[ CAS No. 75927-49-0 ]

Name: 75927-49-0|Pinacol vinylboronate|97% (stablized with PTZ)
Brand: Ambeed
SKU: A469455
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Quality Control of [ 75927-49-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 75927-49-0 ]

SDS Specification

Alternatived Products of [ 75927-49-0 ]

Product Details of [ 75927-49-0 ]

CAS No. :	75927-49-0	MDL No. :	MFCD00192492
Formula :	C₈H₁₅BO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DPGSPRJLAZGUBQ-UHFFFAOYSA-N
M.W :	154.01	Pubchem ID :	5233012
Synonyms :

Calculated chemistry of [ 75927-49-0 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.75
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	47.04
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) :	-5.78 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.06
Log Po/w (WLOGP) :	1.8
Log Po/w (MLOGP) :	0.76
Log Po/w (SILICOS-IT) :	0.92
Consensus Log Po/w :	1.11

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.03
Solubility :	1.45 mg/ml ; 0.0094 mol/l
Class :	Soluble
Log S (Ali) :	-2.08
Solubility :	1.29 mg/ml ; 0.00838 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.91
Solubility :	1.9 mg/ml ; 0.0123 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.05

Safety of [ 75927-49-0 ]

Signal Word:	Danger	Class:	3
Precautionary Statements:	P210-P240-P241-P242-P243-P261-P264-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P312-P363-P370+P378-P403+P233-P501	UN#:	3272
Hazard Statements:	H225-H315-H319-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 75927-49-0 ]

* 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 [ 75927-49-0 ]
Downstream synthetic route of [ 75927-49-0 ]

[ 75927-49-0 ] Synthesis Path-Upstream 1~7

1
[ 76-09-5 ]
[ 151293-63-9 ]
[ 75927-49-0 ]

Yield	Reaction Conditions	Operation in experiment
252 g	at 85 - 90℃; Inert atmosphere	Under a nitrogen atmosphere, 193 g of pinacol and 14 g of 2,6-di-t-butyl-4-methylphenol were charged in a 1 L reaction flask,To 85-90 ° C, until the pinacol is completely melted, the slow trickle-down of the intermediate reaction, attention to control the dropping rate, then atmospheric steamDistillation device, the reaction of diisopropylamine separation, after the end of the reaction temperature to obtain colorless transparent liquid vinyl boronic acid which252 g of the alcohol ester, and GC: 99.1percent (excluding the polymerization inhibitor).

Reference： [1] Patent: CN105503926, 2016, A, . Location in patent: Paragraph 0018

2
[ 74-85-1 ]
[ 25015-63-8 ]
[ 82954-89-0 ]
[ 75927-49-0 ]

Reference： [1] Journal of the American Chemical Society, 2002, vol. 124, # 20, p. 5624 - 5625
[2] Journal of the American Chemical Society, 2002, vol. 124, # 20, p. 5624 - 5625

3
[ 76-09-5 ]
[ 4363-34-2 ]
[ 75927-49-0 ]

Reference： [1] Journal of Organic Chemistry, 2003, vol. 68, # 15, p. 6031 - 6034

4
[ 623-73-4 ]
[ 75927-49-0 ]
[ 1215107-29-1 ]

Reference： [1] Patent: WO2010/30538, 2010, A2, . Location in patent: Page/Page column 212-213
[2] Patent: WO2011/112186, 2011, A1, . Location in patent: Page/Page column 211-212
[3] Patent: WO2015/52226, 2015, A1, . Location in patent: Paragraph 0187

5
[ 402-43-7 ]
[ 75927-49-0 ]
[ 1242770-50-8 ]

Reference： [1] New Journal of Chemistry, 2017, vol. 41, # 8, p. 3172 - 3176

6
[ 1813-97-4 ]
[ 75927-49-0 ]
[ 1242770-50-8 ]

Reference： [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 16, p. 3328 - 3333

7
[ 392-83-6 ]
[ 75927-49-0 ]
[ 1294009-25-8 ]

