonitrile at 20℃; for 2h;
65%	With tert-butyl nitrite; benzoyl peroxide In acetonitrile MeCN, CH3C(O)C6H4NH2 (1 mmol) and tBuONO (1.5 mmol) added to B2pin2 (1 mmol) and benzoyl peroxide (0.02 mmol), mixt. stirred at room temp. for 2h; soln. concd. (under reduced pressure), residue chromd.;
61%	Stage #1: 1-(3-aminophenyl)ethanone With tetrafluoroboric acid; sodium nitrite In water at 0℃; for 1.08333h; Stage #2: bis(pinacol)diborane With triphenylphosphine In acetonitrile at 20℃; for 24h; Inert atmosphere; Schlenk technique;	Typical procedure for the borylation of arenediazonium salts The arylamine (10 mmol) was dissolved in a mixture of 5 mL of distilled water and 3:4 mL of 50% tetrafluoroboric acid. After cooling the reaction mixture to 0 °C in an ice bath, sodium nitrite (0:69 g in 2 mL of distilled water ) was added dropwise within 5 min. The resulting mixture was stirred for 1 h, and the precipitate was collected by filtration and redissolved in the minimum amount of acetone. Diethyl ether was added until precipitation of the arenediazonium tetrafluoroborate, which was filtered, washed several times with diethylether, and dried under vacuum. An arenediazonium salt (1:5 mmol), bis(pinacolato)diborane(1 mmol) and PPh3 (2:0 eq.) were weighed in a 25 LSchlenk round bottom flask under nitrogen atmosphere. Then 3 mL of acetonitrile was added by syringe. The resulting solution was stirred at room temperature. The reaction progress was monitored by GC-MS. After the completion of the reaction,the solution was filtered though a short column of silica gel and the column washed with ethyl acetate. The filtrate was concentrated under reduced pressure to leave a crude product, which was purified by flash column chromatography on silica gel to afford the final products.

Reference： [1]Mo, Fanyang; Jiang, Yubo; Qiu, Di; Zhang, Yan; Wang, Jianbo [Angewandte Chemie - International Edition, 2010, vol. 49, # 10, p. 1846 - 1849]
[2]Mo, Fanyang; Jiang, Yubo; Qiu, Di; Zhang, Yan; Wang, Jianbo [Angewandte Chemie - International Edition, 2010, vol. 49, # 10, p. 1846 - 1849]
[3]Chen, Shuangshuang; Pan, Zhangjin; Wang, Yan [Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2014, vol. 69, # 9-10, p. 982 - 986]

11
[ 96-54-8 ]
[ 214360-49-3 ]
[ 1246213-54-6 ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: N-Methylpyrrole; 1-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethanone With indium(III) tris[bis(trifluoromethanesulfonyl)amide]; magnesium sulfate In 1,4-dioxane at 85℃; for 1h; Inert atmosphere; Stage #2: With triethylsilane In 1,4-dioxane at 85℃; for 3h; Inert atmosphere; regioselective reaction;

Reference： [1]Tsuchimoto, Teruhisa; Igarashi, Motohiro; Aoki, Kazuki [Chemistry - A European Journal, 2010, vol. 16, # 30, p. 8975 - 8979]

12
[ 2142-63-4 ]
[ 73183-34-3 ]
[ 214360-49-3 ]

Yield	Reaction Conditions	Operation in experiment
94%	With C₃₇H₅₁ClFeNPPd; potassium acetate In 1,4-dioxane at 80℃; for 3h; Inert atmosphere;
92.6%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 90℃; Inert atmosphere;	9a Intermediate 9a: 1 -[3-(4,4,5,5-Tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl]ethanone To a solution of 1 -(3-bromophenyl)ethanone (1 .0 g, 5.0 mmol) in 1 ,4-dioxane (5 mL), bis(pinacolato)diboron (1 .53 g, 6.0 mmol) and potassium acetate (0.32 g, 3.3 mmol) was added. The reaction mixture was degasified with nitrogen, then Pd(dppf)012 (0.026 g, 0.02 eq) was added and the reaction mixture was maintained at 90 00 over night. After cooling, the reaction mixture was diluted with water and extracted with ethyl acetate anhydrous Na2SO4 andconcentrated. It was then purified by column chromatography to yield the title product (1.14 g, 92.6%) as a pale yellow oil. 1HNMR: (ODd3, 300MHz) 68.29 (s, 1H), 7.91-8.01 (m, 2H), 7.38-7.43 (t, 1H), 2.57 (5,3H), 1 .29 (5, 1 2H).
86%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane for 6h; Inert atmosphere; Reflux;	1.1 Synthesis of m-BAPAc 3-bromoacetophenone (5.97g, 0.03mol), United boronic acid pinacol ester (11.43g, 0.045mol), potassium acetate (5.88g, 0.06mol), 100ml dioxane; under nitrogen with stirring was added Pd (dppf) Cl2(0.22g, 0.3mmol), after the replacement with nitrogen, the reaction was refluxed for 6 hours; after completion of the reaction, cooled to room temperature, most of the salt was removed by suction, and saturated sodium chloride aqueous extracted with ethyl acetate layers were separated and the organic phase washed with water until neutral after drying over anhydrous sodium sulfate and filtered to give a red brown liquid; the solvent was removed by rotary evaporation, silica gel column, eluent VPetroleum ether: VDichloromethane= 1: 2 PURIFICATION, to give a yellow oil, which was allowed to cool cryogenic white solid, yield 86%.

