[ CAS No. 4406-77-3 ] {[proInfo.proName]}

Name: 4406-77-3|2-Phenyl-1,3,2-dioxaborinane|98%
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SKU: A572656
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2D 3D

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Quality Control of [ 4406-77-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 4406-77-3 ]

SDS Specification

Alternatived Products of [ 4406-77-3 ]

Product Details of [ 4406-77-3 ]

CAS No. :	4406-77-3	MDL No. :	MFCD00075228
Formula :	C₉H₁₁BO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QLWMDSAMEIJLQB-UHFFFAOYSA-N
M.W :	161.99	Pubchem ID :	642685
Synonyms :

Calculated chemistry of [ 4406-77-3 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	48.42
TPSA :	18.46 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.85 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.03
Log Po/w (WLOGP) :	0.82
Log Po/w (MLOGP) :	0.87
Log Po/w (SILICOS-IT) :	1.16
Consensus Log Po/w :	0.98

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.43
Solubility :	0.606 mg/ml ; 0.00374 mol/l
Class :	Soluble
Log S (Ali) :	-2.05
Solubility :	1.46 mg/ml ; 0.00901 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.74
Solubility :	0.296 mg/ml ; 0.00183 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.69

Safety of [ 4406-77-3 ]

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

Application In Synthesis of [ 4406-77-3 ]

* 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.

Downstream synthetic route of [ 4406-77-3 ]

[ 4406-77-3 ] Synthesis Path-Downstream 1~87

1
[ 504-63-2 ]
[ 98-80-6 ]
[ 4406-77-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	In dichloromethane at 20℃;
76%	In toluene Reflux;
	In ethyl acetate for 0.5h; Ambient temperature; derivatization to boronic acids;

	In toluene Heating;
	In benzene
	In water
	according to M. Pailer and W. Fenzel, Monatsh. Chem., 1961, 92, 1294;
	In dichloromethane at 20℃; Inert atmosphere;
	In dichloromethane at 20℃; Inert atmosphere;

Reference： [1]Dastbaravardeh, Navid; Schnuerch, Michael; Mihovilovic, Marko D. [Organic Letters, 2012, vol. 14, # 7, p. 1930 - 1933]
[2]Meiland, Marcel; Heinze, Thomas; Guenther, Wolfgang; Liebert, Tim [Tetrahedron Letters, 2009, vol. 50, # 4, p. 469 - 472]
[3]Longstaff, Colin; Rose, Malcolm Edward [Organic Mass Spectrometry, 1982, vol. 17, # 10, p. 508 - 518]
[4]Stefaniak,L. et al. [Roczniki Chemii, 1967, vol. 41, # 10, p. 1741 - 1749]
[5]Exner,O.; Bose,R. [Collection of Czechoslovak Chemical Communications, 1974, vol. 39, p. 2234 - 2238]
[6]Davis,F.A. et al. [Journal of Organic Chemistry, 1972, vol. 37, p. 1583 - 1587]
[7]Batrakov; Panosyan; Ushakov; Rozynov; Bergel'son [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1975, vol. 23, # 8, p. 1662 - 1668]
[8]Morgan, Jacqueline; Pinhey, John T. [Journal of the Chemical Society. Perkin transactions I, 1990, p. 715 - 720]
[9]Oda, Susumu; Yamamoto, Hisashi [Angewandte Chemie - International Edition, 2013, vol. 52, # 31, p. 8165 - 8168][Angew. Chem., 2013, vol. 125, # 31, p. 8323 - 8326,4]
[10]Salim Lew, Tedrick Thomas; Wen Lim, Diane Shu; Zhang, Yugen [Green Chemistry, 2015, vol. 17, # 12, p. 5140 - 5143]

2
[ 4406-77-3 ]
[ 696-62-8 ]
[ 613-37-6 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium phosphate In 1,4-dioxane at 115℃; for 30h; Inert atmosphere;
82%	With TlOH In benzene at 50℃; for 15h;
82%	With TlOH In benzene at 50°C, for 15 h;

Reference： [1]Sen, Abhijit; Dhital, Raghu N.; Sato, Takuma; Ohno, Aya; Yamada, Yoichi M.A. [ACS Catalysis, 2020, vol. 10, # 24, p. 14410 - 14418]
[2]Sato, Makoto; Miyaura, Norio; Suzuki, Akira [Chemistry Letters, 1989, p. 1405 - 1408]
[3]Sato, Makoto; Miyaura, Norio; Suzuki, Akira [Chemistry Letters, 1989, p. 1405 - 1408]

3
[ 4406-77-3 ]
[ 175791-62-5 ]
2,4-Dimethyl-5-phenylpyrrolo<2,3-d>pyrimidine [ No CAS ]
2,4-Dimethyl-5-phenyl-7-phenylsulfonylpyrrolo<2,3-d>pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 54% 2: 23%	With potassium phosphate In N,N-dimethyl-formamide at 100℃; for 4h;

Reference： [1]Sakamoto, Takao; Kondo, Yoshinori; Sato, Shuichiroh; Yamanaka, Hiroshi [Journal of the Chemical Society. Perkin transactions I, 1996, # 5, p. 459 - 464]

4
[ 4406-77-3 ]
[ 171288-01-0 ]
[ 171288-08-7 ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium carbonate In tetrahydrofuran at 40℃; for 3h;

Reference： [1]Occhiato, Ernesto G.; Trabocchi, Andrea; Guarna, Antonio [Organic Letters, 2000, vol. 2, # 9, p. 1241 - 1242]

5
[ 4406-77-3 ]
[ 157200-06-1 ]
[ 41398-19-0 ]

Yield	Reaction Conditions	Operation in experiment
84%	With sodium carbonate In 1,2-dimethoxyethane at 65 - 85℃; for 1.25h;

Reference： [1]Aldous; Bower; Moorcroft; Todd [Synlett, 2001, # 1, p. 150 - 152]

6
[ 4406-77-3 ]
[ 1942-45-6 ]
[ 42353-94-6 ]
4-phenyl-5,6-dipropyldeca-(4Z,6E)-4,6-diene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With water In dibutyl ether at 80℃; for 5h; Title compound not separated from byproducts.;

Reference： [1]Shirakawa; Takahashi; Tsuchimoto; Kawakami [Chemical Communications, 2001, # 24, p. 2688 - 2689]

7
[ 4406-77-3 ]
[ 501-65-5 ]
[ 58-72-0 ]