Reference： [1] New Journal of Chemistry, 2017, vol. 41, # 8, p. 3172 - 3176

[ 75927-49-0 ] Synthesis Path-Downstream 1~68

1
[ 37067-95-1 ]
[ 75927-49-0 ]
[ 16975-71-6 ]

Reference： [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 2214 - 2222

2
[ 623-73-4 ]
[ 75927-49-0 ]
[ 1215107-29-1 ]

Yield	Reaction Conditions	Operation in experiment
	palladium diacetate; In diethyl ether;	Step 1: Preparation of compound 12, To a solution of 4,4,5, 5-tetramethyl-2-vinyl- 1,3,2-dioxaborolane (0.31 g} 2.0 mmol) and PdOAc2 (4.5 mg, 0.02 mmol) in anhydrous Ether (3 mL) was added a solution of ethyl 2-diazoacetate (0,57 g, 5.0 mmol) in ether (2 mL) dropwise under N2. During the halfway of the addition, additional PdOAc2 (4.49 mg, 0.02 mmoi) was added. When N2 evolution had ceased, the reaction mixture was filtered through activated neutral aluminum oxide and washed with ether. The filtrate was concentrated to yield compound 12 (0.50 g, 2.0 mmol) as a yellow oil. The crude product was used without further purification.
	palladium diacetate; In diethyl ether;Inert atmosphere;	To a solution of 4,4,5,5-tetramethyl-2-vinyl- 1,3,2-dioxaborolane (0.31 g, 2.0 mmol) and PdOAc2 (4.5 mg, 0.02 mmol) in anhydrous Ether (3 mL) was added a solution of ethyl 2-diazoacetate (0.57 g, 5.0 mmol) in ether (2 mL) dropwise under N2. During the halfway of the addition, additional PdOAc2 (4.49 mg, 0.02 mmol) was added. When 2 evolution had ceased, the reaction mixture was filtered through activated neutral aluminum oxide and washed with ether. The filtrate was concentrated to yield compound 12 (0.50 g, 2.0 mmol) as a yellow oil. The crude product was used without further purification.
	With palladium diacetate; In diethyl ether; at 20.0℃; for 1.33333h;	To a solution of 2-ethenyl-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (10.0 g, 4.38 mmol) and palladium acetate (166 mg, 0.44 mmol) in ether (50 mL) was added ethyl 2-diazoacetate (6.60 g, 5.47mmol) in ether (20 mL) dropwise for 10 min at room temperature. Palladium acetate (166 mg, 0.44 mmol) and ethyl 2-diazoacetate (6.60 g, 5.47 mmol) in ether (20 mL) were again added dropwise for another 10 min. The resulting solution was then stirred for 1 h at room temperature. After filtration through active aluminum oxide, the filtrate was concentrated in vacuo to afford ethyl 2-(tetramethyl- l,3,2-dioxaborolan-2-yl)cyclopropane-l-carboxylate as yellow oil (24.0 g). The crude product was used in the next step without further purification. .

Reference： [1]Patent: WO2010/30538,2010,A2 .Location in patent: Page/Page column 212-213
[2]Patent: WO2011/112186,2011,A1 .Location in patent: Page/Page column 211-212
[3]Patent: WO2015/52226,2015,A1 .Location in patent: Paragraph 0187

3
[ 736991-39-2 ]
[ 75927-49-0 ]
[ 1247002-63-6 ]