20.6 g	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate In 1,4-dioxane at 80℃; for 4h; Inert atmosphere;	24.1 step 1:Preparation of 1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanone Under nitrogen protection, 3'-bromoacetophenone (19.9 g, 100.0 mmol) was charged.Benzoic acid pinacol ester(25.4g, 100.0 mmol), AcOK (19.6 g, 200.0 mmol) in 300 mL dioxaneTo the solution, Pd(dppf)Cl2 (3.7 g, 5.0 mmol) was added. The reaction mixture was stirred at 80 ° C for 4 h.The reaction solution was quenched with water, extracted with EA (200 mL×3), and the organic phase was backwashed with saturated brine.Dry anhydrous Na2SO4, evaporate in vacuo and pass column chromatography (PE/EA = 10/1)Purification afforded 20.6 g of the title compound as a white solid
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In tetrahydrofuran at 100℃; for 12h; Glovebox; Sealed tube; Inert atmosphere;
	With bis-triphenylphosphine-palladium(II) chloride; potassium acetate In 1,4-dioxane at 100℃; for 12h; Inert atmosphere;	B. Preparation of substrates: General procedure A General procedure: A 100 mL round bottomed flask was charged with a stir bar, Pd(PPh3)2Cl2 (0.18 g, 5 mol%), B2Pin2 (6.0 mmol, 1.2 equiv), aryl bromides 1S1 (5.0 mmol, 1.0 equiv), AcOK (20 mmol, 4.0 equiv) in 40.0 mL anhydrous 1,4-dioxane. The mixture was degassed with nitrogen and heated at 100 °C for 12 hours. The mixture was diluted with EtOAc, and the organic layer was washed with saline, dried over anhydrous Na2SO4 and filtered. The crude product was then chromatographed on silica gel to afford the desired compound 1S2. A 100 mL round bottom flask with a stir bar was fitted with a rubber septum and flame dried under high vacuum. The flask was purged with argon and charged with Pd(PPh3)4 (0.34 g, 6 mol%), K2CO3 (20.0 mmol, 4.0 equiv), 1-bromo-2-naphthol derivatives (5.0 mmol, 1.0 equiv), 1S2 (6.0 mmol, 1.2 equiv), followed by addition of 50.0 mL deoxygenated 1,4-dioxane and 10.0 mL deoxygenated water. The mixture was stirred at 100 °C until the reaction was judged to be completed by TLC analysis. Water was added and extracted with EtOAc. The organic phase was dried over anhydrous MgSO4 and concentrated under reduced pressure. The residue was then chromatographed on neutral Al2O3 to afford the desired compound 1. 1-bromo-2-naphthol derivatives were prepared according to the literature methods [2].

Reference： [1]Location in patent: experimental part Wang, Lianhui; Li, Jingya; Cui, Xiuling; Wu, Yusheng; Zhu, Zhiwu; Wu, Yangjie [Advanced Synthesis and Catalysis, 2010, vol. 352, # 11-12, p. 2002 - 2010]
[2]Current Patent Assignee: CONNEXIOS LIFE SCIENCES PVT - WO2014/202528, 2014, A1 Location in patent: Page/Page column 70; 71
[3]Current Patent Assignee: VALIANT CO., LTD. - CN104370904, 2016, B Location in patent: Paragraph 0040-0043
[4]Current Patent Assignee: CHENGDU BRILLIANT PHARMACEUTICAL CO LTD - CN108191871, 2018, A Location in patent: Paragraph 0198-0203
[5]Das, Sandip Kumar; Roy, Satyajit; Khatua, Hillol; Chattopadhyay, Buddhadeb [Journal of the American Chemical Society, 2018, vol. 140, # 27, p. 8429 - 8433]
[6]Hao, Jiamao; Ge, Yicong; Yang, Liuqing; Wang, Jing; Luan, Xinjun [Tetrahedron Letters, 2021, vol. 71]

13
[ 99-02-5 ]
[ 73183-34-3 ]
[ 214360-49-3 ]

Yield	Reaction Conditions	Operation in experiment
88%	With C₂₄H₃₉O₂PBF₄^(1-)H⁽¹⁺⁾; potassium acetate; palladium diacetate In 1,4-dioxane at 110℃; for 1h; Inert atmosphere; Schlenk technique;
82%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; rac-3-(tert-butyl)-4-(2,6-dimethoxyphenyl)-2,3-dihydrobenzo[d][1,3]oxaphosphole; potassium acetate In N,N-dimethyl acetamide at 100℃; for 12h; Inert atmosphere;

Reference： [1]Li, Pengbin; Fu, Chunling; Ma, Shengming [Organic and Biomolecular Chemistry, 2014, vol. 12, # 22, p. 3604 - 3610]
[2]Location in patent: scheme or table Tang, Wenjun; Keshipeddy, Santosh; Zhang, Yongda; Wei, Xudong; Savoie, Jolaine; Patel, Nitinchandra D.; Yee, Nathan K.; Senanayake, Chris H. [Organic Letters, 2011, vol. 13, # 6, p. 1366 - 1369]

14
[ 58297-34-0 ]
[ 73183-34-3 ]
[ 214360-49-3 ]

Yield	Reaction Conditions	Operation in experiment
93%	With potassium acetate In <i>tert</i>-butyl alcohol at 90℃; for 2h; Inert atmosphere;

Reference： [1]Chow, Wing Kin; So, Chau Ming; Lau, Chak Po; Kwong, Fuk Yee [Chemistry - A European Journal, 2011, vol. 17, # 25, p. 6913 - 6917]

15
[ 1092513-16-0 ]
[ 73183-34-3 ]
[ 214360-49-3 ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium acetate In <i>tert</i>-butyl alcohol at 90℃; for 2h; Inert atmosphere;