Yield	Reaction Conditions	Operation in experiment
44%	With water In dibutyl ether at 80℃; for 24h;

Reference： [1]Shirakawa; Takahashi; Tsuchimoto; Kawakami [Chemical Communications, 2001, # 24, p. 2688 - 2689]

8
[ 4406-77-3 ]
[ 449187-72-8 ]
6-chloro-2,3-diphenyl-imidazo[2,1-a]phthalazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With sodium hydroxide In 1,2-dimethoxyethane for 8h; Heating;

Reference： [1]Mavel, Sylvie; Thery, Isabelle; Gueiffier, Alain [Archiv der Pharmazie, 2002, vol. 335, # 1, p. 7 - 14]

9
[ 4406-77-3 ]
[ 449187-74-0 ]
2,3-diphenyl-imidazo[2,1-a]phthalazin-6-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With sodium hydroxide In 1,2-dimethoxyethane for 8h; Heating;

Reference： [1]Mavel, Sylvie; Thery, Isabelle; Gueiffier, Alain [Archiv der Pharmazie, 2002, vol. 335, # 1, p. 7 - 14]

10
[ 4406-77-3 ]
[ 449187-73-9 ]
6-chloro-2-(4-fluoro-phenyl)-3-phenyl-imidazo[2,1-a]phthalazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With sodium hydroxide In 1,2-dimethoxyethane for 8h; Heating;

Reference： [1]Mavel, Sylvie; Thery, Isabelle; Gueiffier, Alain [Archiv der Pharmazie, 2002, vol. 335, # 1, p. 7 - 14]

11
[ 4406-77-3 ]
[ 104-88-1 ]
[ 123535-85-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With (S)-1-Ph₂(HO)C-2-(4-t-Bu-4,5-dihydro-oxazol-2-yl)ferrocene; diethylzinc In toluene at 10℃;

Reference： [1]Bolm, Carsten; Rudolph, Jens [Journal of the American Chemical Society, 2002, vol. 124, # 50, p. 14850 - 14851]

12
[ 4406-77-3 ]
[ 92-52-4 ]

Yield	Reaction Conditions	Operation in experiment
91%	With 1,3-bis-(diphenylphosphino)propane; oxygen In dimethyl sulfoxide at 80℃; for 18h;
64%	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; palladium diacetate; tetraethylammonium perchlorate; potassium carbonate In water; acetonitrile at 20℃; Inert atmosphere; Electrochemical reaction;
47%	With iodine; oxygen; potassium carbonate In PEG-400 at 140℃; for 48h;

68 %Spectr.

With palladium diacetate; sodium sulfate; p-benzoquinone In water; N,N-dimethyl-formamide at 80℃; for 0.5h; Electrolysis; Inert atmosphere;

Reference： [1]Yoshida, Hiroto; Yamaryo, Yasuhito; Ohshita, Joji; Kunai, Atsutaka [Tetrahedron Letters, 2003, vol. 44, # 8, p. 1541 - 1544]
[2]Mitsudo, Koichi; Shiraga, Takuya; Kagen, Daisuke; Shi, Deqing; Becker, James Y.; Tanaka, Hideo [Tetrahedron, 2009, vol. 65, # 40, p. 8384 - 8388]
[3]Location in patent: scheme or table Mao, Jincheng; Hua, Qiongqiong; Xie, Guanlei; Yao, Zhigang; Shi, Daqing [European Journal of Organic Chemistry, 2009, # 14, p. 2262 - 2266]
[4]Amatore, Christian; Cammoun, Chama; Jutand, Anny [European Journal of Organic Chemistry, 2008, # 27, p. 4567 - 4570]

13
[ 771-99-3 ]
[ 4406-77-3 ]
[ 220616-20-6 ]

Yield	Reaction Conditions	Operation in experiment
42%	With copper diacetate; triethylamine In dichloromethane at 20℃; for 24h;

Reference： [1]Chan, Dominic M. T.; Monaco, Kevin L.; Li, Renhua; Bonne, Damien; Clark, Charles G.; Lam, Patrick Y. S. [Tetrahedron Letters, 2003, vol. 44, # 19, p. 3863 - 3865]

14
[ 4406-77-3 ]
[ 1138-52-9 ]
[ 62787-21-7 ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 3863 - 3865

15
[ 4406-77-3 ]
[ 10045-45-1 ]
1-ethyl-3-phenyl-1,3-dihydro-2H-benzo[d]imidazol-2-one [ No CAS ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 3863 - 3865

16
[ 541-59-3 ]
[ 4406-77-3 ]
[ 941-69-5 ]

Yield	Reaction Conditions	Operation in experiment
43%	With copper diacetate; oxygen; triethylamine In dichloromethane at 45℃; for 20h;

Reference： [1]Chernick, Erin T.; Ahrens, Michael J.; Scheidt, Karl A.; Wasielewski, Michael R. [Journal of Organic Chemistry, 2005, vol. 70, # 4, p. 1486 - 1489]

17
[ 85-41-6 ]
[ 4406-77-3 ]
[ 520-03-6 ]

Yield	Reaction Conditions	Operation in experiment
97%	With copper diacetate; oxygen; triethylamine In dichloromethane at 45℃; for 20h;

Reference： [1]Chernick, Erin T.; Ahrens, Michael J.; Scheidt, Karl A.; Wasielewski, Michael R. [Journal of Organic Chemistry, 2005, vol. 70, # 4, p. 1486 - 1489]

18
[ 848077-92-9 ]
[ 4406-77-3 ]
5,12-bis(3,5-di-tert-butylphenoxy)-2-octyl-9-phenyl-5a,14c-dihydroanthra[2,1,9-def;6,5,10-d'e'f']diisoquinoline-1,3,8,10-tetraone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With copper diacetate; oxygen; triethylamine In chloroform at 40℃; for 48h;

Reference： [1]Chernick, Erin T.; Ahrens, Michael J.; Scheidt, Karl A.; Wasielewski, Michael R. [Journal of Organic Chemistry, 2005, vol. 70, # 4, p. 1486 - 1489]

19
[ 4406-77-3 ]
[ 81-83-4 ]
[ 6914-98-3 ]

Yield	Reaction Conditions	Operation in experiment
70%	With copper diacetate; oxygen; triethylamine at 55℃;

Reference： [1]Chernick, Erin T.; Ahrens, Michael J.; Scheidt, Karl A.; Wasielewski, Michael R. [Journal of Organic Chemistry, 2005, vol. 70, # 4, p. 1486 - 1489]