Yield	Reaction Conditions	Operation in experiment
77%	With triethylamine;bis(tri-t-butylphosphine)palladium(0); In toluene; at 80℃; for 2h;Inert atmosphere; Autoclave; Microwave irradiation;	Exampel A51. Synthesis of (lR.2S)-(E)-5'-methoxy-2-(3-(4-(2-morpholinoethvnstyryl)- l Eta-indazol-6-yl)spiro[cyclopropane-K3'-indolinl-2'-one 2.2.2-trifluoroacetateA . (E)-4- (4- (2-(4, 4, 5, 5-tetramethyl-l, 3, 2-dioxaborolan-2-yl)vinyl) phenethyl)morpholineTo a mixture of <strong>[736991-39-2]4-(4-bromophenethyl)morpholine</strong> (731 mg, 2.71 mmol) and4,4,5, 5-tetramethyl-2-vinyl-l ,3,2-dioxaborolane (0.5 mL, 2.95 mmol, 1.1 eq.) and toluene (10 mL) in a 20 mL microwave vial was added Et3N (0.76 mL, 5.4 mmol, 2 eq.), followed by Pd(P'Bu3)2 (14 mg, 0.027 mmol, 1 mol%). The resulting mixture was purged with argon, then capped and heated at 80 0C (oil temp.) for 2 h. After cooling to rt, it was quenched with sat. NaHCO3 (10 mL), H2O (10 niL), extracted with EtOAc (30 mL x 2) and dried (Na2SO4). After evaporation of the solvents, the residue was purified by Biotage column system (EtOAc/hex gradient: 0-100%) to give (E)-4-(4-(2-(4,4,5,5- tetramethyl-l ,3,2-dioxaborolan-2-yl)vinyl)phenethyl)mophiholine as a white solid (714 5 mg, 77%). 1 H NMR (400 MHz, CDCl3) delta 7.42 (d, J = 8.0 Hz, 2H), 7.38 (d, J = 19.0 Hz, I H), 7.19 (d, J = 7.8 Hz, 2H), 6.13 (d, J = 18.3 Hz, I H), 3.75 (t, J = 4.4 Hz, 4H), 2.84- 2.77 (m, 2H), 2.63-2.56 (m, 2H), 2.53 (br, pseudo s, 4H), 1.32 (s, 12H).
77%	With triethylamine;bis(tri-t-butylphosphine)palladium(0); In toluene; at 80℃; for 2h;Inert atmosphere; Microwave irradiation;	A. (E)-4-(4-(2-(4, 4, 5, 5-tetramethyl-l, 3,2-dioxaborolan-2-yl)vinyl) phenethyl)morpholine[00197] To a mixture of <strong>[736991-39-2]4-(4-bromophenethyl)morpholine</strong> (731 mg, 2.71 mmol) and 4,4,5,5-tetramethyl-2-vinyl-l,3,2-dioxaborolane (0.5 mL, 2.95 mmol, 1.1 eq.) and toluene (10 mL) in a 20 mL microwave vial was added Et3N (0.76 mL, 5.4 mmol, 2 eq.), followed by Pd(P'Bu3)2 (14 mg, 0.027 mmol, 1 mol%). The resulting mixture was purged with argon, then capped and heated at 80 C (oil temp.) for 2 h. After cooling to rt, it was quenched with sat. NaHC03 (10 mL), H20 (10 mL), extracted with EtOAc (30 mL x 2) and dried(Na2SC>4). After evaporation of the solvents, the residue was purified by Biotage column system (EtOAc hex gradient: 0-100%) to give (E)-4-(4-(2-(4,4,5,5-tetramethyl- 1,3,2- dioxaborolan-2-yl)vinyl)phenethyl)mo holine as a white solid (714 mg, 77%). NMR (400 MHz, CDC13) delta 7.42 (d, J = 8.0 Hz, 2H), 7.38 (d, J = 19.0 Hz, 1H), 7.19 (d, J = 7.8 Hz, 2H), 6.13 (d, J = 18.3 Hz, 1 H), 3.75 (t, J = 4.4 Hz, 4H), 2.84-2.77 (m, 2H), 2.63-2.56 (m, 2H), 2.53 (br, pseudo s, 4H), 1.32 (s, 12H).