Reference： [1]Chow, Wing Kin; So, Chau Ming; Lau, Chak Po; Kwong, Fuk Yee [Chemistry - A European Journal, 2011, vol. 17, # 25, p. 6913 - 6917]

16
[ 214360-49-3 ]
[ 121-71-1 ]

Yield	Reaction Conditions	Operation in experiment
	With recombinant phenylacetone monooxygenase from Thermobifida fusca; NADPH In dimethyl sulfoxide at 25℃; Tris/HCl buffer; Enzymatic reaction; chemoselective reaction;

Reference： [1]Brondani, Patricia B.; De Gonzalo, Gonzalo; Fraaije, Marco W.; Andrade, Leandro H. [Advanced Synthesis and Catalysis, 2011, vol. 353, # 11-12, p. 2169 - 2173]

17
[ 214360-49-3 ]
[ 108-46-3 ]

Yield	Reaction Conditions	Operation in experiment
	With 4-hydroxyacetophenone monooxygenase from Pseudomonas fluorescens; phosphite dehydrogenase; NADPH In dimethyl sulfoxide at 24℃; Tris/HCl buffer; Enzymatic reaction;
	Multi-step reaction with 2 steps 1: recombinant phenylacetone monooxygenase from Thermobifida fusca; NADPH / dimethyl sulfoxide / 25 °C / pH 9 / Tris/HCl buffer; Enzymatic reaction 2: phosphite dehydrogenase; 4-hydroxyacetophenone monooxygenase from Pseudomonas fluorescens; NADPH / dimethyl sulfoxide / 24 °C / Tris/HCl buffer; Enzymatic reaction

Reference： [1]Brondani, Patricia B.; De Gonzalo, Gonzalo; Fraaije, Marco W.; Andrade, Leandro H. [Advanced Synthesis and Catalysis, 2011, vol. 353, # 11-12, p. 2169 - 2173]
[2]Brondani, Patricia B.; De Gonzalo, Gonzalo; Fraaije, Marco W.; Andrade, Leandro H. [Advanced Synthesis and Catalysis, 2011, vol. 353, # 11-12, p. 2169 - 2173]

18
[ 1012986-07-0 ]
[ 25015-63-8 ]
[ 214360-49-3 ]

Yield	Reaction Conditions	Operation in experiment
76%	With Et₃N; tetrabutylammonium iodide In 1,4-dioxane 100°C, 24 h; GC;
76%	With 1,1'-bis(di-tertbutylphosphino)ferrocene; tetra-(n-butyl)ammonium iodide; triethylamine; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In 1,4-dioxane at 100℃; for 24h; Inert atmosphere;

Reference： [1]Murata, Miki; Oda, Takeshi; Sogabe, Yosuke; Tone, Hirofumi; Namikoshi, Takeshi; Watanabe, Shinji [Chemistry Letters, 2011, vol. 40, # 9, p. 962 - 963]
[2]Murata, Miki; Oda, Takeshi; Sogabe, Yosuke; Tone, Hirofumi; Namikoshi, Takeshi; Watanabe, Shinji [Chemistry Letters, 2011, vol. 40, # 9, p. 962 - 963]

19
[ 214360-49-3 ]
[ 864754-38-1 ]

Yield	Reaction Conditions	Operation in experiment
	With isopropyl alcohol; NADH at 30℃; for 24h; aq. phosphate buffer; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;	4.6. General procedure for the bioreduction of boron-containing ketones 1a-i catalysed by ADH-A and ADH-LB General procedure: To a phosphate buffer solution (50 mM, pH 7.5, 1 mM NADPH in the case of ADH-LB or 1 mM NADH in the case of ADH-A), substrates (50 mM), 2-propanol (100 μL) and ADH-A (150 μL, thermic precipitated) or ADH-LB (300 μL, crude extract) were added leading to a final volume of 1 mL. Samples were incubated for 24 h at 30 °C and 120 rpm.CommentThe reaction was stopped by the addition of diethyl ether (500 μL). The mixture was mixed thoroughly and centrifuged for 5 min at 13,000 rpm. Then the organic layer was separated from the aqueous phase and the procedure was repeated with diethyl ether (400 μL). The combined organic layers were dried (Na2SO4) and the supernatant was transferred into GC-glass-vials for analysis

Reference： [1]Location in patent: experimental part Barcellos, Thiago; Tauber, Katharina; Kroutil, Wolfgang; Andrade, Leandro H. [Tetrahedron Asymmetry, 2011, vol. 22, # 18-19, p. 1772 - 1777]

20
[ 353-83-3 ]
[ 214360-49-3 ]
[ 906067-23-0 ]

Yield	Reaction Conditions	Operation in experiment
54%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; water; cesium fluoride; copper(l) chloride; XPhos In N,N-dimethyl-formamide at 65℃; for 16h; Inert atmosphere;

Reference： [1]Liang, Apeng; Li, Xinjian; Liu, Dongfeng; Li, Jingya; Zou, Dapeng; Wu, Yangjie; Wu, Yusheng [Chemical Communications, 2012, vol. 48, # 66, p. 8273 - 8275]

21
3-acetylbenzenediazonium tetrafluoroborate [ No CAS ]
[ 73183-34-3 ]
[ 214360-49-3 ]

Yield	Reaction Conditions	Operation in experiment
78%	With eosin In acetonitrile at 20℃; Inert atmosphere; Irradiation;

Reference： [1]Yu, Jian; Zhang, Ling; Yana, Guobing [Advanced Synthesis and Catalysis, 2012, vol. 354, # 14-15, p. 2625 - 2628]

22
[ 214360-49-3 ]
[ 455-36-7 ]

