[ CAS No. 879291-27-7 ] {[proInfo.proName]}

Name: 879291-27-7|2-Phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine|97%
Brand: Ambeed
SKU: A129739
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2D 3D

Structure of 879291-27-7 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 879291-27-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 879291-27-7 ]

Product Details of [ 879291-27-7 ]

CAS No. :	879291-27-7	MDL No. :	MFCD12032565
Formula :	C₁₇H₂₀BNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XLBHFDXPYKKVFI-UHFFFAOYSA-N
M.W :	281.16	Pubchem ID :	45786526
Synonyms :

Calculated chemistry of [ 879291-27-7 ]

Physicochemical Properties

Num. heavy atoms :	21
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.35
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	86.15
TPSA :	31.35 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.53 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	3.5
Log Po/w (WLOGP) :	3.05
Log Po/w (MLOGP) :	1.89
Log Po/w (SILICOS-IT) :	2.9
Consensus Log Po/w :	2.27

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.08
Solubility :	0.0234 mg/ml ; 0.0000834 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.84
Solubility :	0.0405 mg/ml ; 0.000144 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-6.14
Solubility :	0.000205 mg/ml ; 0.000000728 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	3.16

Safety of [ 879291-27-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 879291-27-7 ]

* 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 [ 879291-27-7 ]

[ 879291-27-7 ] Synthesis Path-Downstream 1~34

1
[ 1008-89-5 ]
[ 73183-34-3 ]
[ 879291-27-7 ]
[ 879291-26-6 ]

Yield	Reaction Conditions	Operation in experiment
	With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer In hexane at 20℃; for 16h; Title compound not separated from byproducts;
	With [Ir(cod)2(μ-OMe)]2/dtbpy In hexane 16 h, room temp;; solvent removed;
	With (<SUP>iPr</SUP>PNP)CoCH<SUB>2</SUB>SiMe<SUB>3</SUB> In tetrahydrofuran at 80℃; for 43h; Inert atmosphere; Glovebox;

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In hexane at 20℃; for 16h; Glovebox; regioselective reaction;

Reference： [1]Mkhalid, Ibraheem A. I.; Coventry, David N.; Albesa-Jove, David; Batsanov, Andrei S.; Howard, Judith A. K.; Perutz, Robin N.; Marder, Todd B. [Angewandte Chemie - International Edition, 2006, vol. 45, # 3, p. 489 - 491]
[2]Mkhalid, Ibraheem A. I.; Coventry, David N.; Albesa-Jove, David; Batsanov, Andrei S.; Howard, Judith A. K.; Perutz, Robin N.; Marder, Todd B. [Angewandte Chemie - International Edition, 2006, vol. 45, # 3, p. 489 - 491]
[3]Obligacion, Jennifer V.; Semproni, Scott P.; Chirik, Paul J. [Journal of the American Chemical Society, 2014, vol. 136, # 11, p. 4133 - 4136]
[4]Sadler, Scott A.; Tajuddin, Hazmi; Mkhalid, Ibraheem A. I.; Batsanov, Andrei S.; Albesa-Jove, David; Cheung, Man Sing; Maxwell, Aoife C.; Shukla, Lena; Roberts, Bryan; Blakemore, David C.; Lin, Zhenyang; Marder, Todd B.; Steel, Patrick G. [Organic and Biomolecular Chemistry, 2014, vol. 12, # 37, p. 7318 - 7327]

2
[ 879291-27-7 ]
[ 1251729-45-9 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate In 1,4-dioxane; water at 80℃; for 18h; Inert atmosphere; Sealed tube;	D A pressure vial was charged with (S)-ethyl 2-((1s,4R)-4-(7-(bis((2- (trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[1 ,5-a]pyrimidin-5-yl)cyclohexyl)-2- fiuoroacetate (4.26 mmol, 3.01 g), 6-phenylpyridine-3-boronic acid pinacol ester (5.54 mmol, 1.56 g), potassium phosphate (12.78 mmol, 2.71 g), PdCI2(dppf)-CH2CI2 (0.43 mmol, 348 mg), and a solution of 9:1 1 ,4-dioxane:H20 (45 mL). The flask was flushed with argon and sealed. The reaction was stirred at 80° C for 18 hours. At 18 hours, the reaction was diluted with DCM (200 mL) and washed with H2O. The organic layer was collected and dried over Na2SO4. The resulting residue was purified via flash chromatography to yield the title compound (3.79 mmol, 2.78 g)