Reference： [1]Patent: WO2010/115279,2010,A1 .Location in patent: Page/Page column 171-172
[2]Patent: WO2011/123946,2011,A1 .Location in patent: Page/Page column 81

4
[ 132833-51-3 ]
[ 75927-49-0 ]
[ 933986-62-0 ]

Yield	Reaction Conditions	Operation in experiment
71%	With triethylamine;bis(tri-t-butylphosphine)palladium(0); In toluene; at 80℃; for 2h;Inert atmosphere; Microwave irradiation;	Synthesis of (E)-4-("4-(2-(4.4.5,5-tetramethyl-L3,2-dioxaborolan-2-yl)vinyl)benzyl) morpholine[00124] The title compound (4.35 g, 71 %) was obtained as a white to yellow solid from <strong>[132833-51-3]4-(4-bromobenzyl)morpholine</strong> (4.18 g, 16.3 mmol) and 4,4,5,5-tetramethyl-2-vinyl- 1 ,3,2- dioxaborolane (3 mL, 17.7 mmol, 1.1 eq.) using the method for the preparation of Example A51A (PhCH3 = 30 mL, 1 mol% Pd(P,Bu3)2, 80 C, 1 h). NMR (400 MHz, CDC13) delta 7.45 (d, J = 8.0 Hz, 2H), 7.40 (d, J = 18.4 Hz, 1H), 7.31 (d, J = 8.0 Hz, 2H), 6.16 (d, J = 18.0 Hz, 1H), 3.72 (t, J = 4.4 Hz, 4H), 3.50 (s, 2H), 2.47-2.42 (m, 4H), 1.32 (s, 12H); MS ESI 330.1 [M + H]+, calcd for [C19H28BN03 + H]+ 330.2.; Example A51. Synthesis of 1Kappa.25 -(Epsilon)-5'^6^omicronchinu-2-(3-(4-(2^omicron ^1etaomicron6Phinu1 5GammanuGammanu1 -1Eta- indazol-6-yl)spiro[cyclopropane- 1 ,3'-indolinl-2'-one 2,2,2-trifluoroacetateA. (E)-4-(4-(2-(4, 4, 5, 5-tetramethyl-l, 3,2-dioxaborolan-2-yl)vinyl) phenethyl)morpholine[00197] To a mixture of 4-(4-bromophenethyl)morpholine (731 mg, 2.71 mmol) and 4,4,5,5-tetramethyl-2-vinyl-l,3,2-dioxaborolane (0.5 mL, 2.95 mmol, 1.1 eq.) and toluene (10 mL) in a 20 mL microwave vial was added Et3N (0.76 mL, 5.4 mmol, 2 eq.), followed by Pd(P'Bu3)2 (14 mg, 0.027 mmol, 1 mol%). The resulting mixture was purged with argon, then capped and heated at 80 C (oil temp.) for 2 h. After cooling to rt, it was quenched with sat. NaHC03 (10 mL), H20 (10 mL), extracted with EtOAc (30 mL x 2) and dried(Na2SC>4). After evaporation of the solvents, the residue was purified by Biotage column system (EtOAc hex gradient: 0-100%) to give (E)-4-(4-(2-(4,4,5,5-tetramethyl- 1,3,2- dioxaborolan-2-yl)vinyl)phenethyl)mo holine as a white solid (714 mg, 77%). NMR (400 MHz, CDC13) delta 7.42 (d, J = 8.0 Hz, 2H), 7.38 (d, J = 19.0 Hz, 1H), 7.19 (d, J = 7.8 Hz, 2H), 6.13 (d, J = 18.3 Hz, 1 H), 3.75 (t, J = 4.4 Hz, 4H), 2.84-2.77 (m, 2H), 2.63-2.56 (m, 2H), 2.53 (br, pseudo s, 4H), 1.32 (s, 12H).
	With bis(tri-t-butylphosphine)palladium(0); N-ethyl-N,N-diisopropylamine; In toluene; for 3h;Inert atmosphere; Heating;	General procedure: Bromoaryl derivatives (5mmol, 1.0 equiv), pinacol vinylboronate (6mmol, 1.2 equiv) and DIEA (20mmol, 2.0 equiv) were dissolved in toluene (10mL), then air was immediately replaced 5 times with nitrogen after the addition of bis(tri-tert-butylphosphine)palladium(0). The reaction mixture stirred at 95 for 3 h. Upon completion of the reaction as determined by TLC, the solvent was removed under reduced pressure. the residue was dissolved in dichloromethane and filtered by diatomite. The filtrate was washed twice with water and concentrated under reduced pressure. The crude compound was purified by column chromatography eluting with ethyl acetate: hexane to afford the desired compound 8 as a liquid. Yield: 60%.