20
[ 4406-77-3 ]
[ 122382-54-1 ]
[ 223785-68-0 ]

Yield	Reaction Conditions	Operation in experiment
62%	With 3,3-dimethyl-butan-2-one; carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II) for 1h; Heating;

Reference： [1]Kakiuchi, Fumitoshi; Matsuura, Yusuke; Kan, Shintaro; Chatani, Naoto [Journal of the American Chemical Society, 2005, vol. 127, # 16, p. 5936 - 5945]

21
[ 903586-98-1 ]
[ 4406-77-3 ]
[ 3972-65-4 ]
[ 317802-08-7 ]
polymer, M_w: 10500, polydispersity: 2.04; monomer(s): 3,6-dibromo-9-(4-(3,6-di-tert-butyl-9H-carbazol-9-yl)biphenyl)-9H-carbazole; 9,9-di-n-ocylfluorene-2,7-dioxapropyleneboronate; 1-bromo-4-tert-butylbenzene; 2-phenyl-1,3,2-dioxaborinane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3,6-dibromo-9-(4-(3,6-di-tert-butyl-9H-carbazol-9-yl)biphenyl)-9H-carbazole; 2,7-bis(1,3,2-dioxaborinan-2-yl)-9,9-dioctylfluorene With tetrakis(triphenylphosphine) palladium⁽⁰⁾; Aliquat 336; potassium carbonate In water; toluene at 85℃; for 120h; Stage #2: 2-Phenyl-1,3,2-dioxaborinane In toluene for 24h; Stage #3: 1-bromo-4-tert-butylbenzene In toluene for 24h;

Reference： [1]Chen, Yen-Chun; Huang, Guo-Sheng; Hsiao, Chung-Chin; Chen, Show-An [Journal of the American Chemical Society, 2006, vol. 128, # 26, p. 8549 - 8558]

22
[ 807618-43-5 ]
[ 4406-77-3 ]
[ 3972-65-4 ]
[ 175361-81-6 ]
polymer, alternating, M_n 3700 Da, PDI 1.03; monomer(s): 2,7-dibromo-9,9-di[2-(2-tetrahydropyranyloxy)ethyl]fluorene; 2,2-thiene-2,5-diylbis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane); (trimethylenedioxyboranyl)benzene; 1-bromo-4-tert-butylbenzene [ No CAS ]

Reference： [1]Macromolecules,2005,vol. 38,p. 1114 - 1122

23
[ 4406-77-3 ]
[ 930-30-3 ]
[ 64145-51-3 ]

Yield	Reaction Conditions	Operation in experiment
25%	With (S)-4-methoxy-1,4-diphenyl-1-butyne; water In 1,4-dioxane at 60℃; for 24h;

Reference： [1]Shirakawa, Eiji; Yasuhara, Yuichi; Hayashi, Tamio [Chemistry Letters, 2006, vol. 35, # 7, p. 768 - 769]

24
[ 4406-77-3 ]
[ 18402-83-0 ]
[ 155816-67-4 ]

Yield	Reaction Conditions	Operation in experiment
53%	With water; diphenyl acetylene In 1,4-dioxane at 60℃; for 24h;

Reference： [1]Shirakawa, Eiji; Yasuhara, Yuichi; Hayashi, Tamio [Chemistry Letters, 2006, vol. 35, # 7, p. 768 - 769]

25
[ 4406-77-3 ]
[ 20971-19-1 ]
[ 55830-03-0 ]

Yield	Reaction Conditions	Operation in experiment
34%	With water; diphenyl acetylene In 1,4-dioxane at 60℃; for 24h;

Reference： [1]Shirakawa, Eiji; Yasuhara, Yuichi; Hayashi, Tamio [Chemistry Letters, 2006, vol. 35, # 7, p. 768 - 769]

26
[ 807618-43-5 ]
[ 4406-77-3 ]
[ 3972-65-4 ]
[ 250597-29-6 ]
polymer, alternating, M_n 23800 Da, PDI 2.02; monomer(s): 2,7-dibromo-9,9-di[2-(2-tetrahydropyranyloxy)ethyl]fluorene; 9,9-dihexyl-2,7-(trimethylenedioxyboranyl)fluorene; (trimethylenedioxyboranyl)benzene; 1-bromo-4-tert-butylbenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89.7%	Stage #1: 2,2'-[(2,7-dibromo-9H-fluorene-9,9-diyl)bis(ethane-2,1-diyl)]bis(oxy)}bis(tetrahydro-2H-pyran); 9,9-dihexylfluorene-2,7-bis(trimethylene boronate) With potassium carbonate In tetrahydrofuran at 60℃; for 144h; Stage #2: 2-Phenyl-1,3,2-dioxaborinane With potassium carbonate In tetrahydrofuran for 24h; Stage #3: 1-bromo-4-tert-butylbenzene With potassium carbonate In tetrahydrofuran for 24h;

Reference： [1]Han, Xu; Chen, Xiwen; Vamvounis, George; Holdcroft, Steven [Macromolecules, 2005, vol. 38, # 4, p. 1114 - 1122]

27
[ 4406-77-3 ]
[ 433711-10-5 ]
4,9-diphenyl-non-8-yn-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27%	With water In 1,4-dioxane at 12℃; for 24h;

Reference： [1]Shirakawa, Eiji; Yasuhara, Yuichi; Hayashi, Tamio [Chemistry Letters, 2006, vol. 35, # 7, p. 768 - 769]

28
[ 4406-77-3 ]
[ 78-94-4 ]
[ 2550-26-7 ]

Yield	Reaction Conditions	Operation in experiment
65%	With water; diphenyl acetylene In 1,4-dioxane at 60℃; for 24h;

Reference： [1]Shirakawa, Eiji; Yasuhara, Yuichi; Hayashi, Tamio [Chemistry Letters, 2006, vol. 35, # 7, p. 768 - 769]

29
[ 4406-77-3 ]
[ 140-88-5 ]
[ 2021-28-5 ]

Yield	Reaction Conditions	Operation in experiment
67%	With water; diphenyl acetylene In 1,4-dioxane at 80℃; for 24h;

Reference： [1]Shirakawa, Eiji; Yasuhara, Yuichi; Hayashi, Tamio [Chemistry Letters, 2006, vol. 35, # 7, p. 768 - 769]