Yield	Reaction Conditions	Operation in experiment
76 %Spectr.	With 1-fluoro-2,4,6-trimethylpyridinium hexafluorophosphate; (tBuCN)2Cu*OTf; silver fluoride In tetrahydrofuran at 50℃; for 18h; Inert atmosphere;

Reference： [1]Fier, Patrick S.; Luo, Jingwei; Hartwig, John F. [Journal of the American Chemical Society, 2013, vol. 135, # 7, p. 2552 - 2559]

23
[ 214360-49-3 ]
(R)-1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
> 99 % ee	With Candida boidinii formate dehydrogenase; 2-aminopropanoic acid; alanine dehydrogenase; pyridoxal 5'-phosphate; (R)-Arthrobacter sp. ω-transaminase; ammonium formate; NADP In aq. phosphate buffer; dimethyl sulfoxide at 30℃; for 24h; Enzymatic reaction;	General procedure for the reductive amination using an AlaDH cofactor recycling system General procedure: Lyophilized cells of E. coli containing the corresponding overexpressed ω-transaminase (20mg) were rehydrated in a potassium phosphate buffer (pH 7.0, 100mM) containing PLP (1mM), NAD+ (1mM), glucose (150mM), LDH (90U), GDH (15U), and d- or l-alanine (500mM) at room temperature for 30min. The substrate 2a (25mM, dissolved in 100μL DMSO) was added afterward and the reductive amination carried out at 30°C in an Eppendorf Thermomixer (600rpm) for 24h (horizontal position). After the indicated time, the reaction was stopped by the addition of saturated Na2CO3 (200μL). The residue was extracted with EtOAc (2×500μL). The combined organic layers were dried over MgSO4 and an aliquot withdrawn for GC analysis (Sections 4.8 and 4.9).

Reference： [1]Reis, Joel S.; Simon, Robert C.; Kroutil, Wolfgang; Andrade, Leandro H. [Tetrahedron Asymmetry, 2013, vol. 24, # 23, p. 1495 - 1501]

24
[ 214360-49-3 ]
[ 1260955-16-5 ]

Yield	Reaction Conditions	Operation in experiment
98 % ee	With Candida boidinii formate dehydrogenase; 2-aminopropanoic acid; alanine dehydrogenase; pyridoxal 5'-phosphate; Chromobacterium violaceum ω-transaminase; ammonium formate; NADP In aq. phosphate buffer; dimethyl sulfoxide at 30℃; for 24h; Enzymatic reaction;	General procedure for the reductive amination using an AlaDH cofactor recycling system General procedure: Lyophilized cells of E. coli containing the corresponding overexpressed ω-transaminase (20mg) were rehydrated in a potassium phosphate buffer (pH 7.0, 100mM) containing PLP (1mM), NAD+ (1mM), glucose (150mM), LDH (90U), GDH (15U), and d- or l-alanine (500mM) at room temperature for 30min. The substrate 2a (25mM, dissolved in 100μL DMSO) was added afterward and the reductive amination carried out at 30°C in an Eppendorf Thermomixer (600rpm) for 24h (horizontal position). After the indicated time, the reaction was stopped by the addition of saturated Na2CO3 (200μL). The residue was extracted with EtOAc (2×500μL). The combined organic layers were dried over MgSO4 and an aliquot withdrawn for GC analysis (Sections 4.8 and 4.9).

Reference： [1]Reis, Joel S.; Simon, Robert C.; Kroutil, Wolfgang; Andrade, Leandro H. [Tetrahedron Asymmetry, 2013, vol. 24, # 23, p. 1495 - 1501]

25
[ 214360-49-3 ]
[ 1260955-17-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 2-aminopropanoic acid; pyridoxal 5'-phosphate; NADP; ammonium formate; Candida boidinii formate dehydrogenase; alanine dehydrogenase; (R)-Arthrobacter sp. ω-transaminase / aq. phosphate buffer; dimethyl sulfoxide / 24 h / 30 °C / Enzymatic reaction 2: pyridine / ethyl acetate / 12 h / 30 °C

Reference： [1]Reis, Joel S.; Simon, Robert C.; Kroutil, Wolfgang; Andrade, Leandro H. [Tetrahedron Asymmetry, 2013, vol. 24, # 23, p. 1495 - 1501]

26
[ 214360-49-3 ]
[ 887147-35-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 2-aminopropanoic acid; pyridoxal 5'-phosphate; NADP; ammonium formate; Candida boidinii formate dehydrogenase; alanine dehydrogenase; Chromobacterium violaceum ω-transaminase / aq. phosphate buffer; dimethyl sulfoxide / 24 h / 30 °C / Enzymatic reaction 2: pyridine / ethyl acetate / 12 h / 30 °C

Reference： [1]Reis, Joel S.; Simon, Robert C.; Kroutil, Wolfgang; Andrade, Leandro H. [Tetrahedron Asymmetry, 2013, vol. 24, # 23, p. 1495 - 1501]

27
[ 105-36-2 ]
[ 214360-49-3 ]
[ 14194-05-9 ]

Yield	Reaction Conditions	Operation in experiment
51.28%	Stage #1: 1-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethanone With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium fluoride; N-benzyl-N,N,N-triethylammonium chloride; tris-(o-tolyl)phosphine In tetrahydrofuran Sealed tube; Inert atmosphere; Stage #2: ethyl bromoacetate In tetrahydrofuran at 60℃;	9 Intermediate 9: (3-Acetylphenyl)acetate A 100 mL sealed tube was charged with 1 -[3-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl] ethanone (0.7 g, 2.8 mmol), benzyltriethylammonium chloride (0.065 g,0.29 mmol), potassium fluoride (0.49 g, 8.5 mmol) and tris(o-tolyl)phosphino (0.077 g,0.25 mmol) and THF (5 mL). To the above solution Pd(dppf)012 (0.078 g, 0.1 mmol)with THF(5 mL) was added. The reaction mixture was degasified with nitrogen,before addition of ethyl bromoacetate (0.87 g, 1 .5 eq) and the reaction mixture is thenheated at 60°C over night. After cooling, the reaction mass was partitioned betweenwater and ethyl acetate. The combined organic layer was dried over anhydrous Na2SO4 and concentrated. The product was purified by combiflash to yield the title product (0.3 g, 51 .28%) as pale yellow oil. LCMS: (M+H) =207.1