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2010/118207, 2010, A1 Location in patent: Page/Page column 346

3
[ 879291-27-7 ]
[ 1251729-64-2 ]
[ 1251729-65-3 ]

Yield	Reaction Conditions	Operation in experiment
74%	With potassium carbonate In 1,2-dimethoxyethane at 100℃; for 15h; Inert atmosphere; Sealed tube;	15.4 To a pressure tube were charged tert-buty 4-(7-(bis((2- (trimethylsilyl)emoxy)methyl)amin^carboxylate (4.2 g, 5.97 mmol), 2-phenyl-5-(4,4,5;5-tetramethyl-l,3)2-dioxaborolan-2- yl)pyridine (2 g, 7.1 mmol), PdCl2(dppf).CH2Cl2 (240 mg, 0.33 mmol), DME (16 mL) and 2 Na2C0 (8 mL). The mixture was briefly degassed with Argon and the tube was capped and heated at 1 0°C for 15 hours. On cooling, H20 (20 mL) and EtOAc (40 mL) and aqueous layer was extracted with EtOAc (3x) and combined organic layers were washed with brine once and dried (MgS04). After concentration in vacuo the residue was purified on silica gel. Elution with EtOAc/Hexanes (0-40%) gave tert-butyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(6-phenylpyridin-3 -yl)pyrazolo[ 1 ,5-a]pyrin idin-5- yl)piperidine-l-carboxylate (3.24 g, 74%).
57%	With potassium carbonate In 1,2-dimethoxyethane; water at 100℃; Inert atmosphere; Sealed tube;	9.H Step H - Preparation of tert-butyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3- (6-phenylpyridin-3-yl)pyrazolo[ 1 ,5-a]pyrimidin-5-yl)piperidine-l -carboxylate (Int-9h)To a pressure tube were charged tert-butyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[ l,5-a]pyrimidin-5-yl)piperidine- 1 -carboxylate (Int-9g, 1.7 g, 2.4 mmol), 2-phenyl-5-(4,4,5,5-tetramethyl- 1,3,2- dioxaborolan-2-yl)pyridine (800 mg, 2.8 mmol), [ l,l '-bis(diphenylphosphino)- ferrocene]dichloropalladium(II) complex with dichloromethane ( 1 : 1) ( 100 mg, 0.12 mmol), K2CO3 (666 mg, 4.8 mmol), DME ( 10 mL) and water (5 mL). The tube was degassed with Ar briefly, capped and heated at 100 0C with stirring overnight. After cooling, the reaction mixture was diluted with EtOAc and water, the organic layer was isolated, washed with brine and dried (MgSU4). After the solvent was removed under reduced pressure, the residue was purified on silica. Elution with EtOAc in hexanes (0- 50%) gave tert-buty 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(6- OC2009.701891 phenylpyridin-3-yl)pyrazolo[ 1 ,5-a]pyrimidin-5-yl)piperidine- 1 -carboxy late (Int-9h) ( 1 g, 57%). LC/MS: m/z = 731 (M+H+).

