[ CAS No. 259209-17-1 ]

Name: 259209-17-1|(2-Hydroxy-3-methoxyphenyl)boronic acid|96%
Brand: Ambeed
SKU: A194458
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Quality Control of [ 259209-17-1 ]

COA NMR CNMR HPLC LC-MS

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Alternatived Products of [ 259209-17-1 ]

Product Details of [ 259209-17-1 ]

CAS No. :	259209-17-1	MDL No. :	MFCD08689552
Formula :	C₇H₉BO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	167.96 g/mol	Pubchem ID :	-
Synonyms :

Calculated chemistry of of [ 259209-17-1 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	3.0
Molar Refractivity :	44.78
TPSA :	69.92 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.62 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.99
Log Po/w (WLOGP) :	-0.92
Log Po/w (MLOGP) :	-0.59
Log Po/w (SILICOS-IT) :	-1.22
Consensus Log Po/w :	-0.35

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.74
Solubility :	3.04 mg/ml ; 0.0181 mol/l
Class :	Very soluble
Log S (Ali) :	-2.05
Solubility :	1.51 mg/ml ; 0.00898 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-0.83
Solubility :	24.6 mg/ml ; 0.147 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.04

Safety of [ 259209-17-1 ]

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

Application In Synthesis of [ 259209-17-1 ]

* 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 [ 259209-17-1 ]

[ 259209-17-1 ] Synthesis Path-Downstream 1~33

1
[ 259209-52-4 ]
[ 259209-17-1 ]
6-(2-Hydroxy-3-methoxyphenyl)-6'-(2-hydroxy-4-methylphenyl)-2,2'-bipyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%		II.50 50 50 Prepration of 6-(2-Hydroxy-3-methoxyphenyl)-6'-(2-hydroxy-4-methylphenyl)-2,2'-bipyridine 6-(2-Hydroxy-3-methoxyphenyl)-6'-(2-hydroxy-4-methylphenyl)-2,2'-bipyridine was prepared from 6-bromo-6'-(2-hydroxy-4-methylphenyl)-2,2'-bipyridine and 2-hydroxy-3-methoxyphenylboronic acid in 33% yield using method F; δH [2H6]-DMSO 13.52,(2H, b), 8.31,(2H, dd), 8.26,(1H, d), 8.21,(1H, d), 8.12,(1H, d), 8.02,(1H, d), 7.70,(1H, d), 7.09,(1H, d), 6.92, (1H, t), 6.82,(1H, d), 3.86,(3H, s), 2.32,(3H, s); MS 385 (MH)+; HPLC retention time (system 1) 4.21 minutes.

Reference： [1]Current Patent Assignee: MINDSET RX INC - US6177419, 2001, B1

2
[ 259209-17-1 ]
[ 1272672-24-8 ]
[ 1272672-25-9 ]

Yield	Reaction Conditions	Operation in experiment
28.3%	With caesium carbonate In 1,4-dioxane; water at 160℃; for 0.666667h; microwave reactor;	24 To a solution of 1 -(4-bromophenyl)-2-chloro-7-hydroxy-5-oxo-4,5-dihydro-1 H- pyrrolo[3,2-b]pyridine-6-carbonitrile (Example 23) (150 mg, 0.41 1 mmol) in 1 ,4- dioxane (5 mL)/ water (3 ml.) were added [2-hydroxy-3-(methyloxy)phenyl]boronic acid (83 mg, 0.494 mmol), cesium carbonate (402 mg, 1.234 mmol) and Pd(PPh3)4 (1.0 mg, 1 .234 μηηοΙ). The reaction vessel was sealed and heated to 160 °C for 20 min in a microwave reactor. To complete the reaction, [2-hydroxy-3- (methyloxy)phenyl]boronic acid (83 mg, 0.494 mmol) and Pd(PPh3)4 (1.0 mg, 1.234 μηηοΙ) were added again and the reaction vessel was sealed and heated to 160 °C for 20 min in microwave reactor. After cooling, the reaction mixture was extracted, and the organic layer was washed with 1 N HCI solution and evaporated off. The residue was dissolved with a hot MeOH /CH3CN (80/20) mixture and treated with charcoal filtered. The filtrate was crystallined to give the product 2-chloro-7-hydroxy-1-[2'- hydroxy-3'-(methyloxy)-4-biphenylyl]-5-oxo-4,5-dihydro-1 H-pyrrolo[3,2-b]pyridine-6- carbonitrile (50 mg, 0.1 16 mmol, 28.3 % yield) as a white powder. 1H NMR: (DMSO- d6, 300MHz) δ 9.74 (br s, 1 H), 8.71 (s, 1 H), 7.56 (d, J = 8.4 Hz, 2H), 7.23 (d, J = 8.4 Hz, 2H), 7.02-6.84 (m, 3H), 5.94 (s, 1 H), 3.86 (s, 3H). LCMS: (M+H)+ : 408; Rt: 2.63 min. HRMS: calculated for C2iH15CIN304 (M+H)+ : 408.0751 ; found: 408.0765; Rt: 2.34 min.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2011/29855, 2011, A1 Location in patent: Page/Page column 118

3
[ 259209-17-1 ]
[ 1346608-15-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: caesium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 2 h / Reflux 2.1: dichloromethane / 3 h / 20 °C 2.2: 80 °C