Reference： [1]Current Patent Assignee: CONNEXIOS LIFE SCIENCES PVT - WO2014/202528, 2014, A1 Location in patent: Page/Page column 71

28
[ 214360-49-3 ]
(3Z)-6-fluoro-5-(2'-hydroxybiphenyl-4-yl)-3-(1-{3-[2-oxo-2-(pyrrolidin-1-yl)ethyl]phenyl}ethylidene)-1,3-dihydro-2H-indol-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tris-(o-tolyl)phosphine; N-benzyl-N,N,N-triethylammonium chloride; potassium fluoride / tetrahydrofuran / Sealed tube; Inert atmosphere 1.2: 60 °C 2.1: ethanol / 80 °C

Reference： [1]Current Patent Assignee: CONNEXIOS LIFE SCIENCES PVT - WO2014/202528, 2014, A1

29
[ 7057-97-8 ]
[ 214360-49-3 ]
1-isopropyl-3-{1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl}-1H-pyrrole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	Stage #1: N-isopropylpyrrole; 1-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethanone With bis(trifluoromethanesulfonyl)amide In 1,4-dioxane at 85℃; for 3h; Schlenk technique; Inert atmosphere; Stage #2: With triethylsilane In 1,4-dioxane at 85℃; for 4h; Schlenk technique; Inert atmosphere; regioselective reaction;

Reference： [1]Nomiyamaa, Shota; Tsuchimotoa, Teruhisa [Advanced Synthesis and Catalysis, 2014, vol. 356, # 18, p. 3881 - 3891]

30
[ 373-53-5 ]
[ 214360-49-3 ]
[ 82026-75-3 ]

Yield	Reaction Conditions	Operation in experiment
59%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; tris-(o-tolyl)phosphine In dichloromethane; water; N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere;

Reference： [1]Hu, Jingyu; Gao, Bing; Li, Lingchun; Ni, Chuanfa; Hu, Jinbo [Organic Letters, 2015, vol. 17, # 12, p. 3086 - 3089]

31
[ 214360-49-3 ]
1-([1,1'-biphenyl]-3-yl)-1-methyl-N-tosylaziridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / N,N-dimethyl acetamide / 11 h / 90 °C / Inert atmosphere 2.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 - 0 °C 2.2: 11 h / -78 - 20 °C / Inert atmosphere 3.1: manganese (II) sulfate monohydrate; N-Bromosuccinimide / dichloromethane / 19 h / 20 °C / Inert atmosphere

Reference： [1]Huang, Chung-Yang; Doyle, Abigail G. [Journal of the American Chemical Society, 2015, vol. 137, # 17, p. 5638 - 5641]

32
[ 214360-49-3 ]
[ 53618-27-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / N,N-dimethyl acetamide / 11 h / 90 °C / Inert atmosphere 2.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 - 0 °C 2.2: 11 h / -78 - 20 °C / Inert atmosphere

Reference： [1]Huang, Chung-Yang; Doyle, Abigail G. [Journal of the American Chemical Society, 2015, vol. 137, # 17, p. 5638 - 5641]

33
[ 5140-72-7 ]
C₁₄H₁₇BNO₅ [ No CAS ]
[ 214360-49-3 ]
1-(3-(6-(4-isobutoxyphenyl)pyridin-2-yl)phenyl)ethan-1-one [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 9976 - 9979
Angew. Chem.,2015,vol. 127,p. 10114 - 10117,4

34
[ 944801-80-3 ]
[ 214360-49-3 ]
C₄₁H₂₈N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene for 6h; Inert atmosphere; Reflux;	1.4 Synthesis of BnImAnPAc BnImAnBr (4.19g, 8mmol) was added to a three-necked flask, m-BAPAc (2.17g, 8.8mmol), aqueous potassium carbonate (15.3g, 0.024mol), 20ml of toluene, 10ml of ethanol; under nitrogen with stirring was added Pd ( PPh3)4(93mg, 0.08mmol), after the replacement with nitrogen, the reaction was refluxed for 6 hours; after completion of the reaction, was cooled to room temperature, the layers were separated and the organic phase washed with saturated sodium chloride until neutral, dried over anhydrous sodium sulfate and filtered to give a brown liquid; spin distilling off the solvent, silica gel column, eluent VPetroleum ether: VChloroform: VEthyl acetate= 5: 2: 1 was purified to obtain the yellow solid was slurried in ethanol to give a pale yellow powder, yield 82%.

