[ CAS No. 741709-63-7 ]

Name: 741709-63-7|5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile|97%
Brand: Ambeed
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Quality Control of [ 741709-63-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 741709-63-7 ]

SDS Specification

Alternatived Products of [ 741709-63-7 ]

Product Details of [ 741709-63-7 ]

CAS No. :	741709-63-7	MDL No. :	MFCD06657825
Formula :	C₁₂H₁₅BN₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IXTBQKLZPOYJFJ-UHFFFAOYSA-N
M.W :	230.07	Pubchem ID :	16414188
Synonyms :

Calculated chemistry of [ 741709-63-7 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.5
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	65.43
TPSA :	55.14 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.36 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.89
Log Po/w (WLOGP) :	1.25
Log Po/w (MLOGP) :	-0.08
Log Po/w (SILICOS-IT) :	1.3
Consensus Log Po/w :	0.87

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.65
Solubility :	0.512 mg/ml ; 0.00223 mol/l
Class :	Soluble
Log S (Ali) :	-2.67
Solubility :	0.491 mg/ml ; 0.00214 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.72
Solubility :	0.044 mg/ml ; 0.000191 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.96

Safety of [ 741709-63-7 ]

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

Application In Synthesis of [ 741709-63-7 ]

* 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.

Upstream synthesis route of [ 741709-63-7 ]
Downstream synthetic route of [ 741709-63-7 ]

[ 741709-63-7 ] Synthesis Path-Upstream 1~2

1
[ 97483-77-7 ]
[ 73183-34-3 ]
[ 741709-63-7 ]

Yield	Reaction Conditions	Operation in experiment
46%	With potassium acetate In dimethyl sulfoxide at 20 - 80℃; for 96 h;	5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine-2-carbonitrile Into a 250 mL RBF was added 3.0 g 5-Bromo-pyridine-2-carbonitrile (3.0 g, 16.39 mmol), Bis(pinacolato)diboron (4.58 g, 18.03 mmol), KOAc (5.47 g, 55.74 mmol), and DMSO (100 mL). After degassing for 20 minutes, PdCl₂dppf-CH₂Cl₂ (1.39 g, 1.64 mmol) was added and the solution was stirred for 24 hours at 80° C., and then room temperature for 3 days. 50 mL water was added and the product was extracted with ethyl acetate. The combined organics were washed with brine, dried over Na₂SO₄ and concentrated. The dark-colored residue was purified by FCC eluding with 20percent acetone/hexanes to give a red solid. The solid was triturated with hexane to give 1.72 g (46percent) Int-26 as a light-pink solid. Into a 250 mL round-bottomed flask was added 3.0 g of 5-bromo-pyridine-2-carbonitrile (3.0 g, 16.39 mmol), bis(piniacolato)diboron (4.58 g, 18.03 mmol), KOAc (5.47 g, 55.74 mmol), and DMSO (100 mL). After degassing for 20 minutes, PdCl₂dppf-CH₂Cl₂(1.39 g, 1.64 mmol) was added and the solution was stirred for 24 hours at 80° C., and then at room temperature for 3 days. 50 mL water was added and the product was extracted with ethyl acetate. The combined organics were washed with brine, dried over Na₂SO₄and concentrated. The dark-colored residue was purified by flash column chromatography eluting with 20percent acetone/hexanes to give a red solid. The solid was triturated with hexane to give 1.72 g (46percent) of I-238 as a light-pink solid.
24%	With potassium acetate; palladium diacetate; triphenylphosphine In N,N-dimethyl-formamide at 80℃; Inert atmosphere	[0450] To a solution of5-bromopicolinonitrile (1.00 g, 5.46mmol) in DMF (10 mL) was added 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (2.77 g, 10.9 mmol),Pd(OAc)2 (61.0mg, 0.273 mmol), PPh3 (285 mg, 1.09 mmol)and KOAc (1.61 g, 16.4 mol) under a nitrogen atmosphere.The resulting mixture was stirred at 80° C. overnight. Thereaction mixture was cooled tort and the solids were removedby filtration. The filtrate was concentrated under reducedpressure to obtain a residue, which was purified by flashcolunm chromatography on silica gel with EtOAc/petroleumether (1 :50 v/v) to obtain compound 1f as a white solid (300mg, 24percent yield). Mass Spectrum (LCMS, ESI pos.): Calcd.for C12H15BN20 2 : 231.1 (M+H). found: 231.1.