30
2-methyl-propane-2-sulfinic acid [(7-bromo-5-nitro-benzofuran-2-yl)-(4-cyano-phenyl)-(3-methyl-3H-imidazol-4-yl)-methyl]-amide [ No CAS ]
[ 4406-77-3 ]
2-methyl-propane-2-sulfinic acid [(4-cyano-phenyl)-(3-methyl-3H-imidazol-4-yl)-(5-nitro-7-phenyl-benzofuran-2-yl)-methyl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate In tetrahydrofuran for 4h; Heating / reflux;	1.1-d 1-d) Preparation of 2-methyl-propane-2-sulfinic acid [(4-cyano-phenyl)-(3-methyl-3H-imidazol-4-yl)-(5-nitro-7-phenyl-benzofuran-2-yl)-methyl] -amide, 8 A mixture 2-methyl-propane-2-sulfinic acid [ (7-BROMO-5- NITRO-BENZOFURAN-2-YL)- (4-CYANO-PHENYL)- (3-METHYL-3H- imidazol-4-yl) -methyl] -amide (1.95 g, 3.50 mmol), 2-phenyl- [1, 3,2] dioxaborinane (1.70 g, 10.5 mmol), tetrakis (triphenylphosphine)-palladium (0) (1.21 g, 1.05 mmol) and tripotassium phosphate (2.23 g, 10.5 mmo) in THF (50 ml) was heated to reflux for 4 hours. The reaction mixture was diluted with AcOEt and then palladium was filtered off. The filtrate was washed with brine, dried over NA2SO4 and evaporated in vacuo. The residue was purified by column chromatography over silica gel (eluent; AcOEt-> 5 % MEOH in AcOEt-> 10 % MeOH in AcOEt), yielding 1.38 g of 2-methyl-propane-2-sulfinic acid [ (4-CYANO- PHENYL)- (3-METHYL-3H-IMIDAZOL-4-YL)- (5-NITRO-7-PHENYL- benzofuran-2-yl) -methyl] -amide as a light yellow amorphous powder. LCMS (condition B), m/z 554 [M+H] +, retention time 3.17 MINUTES 1H-NMR (CDCl3) δ 8.46 (1H, d, J=2.3 Hz), 8.37 (1H, d, J=2.3 Hz), 7.72 (2H, dd, J=2.0, 6.6 Hz), 7.62-7. 66 (2H, m), 7.59 (2H, dd, J=2.0, 8.8 Hz), 7.53 (1H, s), 7.43-7. 51 (3H, m), 7.29 (1H, s), 6.90 (1H, s), 4.64 (1H, s), 3.14 (3H, s), 1.31 (9H, s).

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG; Chugai Pharmaceutical (in: Roche) - WO2004/37816, 2004, A1 Location in patent: Page 32-33

31
2-methyl-propane-2-sulfinic acid [(7-bromo-5-cyano-benzofuran-2-yl)-(4-cyano-phenyl)-(3-methyl-3H-imidazol-4-yl)-methyl]-amide [ No CAS ]
[ 4406-77-3 ]
2-methyl-propane-2-sulfinic acid [(4-cyano-phenyl)-(5-cyano-7-phenyl-benzofuran-2-yl)-(3-methyl-3H-imidazol-4-yl)-methyl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate In DMF (N,N-dimethyl-formamide) at 100℃; for 1h; Heating / reflux;	13.13-e 13-e) Preparation of 2-methyl-propane-2-sulfinic acid [(4-cyano-phenyl)-(5-cyano-7-phenyl-benzofuran-2-yl)- (3-methyl-3H-imidazol-4-yl)-methyl]-amide A mixture of 2-methyl-propane-2-sulfinic acid [ (7-BROMO-5-CYANO-BENZOFURAN-2-YL.)- (4-CYANO-PHENYL)- (3-METHYL-3H-imidazol-4-yl) -methyl] -amide (800 mg, 1.49 mmol), 2- PHENYL-1, 3,2-dioxabororinane (0.67 ml, 4.47 mmol), tetrakis (triphenyl-phosphine)-palladium (0) (345 mg, 0.30 mmol) and tripotassium phosphate (1.27 mg, 5.98 mmo) in DMF (24 ml) was heated at 100 °C for 1 hour. The reaction mixture was diluted with AcOEt and then palladium was filtered off. The filtrate was extracted with AcOEt. The organic layers were combined, washed with brine, dried over NA2SO4 and evaporated in vacuo. The residue was purified by column chromatography over silica gel (eluent; 1 % MEOH in DCM-> 10 % MEOH in DCM), yielding 714 mg of 2-methyl- propane-2-sulfinic acid [ (4-CYANO-PHENYL)- (5-CYANO-7- PHENYL-BENZOFURAN-2-YL)- (3-METHYL-3H-IMIDAZOL-4-YL)- methyl] -amide as a colourless powder. LCMS (condition B) m/z 534 [M+H] +, retention time 3.01 minutes ; 1H-NMR (CDCl3) δ 7.86 (1H, d, J=1.5 Hz), 7.71 (2H, d, J=8.5 Hz), 7.67 (1H, d, J=1.5 Hz), 7.57 (2H, d, J=8.5 Hz), 7. 58-7. 53 (3H, m), 7. 46-7. 42 (3H, m), 7.20 (1H, s), 6.87 (1H, br-s), 4.68 (1H, s), 3.13 (3H, s), 1.30 (9H, s).

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG; Chugai Pharmaceutical (in: Roche) - WO2004/37816, 2004, A1 Location in patent: Page 41-42

32
[ 4406-77-3 ]
[ 98-80-6 ]
[ 725251-90-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate In 1-methyl-pyrrolidin-2-one at 80℃; for 2h;	28 Examples 19 to 36 Examples 19 to 36 The process of Example 1 is repeated in a similar manner except that 0.40 mmol of boron compound as listed in Table 3 is used in place of p-methoxyphenylboronic acid and that 0.30 mmol of the organic halide compound as shown in Table 3 is used in place of 1-bromooctane, and each solvent as shown in Table 3 is used in place of N,N-dimethylacetamide, thereby the desired compounds as listed in Table 3 are obtained.

Reference： [1]Current Patent Assignee: Sumitomo Chemical (w/o Dongwoo Fine-Chem); SUMITOMO CHEMICAL COMPANY LIMITED - EP1439157, 2004, A2 Location in patent: Page 12-16

33
[ 4406-77-3 ]
C₁₂H₂₃Br [ No CAS ]
[ 725251-90-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate In tetrahydrofuran at 80℃; for 2h;	27 Examples 19 to 36 Examples 19 to 36 The process of Example 1 is repeated in a similar manner except that 0.40 mmol of boron compound as listed in Table 3 is used in place of p-methoxyphenylboronic acid and that 0.30 mmol of the organic halide compound as shown in Table 3 is used in place of 1-bromooctane, and each solvent as shown in Table 3 is used in place of N,N-dimethylacetamide, thereby the desired compounds as listed in Table 3 are obtained.