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2012/27234, 2012, A1 Location in patent: Page/Page column 53; 54
[2]Current Patent Assignee: MERCK & CO INC - WO2011/2887, 2011, A1 Location in patent: Page/Page column 90-91

4
[ 879291-27-7 ]
[ 1251729-80-2 ]
[ 1251730-16-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate In 1,4-dioxane; water at 70℃; Inert atmosphere;	11.A Step A - Synthesis of 5-chloro-3-(6-phenylpyridin-3-yl)-N,N-bis((2- (trimethylsityl)ethoxy)methyl)pyrazolo[l,5-a]pyrimidin-7-amine (Int-lla)2-phenyl-5-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)pyridine (2.38 mmol, 675 mg), K3PO4 (5.96 mmol, 1264 mg), and PdCl2(dppf)-CH2Cl2 (0.20 mmol, 162 mg) was added to a solution of 5-chloro-3-iodo-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[ l ,5-a]pyrimidin-7-amine (Int-lOa, 1.98 mmol, 1 101 mg) (prepared as described in Step a of Example 10) in dioxane (18 mL) and H2O (3 mL). The resulting solution was stirred at 70 ° C under argon overnight. The mixture was diluted with H2O and then extracted with ethyl acetate (x2). The combined organic layers were washed with brine and dried with Na2SO4. Evaporation and purification by column chromatography afforded 5-chloro-3-(6-phenylpyridin-3- yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[l,5-a]pyrimidin-7-amine (Int- OC2009.701898Ha): LCMS tR = 3.36 Min (5 min run, UV 254,)- Mass calculated for, M+ 581.2, observed LC/MS m/z 582.2 (M+H).
	With potassium phosphate In 1,4-dioxane; water at 70℃; Inert atmosphere;	9.1 2-phenyl-5-(4J4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine (675 mg, 2.38 mmol), K3P04 (1264 mg, 5.96 mmol), and PdCl2(dppf)-CH2Cl2 (162 mg, 0.20 mmol) was added to a solution of 5-chloro-3-iodo-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[l,5- a]pyrimidin-7-amine (1101 mg, 1.98 mmol) in dioxane (18 mL) and ¾0 (3 mL). The resulting solution was stirred at 70° C under argon overnight. The mixture was diluted with H20 and then extracted with ethyl acetate (x2). The combined organic layers were washed with brine and dried with Na2SC>4. Evaporation and purification by column chromatography afforded 5-chloro-3-(6-phenylpyridin-3-yl)-NJN-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[l,5- a]pyrimidin-7-amine: LCMS tR = 3.36 Min (5 min run, UV254nm). Mass calculated for, M+ 581.2, observed LC/MS m z 582.2 (M+H).

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2011/2887, 2011, A1 Location in patent: Page/Page column 97-98
[2]Current Patent Assignee: MERCK & CO INC - WO2012/27240, 2012, A1 Location in patent: Page/Page column 59; 60

5
[ 879291-27-7 ]
[ 1251730-28-5 ]
[ 1251730-26-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate In 1,4-dioxane; water at 100℃; for 18h; Inert atmosphere;	12.D Step D - Synthesis of tert-butyl 4-((7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(6- phenylpyridin-3-yl)pyrazolo[ 1 ,5-a]pyrimidin-5-yl)methyl)piperidine-l -carboxylate (Int-I2f)OC2009.70181032-phenyl-5-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)pyridine ( 1.32 mmol, 370 mg), K3PO4 (3.04 mmol, 644 mg), and PdCl2(dppf)• CH2Cl2 (0.10 mmol, 83 mg) was added to a solution of tert-butyl 4-((7-(bis((2- (trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[ l,5-a]pyrimidin-5- yl)methyl)piperidine-l-carboxylate (Int-12e, 1.02 mmol, 726 mg) in dioxane (6 mL) and H2O (ImL). The resulting solution was stirred at 1000C under argon for 18 hours. The mixture was diluted with H2O and then extracted with ethyl acetate (x2). The combined organic layers were washed with brine and dried with Na2SO4. Evaporation and purification by column chromatography afforded tert-butyl 4-((7-(bis((2- (trimethylsilyl)ethoxy)methyl)amino)-3-(6-phenylpyridin-3-yl)pyrazolo[l,5- a]pyrimidin-5-yl)rnethyl)piperidine-l-carboxylate (Int-12f): LCMS tR = 3.47 Min (5 min run, UV 254nm). Mass calculated for, M+ 744.2, observed m/z 745.2 (M+H).