Reference： [1]Current Patent Assignee: VALIANT CO., LTD. - CN104370904, 2016, B Location in patent: Paragraph 0040; 0045; 0046

35
[ 944801-80-3 ]
[ 214360-49-3 ]
C₄₇H₃₀N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; toluene; ethanol / 6 h / Inert atmosphere; Reflux 2: sodium methylate / ethanol; tetrahydrofuran / 8 h / Inert atmosphere; Reflux

Reference： [1]Current Patent Assignee: VALIANT CO., LTD. - CN104370904, 2016, B

36
C₃₇H₂₄BrN₃ [ No CAS ]
[ 214360-49-3 ]
C₄₅H₃₁N₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene for 6h; Inert atmosphere; Reflux;	2.5 Synthesis of BnImCzPAc BrBnImCz (4.55g, 7.7mmol) was added to a three-necked flask, m-BAPAc (2.30g, 9.3mmol), aqueous potassium carbonate (15.3g, 0.024mol), 100ml of toluene, 50ml of ethanol; under nitrogen with stirring was added Pd (PPh3)4(89mg, 0.077mmol), after the replacement with nitrogen, the reaction was refluxed for 6 hours; after completion of the reaction, was cooled to room temperature, the layers were separated and the organic phase washed with saturated sodium chloride until neutral, dried over anhydrous sodium sulfate and filtered to give a brown liquid; spin distilling off the solvent, silica gel column, eluent VChloroform: VEthyl acetate= 5: 1 was purified to obtain the white solid in 78% yield.

Reference： [1]Current Patent Assignee: VALIANT CO., LTD. - CN104370904, 2016, B Location in patent: Paragraph 0062; 0074-0076

37
C₃₇H₂₄BrN₃ [ No CAS ]
[ 214360-49-3 ]
C₅₁H₃₃N₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; toluene; ethanol / 6 h / Inert atmosphere; Reflux 2: sodium methylate / ethanol; tetrahydrofuran / 8 h / Inert atmosphere; Reflux

Reference： [1]Current Patent Assignee: VALIANT CO., LTD. - CN104370904, 2016, B

38
[ 474688-73-8 ]
[ 214360-49-3 ]
C₃₂H₂₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 4h;Inert atmosphere; Reflux;	Three necked flask were successively added to 2-NpAnBr (2.1g, 5.5mmol), m-BAPAc (1.49g, 6.05mmol), aqueous potassium carbonate (10g, 0.011mol), 45ml of toluene, 10ml of ethanol; under nitrogen, was added with stirring Pd (PPh3)4(64mg, 0.055mmol), after the replacement with nitrogen, the reaction was refluxed for 4 hours; After completion of the reaction, was cooled to room temperature, the layers were separated and the organic phase washed with saturated sodium chloride until neutral, dried over anhydrous sodium sulfate and filtered to give a brown liquid; spin distilling off the solvent, silica gel column, eluent VPetroleum ether: VDichloromethane= 1: 1 was purified to obtain the white solid was slurried in ethanol to give a white powder, yield 79%.

Reference： [1]Patent: CN104370904,2016,B .Location in patent: Paragraph 0085-0089

39
[ 214360-49-3 ]
C₃₈H₂₄N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; toluene; ethanol / 4 h / Inert atmosphere; Reflux 2: sodium methylate / ethanol; tetrahydrofuran / 8 h / Inert atmosphere; Reflux

Reference： [1]Current Patent Assignee: VALIANT CO., LTD. - CN104370904, 2016, B

40
[ 14452-30-3 ]
[ 73183-34-3 ]
[ 214360-49-3 ]

Yield	Reaction Conditions	Operation in experiment
56 %Chromat.	With pyridine; cesium fluoride In dimethyl sulfoxide at 105℃; for 2h; Inert atmosphere; Schlenk technique;

Reference： [1]Pinet, Sandra; Liautard, Virginie; Debiais, Mégane; Pucheault, Mathieu [Synthesis, 2017, vol. 49, # 21, p. 4759 - 4768]

41
[ 214360-49-3 ]
2-(3-(1-(cyclohex-1-en-1-yl)vinyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triphenyl phosphite; bromine; triethylamine / dichloromethane / 20 h / -60 - 20 °C / Inert atmosphere; Reflux 2: 1,3-bis-(diphenylphosphino)propane; zinc; 5,5′-bis(trifluoromethyl)-2,2′-bipyridine; NiBr2•diglyme; palladium dichloride / N,N-dimethyl-formamide / 12 h / 20 °C

Reference： [1]Olivares, Astrid M.; Weix, Daniel J. [Journal of the American Chemical Society, 2018, vol. 140, # 7, p. 2446 - 2449]

42
[ 214360-49-3 ]
4-(3-(3-acetylphenyl)-8-aminoimidazo[1,5-a]pyrazin-1-yl)-N-(pyridin-2-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane; ethanol / 4 h / 90 °C / Inert atmosphere 2: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane; ethanol / 4 h / 90 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: CHENGDU BRILLIANT PHARMACEUTICAL CO LTD - CN108191871, 2018, A

43
[ 214360-49-3 ]
4-(8-amino-3-(3-(1-hydroxyethyl)phenyl)imidazo[1,5-a]pyrazin-1-yl)-N-(pyridin-2-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane; ethanol / 4 h / 90 °C / Inert atmosphere 2: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane; ethanol / 4 h / 90 °C / Inert atmosphere 3: sodium tetrahydroborate / methanol / 0.5 h / 20 °C

Reference： [1]Current Patent Assignee: CHENGDU BRILLIANT PHARMACEUTICAL CO LTD - CN108191871, 2018, A

44
[ 940307-40-4 ]
[ 214360-49-3 ]
1-(3-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)phenyl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
280 mg	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; ethanol; water at 90℃; for 4h; Inert atmosphere;	24.6 Step 6:1-(3-(8-Amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)-phenyl)ethanonePreparation Under nitrogen, the 1,3-dibromoimidazo[1,5-a]pyrazine-8-amine (292 mg, 1.0 mmol) was charged.1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanone(246 mg, 1.0 mmol) and Na2CO3 (212 mg, 2.0 mmol)In a mixed solution of dioxane/EtOH/water (3 mL/1 mL/1 mL),Pd(dppf)Cl2 (73 mg, 0.1 mmol) was added. The reaction mixture was stirred at 90 ° C for 4 h.After TLC showed that the starting material was completely reacted, water was added to the reaction solution to be quenched, and extracted with EA (5 mL × 3).The organic phase is backwashed with saturated brine and dried over anhydrous Na2SO4.Evaporation in vacuo to obtain a crude solid product, which was obtained by EA/PE (1/2)280 mg of the title compound as a brown solid.