Reference： [1]Current Patent Assignee: Sumitomo Chemical (w/o Dongwoo Fine-Chem); SUMITOMO CHEMICAL COMPANY LIMITED - EP1439157, 2004, A2 Location in patent: Page 12-16

34
[ 4406-77-3 ]
[ 787575-92-2 ]
[ 787575-99-9 ]

Yield	Reaction Conditions	Operation in experiment
97%	With sodium carbonate In methanol; 1,2-dimethoxyethane at 80℃;	117 A mixture of 7-bromo-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide carbarnic acid t-butyl ester (1.50 g, 3.49 mmol), 2-phenyl-1, 3,2-dioxaborinane (1.129 g, 6.98 mmol), Pd (dppb) Cl2 (211 mg, 0.0349 mmol) and Na2C03 (2. 0M, 12 mL) in ethylene glycol dimethyl ether (60 mL) and CH30H (15 mL) is heated to 80 °C (oil bath) with stirring overnight. After cooling to room temperature, the mixture is diluted with EtOAc, filtered and concentrated. The residue is dissolved in EtOAc, washed with brine and dried over Na2S04. The crude material is chromatographed on silica gel (gradient 50% EtOAc in hexane) to give 1.45 g (97% yield) 7-phenyl-isoquinoline-5-sulfonic acid (2- amino-ethyl)-amide carbamic acid t-butyl ester.

Reference： [1]Current Patent Assignee: ELI LILLY & CO - WO2005/54202, 2005, A1 Location in patent: Page/Page column 47

35
[ 857379-53-4 ]
[ 4406-77-3 ]
2-[2-(2-amino-4-methylpyridin-6-yl)ethyl]-6-phenyl-3H-imidazo[4,5-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate In 1,4-dioxane; water at 110℃; for 46h; Heating / reflux;	5 350 mg of 2- [2- (amino-4-methylpyridin-6-yl) ethyl]-6-bromo-3H-imidazo [4,5-b] pyridine (compound 4) are dissolved in 5.6 ml of anoxic dioxane under a nitrogen atmosphere. Subsequently, 3.15 ml of an aqueous sodium bicarbonate solution (2.0 M), 193 mg of 2-phenyl-1, 3,2-dioxaborinane, and 49 mg of trans- dichloro-bis (tricyclohexylphosphane) palladium- (Il) are added. The reaction mixture is refluxed at 110'0 for 46 hours. Thereafter, the volatile components are removed in vacuo and the remaining residue is redissolved in 200 ml of a mixture of water/dichloromethane (1: 1). The aqueous phase is extracted twice each with 125 ml of dichloromethane. The organic layer is separated, dried using sodium sulfate, and evaporated to dryness to yield a colorless, crude solid. Subsequently, the residue is purified by flash chromatography on silica gel (eluent : dichloromethane/methanol 8: 1) to afford 279 mg of the title compound as a colorless solid of m. p. 230°C. MS: 330.3 (MH). TLC: Rf = 0.34 (dichloromethane/methanol 8: 1).

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2005/61496, 2005, A1 Location in patent: Page/Page column 28

36
[ 4406-77-3 ]
[ 460-00-4 ]
[ 324-74-3 ]

Yield	Reaction Conditions	Operation in experiment
94%	With potassium carbonate;Co0.38Fe0.57LaO3Pd0.05; In water; isopropyl alcohol; at 80℃; for 3h;Product distribution / selectivity;	2-4) Reaction between arylbromide and boronic ester The arylbromide and boronic ester shown in TABLE 8 were allowed to react with each other under the reaction conditions shown in TABLE 8, using the Pd-containing perovskite-like composite oxide produced in Example of production 1 as the catalyst for synthesis reaction. Yields in the respective reactions are shown in TABLE 8.

Reference： [1]Patent: US2005/215804,2005,A1 .Location in patent: Page/Page column 16-17

37
[ 104-92-7 ]
[ 4406-77-3 ]
[ 613-37-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With palladium on silica; potassium hydroxide In water for 0.116667h; Microwave irradiation; Green chemistry;
87%	With potassium carbonate In water; isopropyl alcohol at 80℃;	2.4.32 2-4) Reaction between arylbromide and boronic ester The arylbromide and boronic ester shown in TABLE 8 were allowed to react with each other under the reaction conditions shown in TABLE 8, using the Pd-containing perovskite-like composite oxide produced in Example of production 1 as the catalyst for synthesis reaction. Yields in the respective reactions are shown in TABLE 8.

Reference： [1]Kotadia, Deepali A.; Patel, Urmila H.; Gandhi, Sahaj; Soni, Saurabh S. [RSC Advances, 2014, vol. 4, # 62, p. 32826 - 32833]
[2]Current Patent Assignee: UNIVERSITY OF CAMBRIDGE; TOYOTA MOTOR CORPORATION - US2005/215804, 2005, A1 Location in patent: Page/Page column 16-17

38
[ 4406-77-3 ]
[ 352-34-1 ]
[ 324-74-3 ]

Yield	Reaction Conditions	Operation in experiment
94%	With potassium carbonate;Co0.38Fe0.57LaO3Pd0.05; In water; isopropyl alcohol; at 80℃; for 2h;Product distribution / selectivity;	2-5) Reaction between aryliodide and boronic ester The aryliodide and boronic ester shown in TABLE 9 were allowed to react with each other under the reaction conditions shown in TABLE 9, using the Pd-containing perovskite-like composite oxide produced in Example of production 1 as the catalyst for synthesis reaction. Yields in the respective reactions are shown in TABLE 9.