Reference： [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 13, p. 5473 - 5494
[2] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 5, p. 1277 - 1281
[3] Patent: US2009/136473, 2009, A1, . Location in patent: Page/Page column 36; 61
[4] Patent: US2014/364414, 2014, A1, . Location in patent: Paragraph 0438; 0449-0450
[5] Patent: WO2009/74812, 2009, A1, . Location in patent: Page/Page column 70

2
[ 31181-90-5 ]
[ 741709-63-7 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 5, p. 1277 - 1281

[ 741709-63-7 ] Synthesis Path-Downstream 1~68

1
[ 741709-63-7 ]
[ 880495-82-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1277 - 1281

2
[ 97483-77-7 ]
[ 73183-34-3 ]
[ 741709-63-7 ]

Yield	Reaction Conditions	Operation in experiment
46%	With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In dimethyl sulfoxide; at 20 - 80℃; for 96h;Product distribution / selectivity;	5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine-2-carbonitrile Into a 250 mL RBF was added 3.0 g 5-Bromo-pyridine-2-carbonitrile (3.0 g, 16.39 mmol), Bis(pinacolato)diboron (4.58 g, 18.03 mmol), KOAc (5.47 g, 55.74 mmol), and DMSO (100 mL). After degassing for 20 minutes, PdCl2dppf-CH2Cl2 (1.39 g, 1.64 mmol) was added and the solution was stirred for 24 hours at 80 C., and then room temperature for 3 days. 50 mL water was added and the product was extracted with ethyl acetate. The combined organics were washed with brine, dried over Na2SO4 and concentrated. The dark-colored residue was purified by FCC eluding with 20% acetone/hexanes to give a red solid. The solid was triturated with hexane to give 1.72 g (46%) Int-26 as a light-pink solid. Into a 250 mL round-bottomed flask was added 3.0 g of 5-bromo-pyridine-2-carbonitrile (3.0 g, 16.39 mmol), bis(piniacolato)diboron (4.58 g, 18.03 mmol), KOAc (5.47 g, 55.74 mmol), and DMSO (100 mL). After degassing for 20 minutes, PdCl2dppf-CH2Cl2 (1.39 g, 1.64 mmol) was added and the solution was stirred for 24 hours at 80 C., and then at room temperature for 3 days. 50 mL water was added and the product was extracted with ethyl acetate. The combined organics were washed with brine, dried over Na2SO4 and concentrated. The dark-colored residue was purified by flash column chromatography eluting with 20% acetone/hexanes to give a red solid. The solid was triturated with hexane to give 1.72 g (46%) of I-238 as a light-pink solid.
24%	With potassium acetate; palladium diacetate; triphenylphosphine; In N,N-dimethyl-formamide; at 80℃;Inert atmosphere;	[0450] To a solution of5-bromopicolinonitrile (1.00 g, 5.46mmol) in DMF (10 mL) was added 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (2.77 g, 10.9 mmol),Pd(OAc)2 (61.0mg, 0.273 mmol), PPh3 (285 mg, 1.09 mmol)and KOAc (1.61 g, 16.4 mol) under a nitrogen atmosphere.The resulting mixture was stirred at 80 C. overnight. Thereaction mixture was cooled tort and the solids were removedby filtration. The filtrate was concentrated under reducedpressure to obtain a residue, which was purified by flashcolunm chromatography on silica gel with EtOAc/petroleumether (1 :50 v/v) to obtain compound 1f as a white solid (300mg, 24% yield). Mass Spectrum (LCMS, ESI pos.): Calcd.for C12H15BN20 2 : 231.1 (M+H). found: 231.1.
		A solution of 5-bromo-2-cyanopyridine (0.50 g, 2.73 mmol), bispinacolatodiboron (0.76 g, 3.0 mmol) and KOAc (0.34 g, 4.10 mmol) in 1 ,4-dioxane (10.0 mL) was degassed by flushing with nitrogen for 15 min. Tricyclohexylphosphine (0.091 g, 0.33 mmol) and tris(dibenzyledineacetone) dipalladium (0) (0.14 g, 0.14 mmol) was then added to the reaction mixture, which was again degassed by nitrogen for 15 min. The resulting reaction mixture was heated to 1000C for 2 h. After the completion of the reaction (TLC monitoring), the reaction mixture was filtered through celite bed and the filtrate was concentrated to get the crude residue that was carried forward to the next step without further purification. MS: 231.10 (M+H)+.

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 5473 - 5494
[2]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1277 - 1281
[3]Patent: US2009/136473,2009,A1 .Location in patent: Page/Page column 36; 61
[4]Patent: US2014/364414,2014,A1 .Location in patent: Paragraph 0438; 0449-0450
[5]Patent: WO2009/74812,2009,A1 .Location in patent: Page/Page column 70
[6]Journal of Medicinal Chemistry,2018,vol. 61,p. 10875 - 10894