Reference： [1]Current Patent Assignee: CHENGDU BRILLIANT PHARMACEUTICAL CO LTD - CN108191871, 2018, A Location in patent: Paragraph 0200; 0216-0218

45
[ 54230-88-5 ]
[ 214360-49-3 ]
1-(3-(tetrazolo[1,5-a]pyridin-8-yl)phenyl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
260.1 mg	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,2-dimethoxyethane; water at 80℃; for 6h; Inert atmosphere;

Reference： [1]Das, Sandip Kumar; Roy, Satyajit; Khatua, Hillol; Chattopadhyay, Buddhadeb [Journal of the American Chemical Society, 2018, vol. 140, # 27, p. 8429 - 8433]

46
[ 214360-49-3 ]
1-(9H-pyrido[2,3-b]indol-6-yl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / water; 1,2-dimethoxyethane / 6 h / 80 °C / Inert atmosphere 2: bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; silver hexafluoroantimonate / benzene / 24 h / 130 °C / Sealed tube; Glovebox; Inert atmosphere

Reference： [1]Das, Sandip Kumar; Roy, Satyajit; Khatua, Hillol; Chattopadhyay, Buddhadeb [Journal of the American Chemical Society, 2018, vol. 140, # 27, p. 8429 - 8433]

47
[ 214360-49-3 ]
1-(9-(3,4,5-trimethoxybenzyl)-9H-pyrido[2,3-b]indol-6-yl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / water; 1,2-dimethoxyethane / 6 h / 80 °C / Inert atmosphere 2.1: bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; silver hexafluoroantimonate / benzene / 24 h / 130 °C / Sealed tube; Glovebox; Inert atmosphere 2.2: 0.5 h / 70 °C / Sealed tube

Reference： [1]Das, Sandip Kumar; Roy, Satyajit; Khatua, Hillol; Chattopadhyay, Buddhadeb [Journal of the American Chemical Society, 2018, vol. 140, # 27, p. 8429 - 8433]

48
[ 73183-34-3 ]
[ 455-36-7 ]
[ 214360-49-3 ]

Yield	Reaction Conditions	Operation in experiment
60%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; lithium hexamethyldisilazane In toluene at 80℃; for 12h; Inert atmosphere; Schlenk technique;

Reference： [1]Zhao, Xianghu; Wu, Mingsheng; Liu, Yisen; Cao, Song [Organic Letters, 2018, vol. 20, # 18, p. 5564 - 5568]

49
[ 586-42-5 ]
[ 73183-34-3 ]
[ 214360-49-3 ]

Yield	Reaction Conditions	Operation in experiment
87%	With palladium diacetate; 2,2-dimethylpropanoic anhydride; triethylamine; 1,4-di(diphenylphosphino)-butane In 1,4-dioxane at 160℃; for 15h;

Reference： [1]Liu, Chengwei; Ji, Chong-Lei; Hong, Xin; Szostak, Michal [Angewandte Chemie - International Edition, 2018, vol. 57, # 51, p. 16721 - 16726][Angew. Chem., 2018, vol. 130, p. 16963 - 16968,6]

50
[ 98-86-2 ]
[ 73183-34-3 ]
[ 171364-81-1 ]
[ 214360-49-3 ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 7972 - 7979

51
3-bromo-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-8-amine [ No CAS ]
[ 214360-49-3 ]
1-(3-(8-amino-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl)phenyl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66 mg	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,4-dioxane; water at 120℃; for 2h; Inert atmosphere; Sealed tube;	56.1 Step 1. l-(3-(8-amino-6-(trifluoromethyl)imidazo[l,2-a]pyrazin-3-yl)phenyl)ethan-l-one A mixture of 3-bromo-6-(trifluoromethyl)imidazo[l,2-a]pyrazin-8-amine (Example 4, Step 6; 50 mg, 0.18 mmol), l-(3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)ethan- 1-one (88 mg, 0.36 mmol), potassium carbonate (74 mg, 0.53 mmol), and Pd(Ph3P)4 (25 mg, 0.021 mmol) in 1,4-dioxane (2 ml) and water (0.20 ml) was de-gassed and purged with N2 (g) several times prior to heating in a sealed vial at 120 °C for 2 h. Upon cooling to ambient temperature the reaction mixture was diluted with ethyl acetate (15 mL) and filtered through a pad of Celite. The inorganics were thoroughly washed with ethyl aceate and the crude product was purified by CombiFlash chromatography (12 g silica gel column, eluting with 0- 15% methanol/ dichloromethane) to afford the desired product (66 mg, which was treated as 57 mg). LCMS for Ci5H„F3N40 (M+H)+: calculated m/z = 321.3; found 321.1.