Reference： [1]Patent: US2005/215804,2005,A1 .Location in patent: Page/Page column 18

39
[ 4406-77-3 ]
[ 911199-62-7 ]
[ 911199-52-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate In 1,4-dioxane; water at 110℃; for 96h;	B.1 100 mg of 7-[2-(6-bromo-3H-imidazo[4,5-b]pyridin-2-yl)-ethyl]-azepan-2-one (compound C1) are dissolved in 8.0 ml of oxygen free dioxane under an atmosphere of nitrogen. Subsequently, 900 μl of aqueous sodium carbonate solution (strength 2.0 M), 72 mg of commercially available 2-phenyl-1 ,3,2- dioxoborinane, and 26 mg of frans-dichloro-bis(tricyclohexyl-phosphine)-palladium(ll) are added. The reaction mixture is stirred at 1100C for 96 hours. Thereafter, the mixture is evaporated to dryness and purified by chromatography on basic aluminum oxide (eluent: dichloromethane) to yield 95 mg of the EPO title compound as a light yellow oil. ESI-MS: 335.3 (MH+). TLC: Rf = 0.24 (dichloromethane/ethanol 10:1 parts by volume)

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2006/103255, 2006, A1 Location in patent: Page/Page column 30; 31

40
[ 4406-77-3 ]
[ 927388-42-9 ]
[ 927388-43-0 ]

Yield	Reaction Conditions	Operation in experiment
44%	With potassium phosphate In N,N-dimethyl-formamide at 100℃; for 1h;

Reference： [1]Current Patent Assignee: DAIICHI SANKYO COMPANY, LIMITED - WO2007/20936, 2007, A1 Location in patent: Page/Page column 43

41
[ 4406-77-3 ]
[ 927388-78-1 ]
[ 927388-80-5 ]

Yield	Reaction Conditions	Operation in experiment
84%	With potassium phosphate In N,N-dimethyl-formamide at 95℃;

Reference： [1]Current Patent Assignee: DAIICHI SANKYO COMPANY, LIMITED - WO2007/20936, 2007, A1 Location in patent: Page/Page column 64-65

42
[ 4406-77-3 ]
[ 107-05-1 ]
[ 132350-06-2 ]

Yield	Reaction Conditions	Operation in experiment
70%	With lithium diisopropyl amide In tetrahydrofuran under N2; soln. of B-compd. cooled to -78°C, addn. of allyl chloride and dropwise a soln. of Li-compd., stirred for 0.25 h, warmed to room temp., stirred for 18h; evapd. (vac.), extd. (n-pentane), evapd.; monitored by 11B-NMR;

Reference： [1]Brown, Herbert C.; Rangaishenvi, Milind V.; Jayaraman, Seetharaman [Organometallics, 1992, vol. 11, # 5, p. 1948 - 1954]

43
[ 4406-77-3 ]
[ 917-54-4 ]
[ 97782-78-0 ]

Yield	Reaction Conditions	Operation in experiment
97%	With hydrogenchloride In diethyl ether byproducts: LiCl; 2 equiv of MeLi slowly adding to a soln. of the boronic ester at -78°C, stirring for 3 h at the same temp., 1 equiv of anhydrous HCl in Et2O adding, warming to room temp., stirring for 15 min; the content was detd. by (11)B NMR spectrum;

Reference： [1]Brown, Herbert C.; Cole, Thomas E.; Srebnik, Morris [Organometallics, 1985, vol. 4, # 10, p. 1788 - 1792]

44
[ 4406-77-3 ]
[ 62930-28-3 ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium tri(isopropoxy)borohydride; dichloromethane; lithium diisopropyl amide In tetrahydrofuran byproducts: diisopropylamine, triisopropoxyborane; freshly prepared LDA is added dropwise to a mixt. of the boronic ester and CH2Cl2 at -78°C under N2, warming to room temp. over 12 h, borohydride is added at 0°C in 2 h; followed by (11)B NMR, solvent removal, residue is stirred with water, extn. with ether, ether extract is dried (MgSO4), evapn. and reesterification with 1,3-propanediol, distn.;

Reference： [1]Brown, Herbert C.; Singh, Shankar M. [Organometallics, 1986, vol. 5, # 5, p. 994 - 997]

45
[ 622-97-9 ]
[ 4406-77-3 ]
E-1-methyl-4-styryl-benzene [ No CAS ]
[ 3717-68-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium <i>tert</i>-butylate; oxygen; (-)-sparteine In isopropyl alcohol at 50℃; for 24h;

Reference： [1]Iwai, Yasumasa; Gligorich, Keith M.; Sigman, Matthew S. [Angewandte Chemie - International Edition, 2008, vol. 47, # 17, p. 3219 - 3222]

46
[ 4406-77-3 ]
[ 935529-75-2 ]
[ 935529-74-1 ]

Yield	Reaction Conditions	Operation in experiment
18%	With sodium methylate In methanol; dichloromethane room temp., 5 equiv. PhBO2(CH2)3, 15 mol% (CuOTf)2*C6H6, 10 equiv. NaOMe, in 4:1 CH2Cl2-MeOH;

Reference： [1]Xie, Jian-Hua; Nichols, Jason M.; Lubek, Conrad; Doyle, Michael P. [Chemical Communications, 2008, # 23, p. 2671 - 2673]

47
[ 4406-77-3 ]
[ 74-88-4 ]
[ 108-88-3 ]

Yield	Reaction Conditions	Operation in experiment
92 %Chromat.	With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 0.0833333h;	18 Examples 7-19; In Examples 7 - 19, as the aromatic boronic acid ester, boronic pinacol esters (400 µmol) to which various aromatic rings shown in Table 2 are bonded were used as a substrate. The other conditions were made to be the same as in the above-mentioned Example 1, that is to say, methyl iodide (10 µmol), tris(dibenzylideneacetone) dipalladium complex (0) (5 µmol), tri-o-tolylphosphine (20 µmol) and potassium carbonate (20 µmol) were used, and DMF was used as a solvent (in Example 12, DMF / water = 9/1 was also used). As a result, a methyl group was able to be bonded to various aromatic rings as shown in Table 2 in an extremely high yield. With respect to these aromatic rings, it was possible to carry out methylation in a high yield to a heterocycle such as a thiophenyl group shown in Example 14 or a furanyl group shown in Example 15 besides the benzene rings to which substituents shown in Examples 7 - 13 are bonded. Furthermore, it is remarkable that it is possible to carry out methylation in a high yield with respect to a heterocycle having strong basicity like a pyridinyl group of Example 16 or an isoquinolinyl group of Example 17. It is shown that the rapid methylation of the aromatic compound of the present invention is excellent in versatility.
92 %Chromat.	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium carbonate; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 60℃; for 0.0833333h; Inert atmosphere;