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 130 - 146
[2]New Journal of Chemistry,2017,vol. 41,p. 3172 - 3176
[3]Patent: WO2011/123946,2011,A1 .Location in patent: Page/Page column 41
[4]Journal of Medicinal Chemistry,2015,vol. 58,p. 147 - 169
[5]Bioorganic and medicinal chemistry letters,2020

5
[ 41604-19-7 ]
[ 75927-49-0 ]
[ 63444-55-3 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 9391 - 9396
[2]European Journal of Organic Chemistry,2017,vol. 2017,p. 4859 - 4863
[3]ChemCatChem,2019,vol. 11,p. 5814 - 5820

6
[ 10386-27-3 ]
[ 75927-49-0 ]
[ 98436-74-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;palladium diacetate; triphenylphosphine; In 1,4-dioxane; at 85℃; for 4h;Inert atmosphere;	Example A3. General experimental for the Suzuki coupling of aryl bromides or chlorides with boronic acidsGeneral Scheme:K2C03, Pd(OAc)2 Ph3P, dioxaneRepresentative SchePh3P, dioxaneA solution of the aryl bromide or aryl chloride (e.g., 6-bromonicotinonitrile, 1 equiv), 4,4,5,5-tetramethyl -2-vinyl-l,3,2- dioxaborolane (2 equiv), K2C03 (2 equiv), Pd(AcO)2 (0.4 equiv) and PI13P (0.8 equiv) in 1,4-dioxane was stirred under N2 at 85 °C until the reaction was complete (approximately 4 h). After cooling to room temperature, the mixture was quenched with water (50 mL) and extracted with ethyl acetate (3 x 50 mL). The combined organic layers were dried over Na2S04 and concentrated under reduced pressure. The crude vinyl-containing product (e.g., 2-vinylisonicotinonitrile) was purified by silica gel chromatography.

Reference： [1]Patent: WO2012/170845,2012,A2 .Location in patent: Page/Page column 80

7
[ 673-31-4 ]
[ 75927-49-0 ]
[ 1000376-26-0 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 5316 - 5319

8
[ 86845-28-5 ]
[ 75927-49-0 ]
[ 1432055-06-5 ]

Yield	Reaction Conditions	Operation in experiment
300 mg	With potassium phosphate; 1,1'-bis(di-tertbutylphosphino)ferrocene; palladium diacetate; In tetrahydrofuran; water; at 80℃; for 1.0h;Inert atmosphere;	1-ethenyl-3-methyl-5-(trifluoromethyl)benzene To <strong>[86845-28-5]1-bromo-3-methyl-5-(trifluoromethyl)benzene</strong> (500 mg, 2.51 mmol) was added THF (5 mL), aqueous tribasic potassium phosphate (2.0 M, 4.18 mL, 8.37 mmol), 2-ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (387 mg, 2.51 mmol), palladium(II) acetate (47 mg, 0.209 mmol), and 1,1'-bis(di-t-butylphosphino)ferrocene (99 mg, 0.209 mmol). The system was flushed with nitrogen gas and was heated at 80 C. for 1 hour. The reaction was filtered and then diluted with ethyl acetate and water. The organic layer was dried over sodium sulfate, filtered and concentrated. The crude product was purified by preparative TLC to yield 1-ethenyl-3-methyl-5-(trifluoromethyl)benzene (300 mg, 1.61 mmol). 1H NMR (500 MHz, CDCl3) delta7.47 (s, 1H), 7.40 (s, 1H), 7.34 (s, 1H), 6.76 (m, 1H), 5.85 (d, J=17.6 Hz, 1H), 2.43 (s, 1H).