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2011/2887, 2011, A1 Location in patent: Page/Page column 102-103

6
[ 879291-27-7 ]
[ 1251730-08-1 ]
[ 1251730-09-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate In 1,4-dioxane; water at 90℃; Inert atmosphere;	3.A Step A - Synthesis of Intermediate Int-3a OC2009.7018452-phenyl-5-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)pyridine (616 mmol, 2.19 mg), K3PO4 (5.06 mmol, 1073 mg), and PdCl2(dppf) CH2Cl2 (0.17 mmol, 138 mg) was added to a solution of Int-lg (1.69 mmol, 1 100 mg) in dioxane (15 mL) and H2O (3 mL). The resulting solution was stirred at 900C under argon overnight. The mixture was diluted with H2O and then extracted with ethyl acetate (x2). The combined organic layers were washed with brine and dried with Na2SO4. Evaporation and purification by column chromatography afforded Int-3a: LCMS tR = 2.69 min (5 min run, UV 254nm)- Mass calculated for, M+ 679.3, observed m/z 680.3 (M+H).
	With potassium phosphate In 1,4-dioxane; water at 90℃; Inert atmosphere;	1.4 2-phenyl-5-(4;4,5>5 etramethyl-l,352-dioxaborolan-2-yl)pyridine (616 mg, 2.19 mmoL), K3PO4 (1073 mg, 5.06 mmol), and PdCI2(dppf) · CH2C12 (138 mg, 0.17 mmol) was added to a solution of 3-iodo-5-(tetrahydro-l,l-dioxido-2H-thiopyran-4-yl)-N,N-bis((2- (trimethylsilyl)ethoxy)methyl)pyrazolo[lf5~a]pyrimidin-7-amine (1 100 mg, 1.69 mmol) in dioxane (15 mL) and H20 (3 mL). The resulting solution was stirred at 90° C under argon overnight. The mixture was diluted with ¾0 and then extracted with ethyl acetate (x2). The combined organic layers were washed with brine and dried with Na2S04. Evaporation and purification by column chromatography afforded 3-(6-phenylpyridin-3-yl)-5-(tetrahydro-l,l- dioxido-2H-thiopyran-4-yl)-N?N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo [1,5- a]pyrimidin-7-amine: LCMS t = 2.69 Min (5 min run, UV254nm)- Mass calculated for, M+ 679.3, observed rn/z 680.3 (M+H).

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2011/2887, 2011, A1 Location in patent: Page/Page column 44-45
[2]Current Patent Assignee: MERCK & CO INC - WO2012/27240, 2012, A1 Location in patent: Page/Page column 37; 38

7
[ 879291-27-7 ]
[ 1094568-09-8 ]
[ 1094567-95-9 ]

Yield	Reaction Conditions	Operation in experiment
38%	With sodium carbonate In 1,2-dimethoxyethane; water at 100℃; for 16h; Sealed tube; Inert atmosphere;	63.D Step D - Preparation of Compound 60 A 10 mL sealed tube was charged with compound 63C (110 mg, 0.251 mmol), compound 62A (85 mg, 0.301 mmol, from Example 62), Na2C03 (53 mg, 0.502 mmol), Pd(PPh3)4 (29 mg, 0.025 mmol) and argon-degassed dimethoxyethane/water (2:1, 5 mL). The tube was placed in an oil bath at 100 °C and allowed to remain at this temperature for 16 hours, then the tube was removed from the heat bath and allowed to cool to room temperature. The cooled reaction mixture was diluted with brine (50 mL) and CH2CI2 (50 mL), then separated and the aqueous phase was extracted with CH2CI2 (2 x 50 mL). The combined organic extracts were dried over Na2S0 , filtered and concentrated in vacuo. The residue obtained was purified using flash column chromatography (silica gel, 20:80, CH2Cl2 EtOAc) to provide a crude oil which was further purified using semi-preparative HPLC (Luna C 18, CH3CN/water with 0.05% TFA) to provide a solid product. This solid product was dissolved in a mixture of CH3CN and water and the resulting solution was freeze-dried for about 15 hours to provide compound 60 (49 mg, 38%) as an off-white solid: m.p. 124-128 °C; 1H N R (300 MHz, CDCI3) δ 8.70 (s, 1H), 8.03-7.98 (m, 3H), 7.80 (d, J- 8.4 Hz, IH), 7.50-7.44 (m, 3H), 7.28 (m, 1H), 6.98-6.93 (m, 1H), 6.84-6.81 (m, 1H), 5.36-fs, 2H¾ 4.09 (q, J= 6.9 Hz, 2H), 3.55 (s, 2H), 1.30 (t, J - 6.9 Hz, 3H), 1.25 (s, 6H); ESI MS m/z 513 [M + H]+.
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In water; acetonitrile at 130℃; for 0.5h;