Reference： [1]Current Patent Assignee: INSTITUTE OF PHYSICAL AND CHEMICAL RESEARCH (RIKEN); HAMAMATSU PHOTONICS KK - EP2070897, 2009, A1 Location in patent: Page/Page column 9
[2]Location in patent: experimental part Doi, Hisashi; Ban, Ikuya; Nonoyama, Akihito; Sumi, Kengo; Kuang, Chunxiang; Hosoya, Takamitsu; Tsukada, Hideo; Suzuki, Masaaki [Chemistry - A European Journal, 2009, vol. 15, # 16, p. 4165 - 4171]

48
[ 4406-77-3 ]
[ 749860-75-1 ]
[ 1163687-52-2 ]
[ 1142935-75-8 ]
[ 4643-27-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 30% 2: 44%	With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); Selectfluor In acetonitrile at 80℃; for 0.25h;

Reference： [1]Location in patent: experimental part Zhang, Guozhu; Peng, Yu; Cui, Li; Zhang, Liming [Angewandte Chemie - International Edition, 2009, vol. 48, # 17, p. 3112 - 3115]

49
[ 4406-77-3 ]
[ 108-95-2 ]

Yield	Reaction Conditions	Operation in experiment
84%	With 1,10-Phenanthroline; copper(II) sulfate; potassium hydroxide In water at 20℃; for 10h;
82%	With dihydrogen peroxide In water at 20℃; for 0.25h; Green chemistry;

Reference： [1]Xu, Jimin; Wang, Xinyan; Shao, Changwei; Su, Deyong; Cheng, Guolin; Hu, Yuefei [Organic Letters, 2010, vol. 12, # 9, p. 1964 - 1967]
[2]Shin, Eun-Jae; Kim, Han-Sem; Joo, Seong-Ryu; Shin, Ueon Sang; Kim, Seung-Hoi [Catalysis Letters, 2019]

50
[ 4406-77-3 ]
[ 193819-24-8 ]
tetra-n-butylammonium phenyltrifluoroborate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With water In chloroform at 20℃; for 4h;
80%	In chloroform; water at 20℃; for 1h;

Reference： [1]Location in patent: experimental part Prakash, G. K. Surya; Pertusati, Fabrizio; Olah, George A. [Synthesis, 2011, # 2, p. 292 - 302]
[2]Pertusati, Fabrizio; Jog, Parag V.; Prakash, G.K. Surya [Organic Syntheses, 2013, vol. 90, p. 261 - 270]

51
[ 4406-77-3 ]
[ 1294517-65-9 ]
[ 1370412-45-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With dodecacarbonyl-triangulo-triruthenium In 3,3-dimethyl-butan-2-one at 140℃; for 36h; Inert atmosphere; regioselective reaction;
90%	With 3,3-dimethyl-butan-2-one; dodecacarbonyl-triangulo-triruthenium at 140℃; for 36h; Inert atmosphere;

Reference： [1]Dastbaravardeh, Navid; Schnuerch, Michael; Mihovilovic, Marko D. [Organic Letters, 2012, vol. 14, # 7, p. 1930 - 1933]
[2]Dastbaravardeh, Navid; Kirchner, Karl; Schnuerch, Michael; Mihovilovic, Marko D. [Journal of Organic Chemistry, 2013, vol. 78, # 2, p. 658 - 672]

52
[ 4406-77-3 ]
[ 1370412-53-5 ]
N-benzhydryl-3-methylpyridine-2-amine [ No CAS ]
[ 1384450-91-2 ]

Yield	Reaction Conditions	Operation in experiment
	With dodecacarbonyl-triangulo-triruthenium In 3,3-dimethyl-butan-2-one at 140℃; for 24h; Inert atmosphere; regioselective reaction;

Reference： [1]Dastbaravardeh, Navid; Schnuerch, Michael; Mihovilovic, Marko D. [Organic Letters, 2012, vol. 14, # 7, p. 1930 - 1933]

53
[ 4406-77-3 ]
[ 1248499-09-3 ]
[ 1370412-50-2 ]

Yield	Reaction Conditions	Operation in experiment
39%	With dodecacarbonyl-triangulo-triruthenium In 3,3-dimethyl-butan-2-one at 140℃; for 36h; Inert atmosphere; regioselective reaction;

Reference： [1]Dastbaravardeh, Navid; Schnuerch, Michael; Mihovilovic, Marko D. [Organic Letters, 2012, vol. 14, # 7, p. 1930 - 1933]

54
[ 4406-77-3 ]
[ 56826-32-5 ]
[ 1370412-49-9 ]

Yield	Reaction Conditions	Operation in experiment
75%	With dodecacarbonyl-triangulo-triruthenium In 3,3-dimethyl-butan-2-one at 140℃; for 36h; Inert atmosphere; regioselective reaction;
75%	With 3,3-dimethyl-butan-2-one; dodecacarbonyl-triangulo-triruthenium at 140℃; for 24h; Inert atmosphere;

55
[ 4406-77-3 ]
[ 70720-38-6 ]
N-benzhydryl-3-methylpyridine-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With dodecacarbonyl-triangulo-triruthenium In 3,3-dimethyl-butan-2-one at 140℃; for 24h; Inert atmosphere; regioselective reaction;
64%	With 3,3-dimethyl-butan-2-one; dodecacarbonyl-triangulo-triruthenium at 140℃; for 24h; Inert atmosphere;

56
[ 4406-77-3 ]
[ 70720-38-6 ]
[ 1370412-53-5 ]

Yield	Reaction Conditions	Operation in experiment
64%	With Al⁽²⁾H₄⁽¹⁺⁾*Li⁽¹⁺⁾ In tetrahydrofuran at 0℃; for 16h; Reflux;

Reference： [1]Dastbaravardeh, Navid; Schnuerch, Michael; Mihovilovic, Marko D. [Organic Letters, 2012, vol. 14, # 7, p. 1930 - 1933]

57
[ 116-14-3 ]
[ 4406-77-3 ]
[ 447-14-3 ]

Yield	Reaction Conditions	Operation in experiment
63 %Spectr.	With caesium carbonate; bis(dibenzylideneacetone)-palladium⁽⁰⁾; tricyclohexylphosphine In tetrahydrofuran; tetrahydrofuran-d8 at 100℃; for 5h;

Reference： [1]Ohashi, Masato; Saijo, Hiroki; Shibata, Mitsutoshi; Ogoshi, Sensuke [European Journal of Organic Chemistry, 2013, # 3, p. 443 - 447]

58
[ 4406-77-3 ]
2-(piperidin-1-yl)-3-trifluoromethylpyridine [ No CAS ]
[ 1431615-99-4 ]