Reference： [1]Current Patent Assignee: INCYTE CORP - WO2019/79469, 2019, A1 Location in patent: Page/Page column 203-204

52
[ 38661-81-3 ]
[ 214360-49-3 ]
1-(3-(1-phenylethyl)phenyl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; water; C₂₄H₂₅N₂OP; lithium tert-butoxide In dichloromethane; dimethyl sulfoxide at 20℃; Inert atmosphere; Schlenk technique;

Reference： [1]Jiang, Sheng-Peng; Dong, Xiao-Yang; Gu, Qiang-Shuai; Ye, Liu; Li, Zhong-Liang; Liu, Xin-Yuan [Journal of the American Chemical Society, 2020, vol. 142, # 46, p. 19652 - 19659]

53
[ 214360-49-3 ]
1-(3-(2-hydroxynaphthalen-1-yl)phenyl)ethan-1-one O-methyl oxime [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / 1,4-dioxane; water / 12 h / 100 °C / Inert atmosphere 2: sodium acetate; N,N-dimethyl-formamide / water; ethanol / 2 h / 70 °C / Inert atmosphere

Reference： [1]Hao, Jiamao; Ge, Yicong; Yang, Liuqing; Wang, Jing; Luan, Xinjun [Tetrahedron Letters, 2021, vol. 71]

54
[ 214360-49-3 ]
6-acetyl-2,3-diphenyl-2'H-spiro[indene-1,1'-naphthalen]-2'-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / 1,4-dioxane; water / 12 h / 100 °C / Inert atmosphere 2: potassium carbonate; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; copper diacetate / 1,4-dioxane / 48 h / 90 °C / Inert atmosphere; Sealed tube; Glovebox

Reference： [1]Hao, Jiamao; Ge, Yicong; Yang, Liuqing; Wang, Jing; Luan, Xinjun [Tetrahedron Letters, 2021, vol. 71]

55
[ 214360-49-3 ]
6-(1-(methoxyimino)ethyl)-2,3-diphenyl-2'H-spiro[indene-1,1'-naphthalen]-2'-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / 1,4-dioxane; water / 12 h / 100 °C / Inert atmosphere 2: sodium acetate; N,N-dimethyl-formamide / water; ethanol / 2 h / 70 °C / Inert atmosphere 3: potassium carbonate; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; copper diacetate / 1,4-dioxane / 48 h / 90 °C / Inert atmosphere; Sealed tube; Glovebox

Reference： [1]Hao, Jiamao; Ge, Yicong; Yang, Liuqing; Wang, Jing; Luan, Xinjun [Tetrahedron Letters, 2021, vol. 71]

56
[ 573-97-7 ]
[ 214360-49-3 ]
1-(3-(2-hydroxynaphthalen-1-yl)phenyl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.96 g	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,4-dioxane; water at 100℃; for 12h; Inert atmosphere;	B. Preparation of substrates: General procedure A General procedure: A 100 mL round bottomed flask was charged with a stir bar, Pd(PPh3)2Cl2 (0.18 g, 5 mol%), B2Pin2 (6.0 mmol, 1.2 equiv), aryl bromides 1S1 (5.0 mmol, 1.0 equiv), AcOK (20 mmol, 4.0 equiv) in 40.0 mL anhydrous 1,4-dioxane. The mixture was degassed with nitrogen and heated at 100 °C for 12 hours. The mixture was diluted with EtOAc, and the organic layer was washed with saline, dried over anhydrous Na2SO4 and filtered. The crude product was then chromatographed on silica gel to afford the desired compound 1S2. A 100 mL round bottom flask with a stir bar was fitted with a rubber septum and flame dried under high vacuum. The flask was purged with argon and charged with Pd(PPh3)4 (0.34 g, 6 mol%), K2CO3 (20.0 mmol, 4.0 equiv), 1-bromo-2-naphthol derivatives (5.0 mmol, 1.0 equiv), 1S2 (6.0 mmol, 1.2 equiv), followed by addition of 50.0 mL deoxygenated 1,4-dioxane and 10.0 mL deoxygenated water. The mixture was stirred at 100 °C until the reaction was judged to be completed by TLC analysis. Water was added and extracted with EtOAc. The organic phase was dried over anhydrous MgSO4 and concentrated under reduced pressure. The residue was then chromatographed on neutral Al2O3 to afford the desired compound 1. 1-bromo-2-naphthol derivatives were prepared according to the literature methods [2].

Reference： [1]Hao, Jiamao; Ge, Yicong; Yang, Liuqing; Wang, Jing; Luan, Xinjun [Tetrahedron Letters, 2021, vol. 71]

57
2-(4-(benzyloxy)phenyl)-8-iodo-5,7-dimethoxy-4H-chromen-4-one [ No CAS ]
[ 214360-49-3 ]
C₂₄H₁₈O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-(4-(benzyloxy)phenyl)-8-iodo-5,7-dimethoxy-4H-chromen-4-one; 1-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethanone With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate In water; N,N-dimethyl-formamide at 110℃; Stage #2: With aluminum (III) chloride at 85℃; Stage #3: With boron tribromide at 20℃;

Reference： [1]Li, Jing; Tan, Guishan; Cai, Yabo; Liu, Ruihuan; Xiong, Xiaolin; Gu, Baohua; He, Wei; Liu, Bing; Ren, Qingyun; Wu, Jianping; Chi, Bo; Zhang, Hang; Zhao, Yanzhong; Xu, Yangrui; Zou, Zhenxing; Kang, Fenghua; Xu, Kangping [Biochemical Pharmacology, 2021, vol. 190]

58
C₁₅H₈AgF₉N₂ [ No CAS ]
[ 214360-49-3 ]
[ 349-76-8 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate In acetonitrile at 60℃; for 24h; Inert atmosphere; Darkness; Sealed tube;

Reference： [1]Demonti, Luca; Mézailles, Nicolas; Nebra, Noel; Saffon-Merceron, Nathalie [Chemistry - A European Journal, 2021, vol. 27, # 62, p. 15396 - 15405]

59
[ 214360-49-3 ]
C₂₃H₃₁N₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 12 h / 100 °C 2: methanol; sodium tetrahydroborate / tetrahydrofuran / 2.5 h / 0 - 15 °C / Inert atmosphere