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2011/79000, 2011, A1 Location in patent: Page/Page column 64; 65
[2]Location in patent: scheme or table Brumfield, Stephanie; Matasi, Julius J.; Tulshian, Deen; Czarniecki, Michael; Greenlee, William; Garlisi, Charles; Qiu, Hongchen; Devito, Kristine; Chen, Shu-Cheng; Sun, Yongliang; Bertorelli, Rosalia; Ansell, Justin; Geiss, William; Le, Van-Duc; Martin, Gregory S.; Vellekoop, Samuel A.; Haber, James; Allard, Melissa L. [Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 24, p. 7287 - 7290]

8
[ 16110-09-1 ]
[ 879291-27-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / ethanol; water; toluene / 24 h / 80 °C 2: potassium acetate; XPhos / 1,4-dioxane / 24 h / 80 °C
	Multi-step reaction with 2 steps 1: sodium carbonate / PdCl₂(PPh₂(CH₂)4PPh₂) / toluene; ethanol; water / 3 h / Reflux 2: tricyclohexylphosphine; potassium acetate / bis(dibenzylideneacetone)-palladium⁽⁰⁾ / 1,4-dioxane / 16 h / 80 °C / Sealed tube; Inert atmosphere

9
[ 58254-76-5 ]
[ 73183-34-3 ]
2-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With potassium acetate; tricyclohexylphosphine In 1,4-dioxane at 80℃; for 16h; Sealed tube; Inert atmosphere;	62.B Step B - Preparation of Compound 62ΛA 150 mL sealed tube was charged with bis(dibenzylideneacetone)palladium (87 mg, 0.152 mmol), tricyclohexylphosphine (102 mg, 0.364 mmol) and nitrogen-degassed 1 ,4- dioxane (32 mL). After stirring at room temperature for 30 min under nitrogen,bis(pinacolato)diboron (1.41 g, 5.56 mmol), OAc (0.744 g, 7.59 mmol) and 5-chloro-2- phenylpyridine (0.959 g, 5.06 mmol, from Step A) was added to the reaction mixture. The tube was sealed and place in an oil bath at 80 °C for 16 hours. The mixture was cooled to room temperature, diluted with brine (50 mL) and CH2CI2 (100 mL) and the layers were separated. The aqueous phase was extracted with CJ¾C12 (10-0 mL) and the combined organics washed with brine (150 mL), dried over Na2S04, filtered and concentrated. Purification by flash column chromatography (silica gel, 50:50 CH2CI2/EtOAc) provided compound 62A(0.569 g, 40%) as a white solid.
	With potassium acetate; XPhos In 1,4-dioxane at 80℃; for 24h;
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 12h;	1-5 Add 100mmol of M1, 110mmol of pinacol diborate,29.4g potassium acetate (300mmol), 800ml dioxane,And add 1 mol% of dichloro[1,1'-bis(diphenylphosphine)ferrocene]palladium (Pd(dppf)Cl2).React at 100°C for 12h. After the completion of the reaction, the reaction was stopped, and the reactant was cooled to room temperature, water was added, the organic phase was separated, concentrated to obtain a white solid, filtered, and washed with water.The obtained solid was recrystallized and purified with toluene to obtain a white powder M2.Among them, the added amount of Pd(dppf)Cl2 is 1 mol% of M1.