Yield	Reaction Conditions	Operation in experiment
60%	With copper(ll) sulfate pentahydrate; dodecacarbonyl-triangulo-triruthenium; trimethyleneglycol In o-xylene at 140℃; for 24h; Inert atmosphere;

Reference： [1]Schwarz, Maria C.; Dastbaravardeh, Navid; Kirchner, Karl; Schnuerch, Michael; Mihovilovic, Marko D. [Monatshefte fur Chemie, 2013, vol. 144, # 4, p. 539 - 552]

59
[ 4406-77-3 ]
[ 1431616-14-6 ]
[ 1431616-08-8 ]

Yield	Reaction Conditions	Operation in experiment
28%	With copper(ll) sulfate pentahydrate; dodecacarbonyl-triangulo-triruthenium; trimethyleneglycol In o-xylene at 140℃; for 24h; Inert atmosphere;

Reference： [1]Schwarz, Maria C.; Dastbaravardeh, Navid; Kirchner, Karl; Schnuerch, Michael; Mihovilovic, Marko D. [Monatshefte fur Chemie, 2013, vol. 144, # 4, p. 539 - 552]

60
[ 4406-77-3 ]
[ 801306-50-3 ]
[ 1431616-09-9 ]

Yield	Reaction Conditions	Operation in experiment
25%	With copper(ll) sulfate pentahydrate; dodecacarbonyl-triangulo-triruthenium; trimethyleneglycol In o-xylene at 140℃; for 24h; Inert atmosphere;

Reference： [1]Schwarz, Maria C.; Dastbaravardeh, Navid; Kirchner, Karl; Schnuerch, Michael; Mihovilovic, Marko D. [Monatshefte fur Chemie, 2013, vol. 144, # 4, p. 539 - 552]

61
[ 4406-77-3 ]
[ 1355247-70-9 ]
[ 1431616-11-3 ]

Yield	Reaction Conditions	Operation in experiment
49%	With copper(ll) sulfate pentahydrate; dodecacarbonyl-triangulo-triruthenium; trimethyleneglycol In o-xylene at 140℃; for 24h; Inert atmosphere;

Reference： [1]Schwarz, Maria C.; Dastbaravardeh, Navid; Kirchner, Karl; Schnuerch, Michael; Mihovilovic, Marko D. [Monatshefte fur Chemie, 2013, vol. 144, # 4, p. 539 - 552]

62
[ 4406-77-3 ]
[ 1481723-17-4 ]
C₂₆H₅₂O₂Si₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: tris(triethylsilyl)silyl triflate With potassium hexamethylsilazane In toluene at -78℃; for 1h; Inert atmosphere; Stage #2: 2-Phenyl-1,3,2-dioxaborinane In toluene at -78 - 0℃; for 1h; Inert atmosphere;

Reference： [1]Oda, Susumu; Yamamoto, Hisashi [Angewandte Chemie - International Edition, 2013, vol. 52, # 31, p. 8165 - 8168][Angew. Chem., 2013, vol. 125, # 31, p. 8323 - 8326,4]

63
[ 4406-77-3 ]
[ 624-31-7 ]
[ 644-08-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium phosphate; <i>p</i>-toluidine; palladium dichloride In 1,4-dioxane at 115℃; for 24h; Inert atmosphere; chemoselective reaction;
91%	With potassium phosphate In 1,4-dioxane at 115℃; for 30h; Inert atmosphere;
93 %Chromat.	With copper(l) iodide; o-(di(tert-butyl)phosphino)-N,N-dimethylaniline; cesium fluoride In 1,4-dioxane; N,N-dimethyl-formamide at 120℃; for 48h; Glovebox; Inert atmosphere;

Reference： [1]Dhital, Raghu N.; Hashizume, Daisuke; Hu, Hao; Ishii, Rikako; Sato, Takuma; Sen, Abhijit; Takaya, Hikaru; Uozumi, Yasuhiro; Yamada, Yoichi M. A. [Organic Letters, 2020]
[2]Sen, Abhijit; Dhital, Raghu N.; Sato, Takuma; Ohno, Aya; Yamada, Yoichi M.A. [ACS Catalysis, 2020, vol. 10, # 24, p. 14410 - 14418]
[3]Gurung, Santosh K.; Thapa, Surendra; Kafle, Arjun; Dickie, Diane A.; Giri, Ramesh [Organic Letters, 2014, vol. 16, # 4, p. 1264 - 1267]

64
[ 153034-86-7 ]
[ 4406-77-3 ]
[ 42260-39-9 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 1264 - 1267

65
[ 104-92-7 ]
[ 4406-77-3 ]
[ 92-91-1 ]

Yield	Reaction Conditions	Operation in experiment
97%	With palladium on silica; potassium hydroxide In water for 0.116667h; Microwave irradiation; Green chemistry;

Reference： [1]Kotadia, Deepali A.; Patel, Urmila H.; Gandhi, Sahaj; Soni, Saurabh S. [RSC Advances, 2014, vol. 4, # 62, p. 32826 - 32833]

66
[ 4406-77-3 ]
[ 623-00-7 ]
[ 2920-38-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	With palladium on silica; potassium hydroxide In water for 0.116667h; Microwave irradiation; Green chemistry;

Reference： [1]Kotadia, Deepali A.; Patel, Urmila H.; Gandhi, Sahaj; Soni, Saurabh S. [RSC Advances, 2014, vol. 4, # 62, p. 32826 - 32833]

67
[ 4406-77-3 ]
C₂₆H₃₃NO₄S [ No CAS ]
(Z)-N-(2-benzylidene-4,4-bis(benzyloxymethyl)-cyclopentyl)-2-methylpropane-2-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74 mg	With [Rh(OH)(cod)]2 In methanol at 20℃; for 1h;	Without further purification, thecrude imine 14 was dissolved in MeOH (4.0 mL). [Rh(COD)OH]2(4.6 mg, 0.010 mmol) and phenylboronic acid 1,3-propanediol (61 mL, 0.40 mmol) were then added to the reaction mixture at room temperature. The mixture was stirred at room temperature for1 h and concentrated by rotary evaporation to remove the MeOH.The residue was dissolved in a minimal amount of CH2Cl2 and loaded onto a silica gel column for purification to yield product 15(74 mg,69% in two steps) as a white solid.

Reference： [1]Choi, Kyoungmin; Joo, Jung Min; Lee, Chulbom [Tetrahedron, 2015, vol. 71, # 35, p. 5910 - 5917]

68
[ 4406-77-3 ]
[ 103-71-9 ]
[ 93-98-1 ]