Reference： [1]Patent: US2013/109649,2013,A1 .Location in patent: Paragraph 0220; 0221

9
[ 89892-22-8 ]
[ 75927-49-0 ]
[ 1305318-30-2 ]

Yield	Reaction Conditions	Operation in experiment
70.4%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; toluene; at 20 - 90℃;Sealed tube;	Synthesis of 7-vinylquinazoline [0574] To a stirred solution of <strong>[89892-22-8]7-bromoquinazoline</strong> (200 mg, 0.95 mmol) in Toluene: H20 (3 mL,(4:l)) was added 4,4,5,5-tetramethyl-2-vinyl-l,3,2- dioxaborolane (221 mg, 1.43 mmol), Na2CO3(304 mg,2.86 mmol),and Pd(PPh3)4 (55 mg,0.04 mmol) at RT. The reaction mixture was allowed to warm 90 °C stirred for 2h in seal tube. The reaction mixture was filtered, the solvent was evaporated, the crude material was purified by silica gel column chromatography to afford 7- vinylquinazoline (105 mg, 70.4percent) as a thick syrup. 1H-NMR (CDC13, 400 MHz): delta 9.31 (d, 2H), 7.95 (s, 1H), 7.86 (d, 1H), 6.98-6.85 (m, 1H), 6.05 (d, 1H), 5.55 (d, 1H); LC-MS: 98.77percent; 157.0 (M++l); (column; X-Bridge C-18, (50x3.0 mm, 3.5mu); RT 2.51 min. A: 5Mm NH4OAc in water, B: CH3CN, 0.8 ml/min); TLC: 30percent EtOAc/Hexane (Rf: 0.3).

Reference： [1]Patent: WO2013/142269,2013,A1 .Location in patent: Paragraph 0573; 0574

10
[ 22282-96-8 ]
[ 75927-49-0 ]
6-ethenyl-2-methyl-3-nitropyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; caesium carbonate; XPhos; In 2-methyltetrahydrofuran; water; at 60℃; for 1h;Inert atmosphere;	Intermediate 19: 6-ethenvl-2-methvl-3-nitrolvridineA suspension/solution of <strong>[22282-96-8]6-bromo-2-methyl-3-nitropyridine</strong> (500 mg, 2.304 mmol), 2-ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.782 mL, 4.61 mmol), palladium(II) acetate (25.9 mg,0.115 mmol), X-phos (110 mg, 0.230 mmol) and cesium carbonate (3.0 g, 9.22 mmol) in 2-methyltetrahydrofuran (2-MeTHF) (8 mL) and water (2 mL) was stirred under nitrogen at 60 C for1 hour. The reaction mixture was cooled then separated between ethyl acetate and water. Theorganic phase was washed with brine and dried over magnesium sulphate. The solvent was removed in vacuo and the residue was dissolved in DCM (5 mL). This was applied to a silica cartridge and eluted with a gradient of 0100% ethyl acetate in cyclohexane. This gave the crude product (440 mg) as a brown liquid which was used directly in the next step with no furtherpurification. LCMS (2 mm, formic) Rt 0.91 mi m/z (ESj 165 (M+H).1H NMR (400 MHz, CHLOROFORM-o) O ppm 8.28 (d, 1 H), 7.33 (d, 1 H), 6.85 (dd, 1 H), 6.40 (d, 1 H), 5.70 (d, 1 H), 2.89 (5, 3 H).
	With palladium diacetate; caesium carbonate; XPhos; In 2-methyltetrahydrofuran; water; at 60℃; for 1h;Inert atmosphere;	A suspension/solution of <strong>[22282-96-8]6-bromo-2-methyl-3-nitropyridine</strong> (500 mg, 2.304 mmol), 2-ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.782 mL, 4.61 mmol), palladium(II) acetate (25.9 mg, 0.115 mmol), X-phos (110 mg, 0.230 mmol) and cesium carbonate (3.0 g, 9.22 mmol) in 2-methyltetrahydrofuran (2-MeTHF) (8 mL) and water (2 mL) was stirred under nitrogen at 60 C. for 1 hour. The reaction mixture was cooled then separated between ethyl acetate and water. The organic phase was washed with brine and dried over magnesium sulphate. The solvent was removed in vacuo and the residue was dissolved in DCM (5 mL). This was applied to a silica cartridge and eluted with a gradient of 0-100% ethyl acetate in cyclohexane. This gave the crude product (440 mg) as a brown liquid which was used directly in the next step with no further purification. LCMS (2 min, formic) Rt 0.91 min, m/z (ES+) 165 (M+H). 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 8.28 (d, 1H), 7.33 (d, 1H), 6.85 (dd, 1H), 6.40 (d, 1H), 5.70 (d, 1H), 2.89 (s, 3H).