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2011/79000, 2011, A1 Location in patent: Page/Page column 63
[2]Location in patent: scheme or table Brumfield, Stephanie; Matasi, Julius J.; Tulshian, Deen; Czarniecki, Michael; Greenlee, William; Garlisi, Charles; Qiu, Hongchen; Devito, Kristine; Chen, Shu-Cheng; Sun, Yongliang; Bertorelli, Rosalia; Ansell, Justin; Geiss, William; Le, Van-Duc; Martin, Gregory S.; Vellekoop, Samuel A.; Haber, James; Allard, Melissa L. [Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 24, p. 7287 - 7290]
[3]Current Patent Assignee: YANTAI XIANHUA CHEM-TECH CO LTD - CN113264871, 2021, A Location in patent: Paragraph 0108-0109; 0111; 0120; 0129; 0137; 0148

10
[ 98-80-6 ]
[ 879291-27-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / ethanol; water; toluene / 24 h / 80 °C 2: potassium acetate; XPhos / 1,4-dioxane / 24 h / 80 °C
	Multi-step reaction with 2 steps 1: sodium carbonate / PdCl₂(PPh₂(CH₂)4PPh₂) / toluene; ethanol; water / 3 h / Reflux 2: tricyclohexylphosphine; potassium acetate / bis(dibenzylideneacetone)-palladium⁽⁰⁾ / 1,4-dioxane / 16 h / 80 °C / Sealed tube; Inert atmosphere
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / water; 1,2-dimethoxyethane / Inert atmosphere; Reflux 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / 1,4-dioxane / 3 h / 90 °C / Inert atmosphere

	Multi-step reaction with 2 steps 1.1: potassium carbonate / 1,2-dimethoxyethane; water / 0.5 h / Inert atmosphere 1.2: Reflux 2.1: potassium acetate / 1,4-dioxane / 0.5 h / Inert atmosphere 2.2: 3 h / 90 °C
	Multi-step reaction with 2 steps 1: potassium carbonate; palladium diacetate; triphenylphosphine / tetrahydrofuran; water / 48 h / 90 °C 2: C₃₄H₅₁AlN₃P₂Rh; tert-butylethylene / 1,4-dioxane / 15 h / 150 °C / Glovebox
	Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran; water / 12 h / 120 °C 2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 12 h / 100 °C

Reference： [1]Brumfield, Stephanie; Matasi, Julius J.; Tulshian, Deen; Czarniecki, Michael; Greenlee, William; Garlisi, Charles; Qiu, Hongchen; Devito, Kristine; Chen, Shu-Cheng; Sun, Yongliang; Bertorelli, Rosalia; Ansell, Justin; Geiss, William; Le, Van-Duc; Martin, Gregory S.; Vellekoop, Samuel A.; Haber, James; Allard, Melissa L. [Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 24, p. 7287 - 7290]
[2]Current Patent Assignee: MERCK & CO INC - WO2011/79000, 2011, A1
[3]Current Patent Assignee: UNIVERSAL DISPLAY CORP - US2015/307535, 2015, A1
[4]Current Patent Assignee: UNIVERSAL DISPLAY CORP - US9966541, 2018, B2
[5]Hara, Naofumi; Nakao, Yoshiaki; Saito, Teruhiko; Seki, Rin [Journal of the American Chemical Society, 2021, vol. 143, # 17, p. 6388 - 6394]
[6]Current Patent Assignee: YANTAI XIANHUA CHEM-TECH CO LTD - CN113264871, 2021, A

11
[ 879291-27-7 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 15 h / 100 °C 2: N-Bromosuccinimide / dichloromethane; acetonitrile / 0.5 h / 20 °C 3: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾; bis(tri-t-butylphosphine)palladium⁽⁰⁾ / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 4: 2,6-dimethylpyridine; sodium periodate / osmium(VIII) oxide / 1,4-dioxane; water; <i>tert</i>-butyl alcohol 5: sodium hydroxide; sodium tetrahydroborate; methanol / 0.5 h 6: water / 0.33 h 7: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.17 h / 20 °C