3
[ 741709-63-7 ]
[ 954123-89-8 ]
[ 954123-95-6 ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium hydroxide;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; at 120℃; for 1h;Sealed tube; Microwave irradiation;	tert-Butyl 4-((5-(6-cyanopyridin-3-yl)-2-methoxybenzyloxy)methyl)-4-phenylpiperidine-1-carboxylate. A microwave tube was charged with tert-butyl 4-((5-bromo-2-methoxybenzyloxy)methyl)-4-phenylpiperidine-1-carboxylate (50 mg, 0.102 mmol), <strong>[741709-63-7]5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile</strong> (94 mg, 0.408 mmol), and tetrakis(triphenylphosphine)-palladium(0) (11.78 mg, 10.20 mumol). The tube was flushed with nitrogen, treated with tetrahydrofuran (2 mL) and potassium hydroxide (1 M in water, 0.41 mL, 0.41 mmol). The tube was sealed and heated at 120 C. for 1 h via microwave. The reaction was cooled, poured into ether, washed with water (2×), then brine, dried over magnesium sulfate, and concentrated. Column chromatography (ethyl acetate/hexanes) gave 46 mg (88%) as a colorless oil. 1H NMR (500 MHz, CDCl3) delta ppm 8.80 (d, J=2.1 Hz, 1H), 7.80 (dd, J=7.9, 2.1 Hz, 1H), 7.72 (d, J=8.2 Hz, 1H), 7.44 (dd, J=8.5, 2.4 Hz, 1H), 7.37 (m, 2H), 7.31 (m, 3H), 7.20 (m, 1H), 6.92 (d, J=8.5 Hz, 1H), 4.47 (s, 2H), 3.83 (s, 3H), 3.73 (m, 2H), 3.50 (s, 2H), 3.06 (m, 2H), 2.20 (m, 2H), 1.89 (m, 2H), 1.42 (s, 9H); 13C NMR (126 MHz, CDCl3) delta ppm 157.8, 155.1, 149.3, 143.2, 139.6, 134.1, 131.5, 128.7, 128.5, 128.4, 127.9, 127.3, 127.1, 126.6, 126.4, 117.6, 110.9, 102.9, 79.9, 79.4, 67.7, 55.6, 41.8, 40.3, 32.2, 28.6. Mass spec.: 514.45 (MH)+.

Reference： [1]Patent: US2007/249607,2007,A1 .Location in patent: Page/Page column 74

4
[ 741709-63-7 ]
[ 955885-20-8 ]
[ 955882-64-1 ]

Yield	Reaction Conditions	Operation in experiment
46%	With triethylamine;copper diacetate; In dichloromethane; at 20℃; for 96h;Molecular sieve;	Example 181; 4-(6-Cyano-pyridin-3-yloxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide; A mixture of <strong>[741709-63-7]5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile</strong> (634 mg, 2.76 mmol), 4-hydroxy-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide (31a) (396 mg, 1.33 mmol), Et3N (0.96 mL, 6.89 mmol), and Cu(OAc)2 (501 mg, 2.76 mmol) in CH2Cl2 (15 mL) was stirred at room temperature with 4A molecular sieves for 4 days, then filtered through celite, washed with CHCl3, concentrated, and purified by column chromatography with 30-60% EtOAc in hexanes to give a white foam (246 mg, 46% yield). 1H NMR (400 MHz, CDCl3) delta 9.23 (s, 1H) 8.45 (d, J=2.53 Hz, 1H) 7.65 (d, J=8.59 Hz, 1H) 7.21-7.35 (m, 2H) 7.10 (d, J=111.37 Hz, 2H) 6.78 (d, J=2.02 Hz, 1H) 3.73 (s, 3H) 2.89 (s, 2H)) 1.48 (s, 6H); LCMS for C21H19N5O3 m/z 390.00 (M+H+).
46%	With copper diacetate; triethylamine; In dichloromethane; at 20℃; for 96h;Molecular sieve;	Example 181:; 4-(6-Cyano-pyridin-3-yloxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1- methyl-1 tf-pyrazol-3-yl)-amide; A mixture of <strong>[741709-63-7]5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile</strong> (634 mg, 2.76 mmol), 4-hydroxy- 2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyI-1H-pyrazol-3-yl)-amide (31a) (396 mg, 1.33 mmol), Et3N (0.96 mL, 6.89 mmol), and Cu(OAc)2 (501 mg, 2.76 mmol) in CH2CI2 (15 mL) was stirred at room temperature with 4A molecular sieves for 4 days, then filtered through celite, washed with CHCI3, concentrated, and purified by column chromatography with 30-60% EtOAc in hexanes to give a white foam (246 mg, 46% yield). 1H NMR (400 MHz, CDCI3) delta 9.23 (s, 1 H) 8.45 (d, J=2.53 Hz, 1 H) 7.65 (d, J=8.59 Hz, 1 H) 7.21 - 7.35 (m, 2 H) 7.10 (d, J=11.37 Hz, 2 H) 6.78 (d, J=2.02 Hz, 1 H) 3.73 (s, 3 H) 2.89 (s, 2 H) ) 1.48 (s, 6 H); LCMS for C21H19N5O3 m/z 390.00 (M+H+).

Reference： [1]Patent: US2008/280875,2008,A1 .Location in patent: Page/Page column 95
[2]Patent: WO2007/122482,2007,A1 .Location in patent: Page/Page column 125

5
[ 741709-63-7 ]
[ 862730-04-9 ]
5-(4-amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)pyridine-2-carbonitrile [ No CAS ]