Reference： [1]Organic Letters,2015,vol. 17,p. 2214 - 2217
[2]Patent: WO2013/160419,2013,A1 .Location in patent: Page/Page column 33; 34
[3]Patent: US2015/65507,2015,A1 .Location in patent: Paragraph 0171; 0172

11
[ 16078-30-1 ]
[ 75927-49-0 ]
[ 1603838-20-5 ]

Reference： [1]Advanced Synthesis and Catalysis,2014,vol. 356,p. 929 - 933

12
[ 1749-68-4 ]
[ 75927-49-0 ]
[ 1609394-79-7 ]

Yield	Reaction Conditions	Operation in experiment
67%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; at 100℃; for 16.5h;Inert atmosphere; Sealed tube;	Step 1[00302j A mixture of <strong>[1749-68-4]6-chloro-2-methylpyrimidin-4-amine</strong> (300 mg, 2.09 mmol), 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (386 mg, 2.51 mmol) and sodiumcarbonate (886 mg, 8.36 mmol) in 1,4-dioxane (9.0 mL) and water (0.9 mL) was bubbled with argon with sonication for 1 mm. The mixture was treated with tetrakis(triphenylphosphine)palladium (169 mg, 0.146 mmol) and the vessel was sealed and subjected to 5 evacuate-fill cycles with argon. The mixture was stirred on a heating block at 100 C for 16.5 h, then was cooled to room temperature, diluted with water andextracted twice with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate and concentrated under vacuum. The residue was subjected to column chromatography (Isco Combiflash Companion, 24 g silica gel, 20-100% ethyl acetate-hexane, 8 mm, then isocratic) to provide 2-methyl-6-vinylpyrimidin-4-amine as a white solid (189 mg, 67% yield). Mass spectrum m/z 271, (2M+H). ?H NMR (400 MHz,DMSO-d6) oe 6.71 (br. s., 2H), 6.54 (dd, J=17.2, 10.6 Hz, 1H), 6.26 - 6.20 (m, 1H), 6.20 (s, 1H), 5.53 - 5.40 (m, 1H), 2.31 (s, 3H).

Reference： [1]Patent: WO2014/74661,2014,A1 .Location in patent: Paragraph 00302

13
[ 75927-49-0 ]
[ 320734-35-8 ]
7-vinylindolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane;Reflux; Inert atmosphere;	To a mixture of <strong>[320734-35-8]7-bromoindolin-2-one</strong> (10 g, 48 mmol) and sodium carbonate (10 g, 96 mmol) in 1,4-dioxane (100 mL) was added 4,4,5, 5-tetramethyl-2-vinyl-l ,3,2-dioxaborolane (7.3 g, 48 mmol) and Pd(PPh4)3 (2.5 g, 2.4 mmol) at room temperature. The mixture was heated to reflux and stirred under nitrogen overnight. On completion, the mixture was diluted with water (100 mL) and extracted with dichloromethane (3 x 200 mL). The combined organic layers were washed with brine (2 chi 200 mL), dried over anhydrous sodium sulfate, concentrated in vacuo and purified by silica gel column chromatography [petroleum ether: ethyl acetate = 6: 1 ] to give compound B-263 (6.8 g, 90% yield) as a yellow solid.

Reference： [1]Patent: WO2015/66371,2015,A1 .Location in patent: Paragraph 00522-00523

14
[ 40381-90-6 ]
[ 75927-49-0 ]
2-chloro-6-vinylnicotinonitrile [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 2214 - 2217

15
[ 452-92-6 ]
[ 75927-49-0 ]
5-ethenyl-2,4-difluoroaniline [ No CAS ]

Reference： [1]Patent: WO2016/31255,2016,A1 .Location in patent: Page/Page column 172

16
[ 75927-49-0 ]
[ 32779-37-6 ]
[ 883901-68-6 ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; water; at 90℃; for 12h;Inert atmosphere;	To a solution of 2, 5-dibromopyrimidine (2.0 g, 8.41 mmol), 4,4,5, 5-tetramethyl-2- vinyl-l,3,2-dioxaborolane (1.56 g, 10.09 mmol), and Pd(dppf)C12 (0.31 g, 0.42 mmol) in dioxane (20 mL) and water (2 mL) was added Na2CC>3 (1.782 g, 16.82 mmol) under N2. The resulting mixture was stirred at 90 C for 12 h. After cooling to RT, the mixture was diluted with water and extracted with EtOAc (100 mL x 3). The combined organic layers were dried over MgS04, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography (2-30% EtOAc in petroleum ether) to give the title compound as a oil. LRMS m/z (M+H) 185.1, 187.1 found, 185.1, 187.1 required.

Reference： [1]Patent: WO2016/100156,2016,A1 .Location in patent: Page/Page column 56; 57

17
[ 75927-49-0 ]
[ 131818-17-2 ]
[ 633327-37-4 ]

Reference： [1]New Journal of Chemistry,2017,vol. 41,p. 3172 - 3176

18
[ 6274-57-3 ]
[ 75927-49-0 ]
[ 1247001-30-4 ]

Reference： [1]New Journal of Chemistry,2017,vol. 41,p. 3172 - 3176

19
[ 75927-49-0 ]
[ 321436-06-0 ]
C₁₆H₂₀BNO₄ [ No CAS ]

Reference： [1]New Journal of Chemistry,2017,vol. 41,p. 3172 - 3176

20
[ 26163-07-5 ]
[ 75927-49-0 ]
(E)-N,N-dimethyl-5-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)pyridin-2-amine [ No CAS ]

Reference： [1]New Journal of Chemistry,2017,vol. 41,p. 3172 - 3176

21
[ 13534-90-2 ]
[ 75927-49-0 ]
[ 1255957-49-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In water; N,N-dimethyl-formamide; at 60℃;Inert atmosphere;	A mixture of compound 1 (237 mg, 1 mmol), 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (154 mg, 1 mmol), aq. K3PO4 (3 mL, 1 M, 3 mmol) and Pd(dppf)Cl2 (73 mg, 0.1 mmol) in DMF (10 mL) was stirred at 60 C under N2 for 3 h. The reaction mixture was diluted with H2O and extracted with EA. The organic layer was washed with H2O, brine, dried over Na2SO4. After concentrated, the residue was purified by silica gel column chromatography (PE : EA = 30:1) to give the product of compound 2 (170 mg, yield: 92 %). 1H-NMR (CDCl3, 400 MHz) d 8.70 (s, 1H), 8.45 (d, J = 7.2Hz, 1H), 7.41 (d, J = 7.2Hz, 1H), 6.98 (q, J = 6.8Hz, 1H), 5.94 (d, J = 17.6Hz, 1H), 5.60 (d, J = 11.2Hz, 1H).

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 1373 - 1375

22
[ 3066-75-9 ]
[ 1214264-88-6 ]
[ 75927-49-0 ]
(R)-2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pent-4-en-1-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine [ No CAS ]