[ CAS No. 1009303-77-8 ] {[proInfo.proName]}

Name: 1009303-77-8|2-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenemethanol|97%
Brand: Ambeed
SKU: A357377
Price: 6.0 USD
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Quality Control of [ 1009303-77-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1009303-77-8 ]

SDS Specification

Alternatived Products of [ 1009303-77-8 ]

Product Details of [ 1009303-77-8 ]

CAS No. :	1009303-77-8	MDL No. :	MFCD13184694
Formula :	C₁₄H₂₁BO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WBEPVYJQWVRDSC-UHFFFAOYSA-N
M.W :	264.13	Pubchem ID :	56845242
Synonyms :

Calculated chemistry of [ 1009303-77-8 ]

Physicochemical Properties

Num. heavy atoms :	19
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.57
Num. rotatable bonds :	3
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	75.54
TPSA :	47.92 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 :	No
Log Kp (skin permeation) :	-6.5 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.99
Log Po/w (WLOGP) :	1.33
Log Po/w (MLOGP) :	0.82
Log Po/w (SILICOS-IT) :	1.75
Consensus Log Po/w :	1.18

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.77
Solubility :	0.452 mg/ml ; 0.00171 mol/l
Class :	Soluble
Log S (Ali) :	-2.62
Solubility :	0.63 mg/ml ; 0.00238 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.96
Solubility :	0.0292 mg/ml ; 0.000111 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	3.01

Safety of [ 1009303-77-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1009303-77-8 ]

* 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 [ 1009303-77-8 ]
Downstream synthetic route of [ 1009303-77-8 ]

[ 1009303-77-8 ] Synthesis Path-Upstream 1~1

1
[ 80866-82-6 ]
[ 73183-34-3 ]
[ 1009303-77-8 ]

Reference： [1] Patent: WO2007/80382, 2007, A1, . Location in patent: Page/Page column 131

[ 1009303-77-8 ] Synthesis Path-Downstream 1~16

1
[ 1009303-44-9 ]
[ 1009303-77-8 ]
AZD₈₀₅₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; at 140.0℃; for 0.5h;Microwave radiation;	The appropriate chloro-substrate (1 equiv) was dissolved in a toluene/ethanol (1:1) solution (0.02 M). Sodium carbonate (2 equiv) and the appropriate pinacolate boron ester or boronic acid (1 equiv) were then added followed by tetrakis(triphenylphosphine) palladium0 (0.1 equiv). The reaction vessel was sealed and the mixture exposed to microwave radiation (140 0C, medium absorption setting) for 30 minutes. Upon completion the samples were filtered through a silica cartridge, washed with EtOAc and then concentrated in vacuo. The crude residue was then purified by preparative HPLC to give the desired products.

Reference： [1]Patent: WO2008/23161,2008,A1 .Location in patent: Page/Page column 122; 128
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1212 - 1216

2
[ 80866-82-6 ]
[ 73183-34-3 ]
[ 1009303-77-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80.0℃; for 3.0h;	Example 89:[2-Methoxy-5-[4-(methylsulfonylmethyl)-6-morpholin-4-yI-pyrimidin-2- yl] phenyl] methanolA mixture of 5-bromo-2-methoxybenzylalcohol (250 mg), potassium acetate (339 mg) and bis(pinacolato)diboron (352 mg) in 1,4-dioxane (10 mL) was degassed for 5 minutes. 1,1'- Bis(diphenylphosphino)fe?Ocenedichloropalladium(II) dichloromethane adduct (57 mg) was added and the reaction was heated to 8O0C for 3 hours. 2-Chloro-4~ (methylsulfonylmethyl)-6-morpholin-4-yl-pyrimidine (337 mg), ethanol (0.75 mL), a 2M solution of sodium carbonate (2.7 mL) and additional 1,1'- bis(diphenylphosphino)ferrocenedichloropalladium(II) dichloromethane adduct (57 mg) were added and the heating was continued for a further 66 hours. The reaction mixture was cooled and concentrated in vacuo. The residue was partitioned between ethyl acetate (50 mL) and water (50 mL) and filtered. The organic phase was dried (MgSO4), concentrated in vacuo and chromatographed on silica, eluting with 5% methanol in DCM. The chromatography was repeated and the residue triturated with diethyl ether to give the desired compound as a white solid (158 mg). Mass Spectrum; MH+ 394 NMR Spectrum: 1H NMR (DMSOd6) delta3.23 (3H, s), 3.73 - 3.74 (8H, m), 3.84 (3H, d), 4.51 (2H, s), 4.54 (2H, d), 5.08 (IH, t), 6.83 (IH, s), 7.00 - 7.06 (IH, m), 8.23 - 8.26 (IH, m), 8.41 (IH, d)

Reference： [1]Patent: WO2007/80382,2007,A1 .Location in patent: Page/Page column 131

3
[ 944058-89-3 ]
[ 1009303-77-8 ]
[2-methoxy-5-[4-(methylsulfonylmethyl)-6-morpholin-4-yl-pyrimidin-2-yl]phenyl]methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; ethanol; water; for 66.0h;Heating / reflux;	Example 89:[2-Methoxy-5-[4-(methylsulfonylmethyl)-6-morpholin-4-yI-pyrimidin-2- yl] phenyl] methanolA mixture of 5-bromo-2-methoxybenzylalcohol (250 mg), potassium acetate (339 mg) and bis(pinacolato)diboron (352 mg) in 1,4-dioxane (10 mL) was degassed for 5 minutes. 1,1'- Bis(diphenylphosphino)fe?Ocenedichloropalladium(II) dichloromethane adduct (57 mg) was added and the reaction was heated to 8O0C for 3 hours. 2-Chloro-4~ (methylsulfonylmethyl)-6-morpholin-4-yl-pyrimidine (337 mg), ethanol (0.75 mL), a 2M solution of sodium carbonate (2.7 mL) and additional 1,1'- bis(diphenylphosphino)ferrocenedichloropalladium(II) dichloromethane adduct (57 mg) were added and the heating was continued for a further 66 hours. The reaction mixture was cooled and concentrated in vacuo. The residue was partitioned between ethyl acetate (50 mL) and water (50 mL) and filtered. The organic phase was dried (MgSO4), concentrated in vacuo and chromatographed on silica, eluting with 5% methanol in DCM. The chromatography was repeated and the residue triturated with diethyl ether to give the desired compound as a white solid (158 mg). Mass Spectrum; MH+ 394 NMR Spectrum: 1H NMR (DMSOd6) delta3.23 (3H, s), 3.73 - 3.74 (8H, m), 3.84 (3H, d), 4.51 (2H, s), 4.54 (2H, d), 5.08 (IH, t), 6.83 (IH, s), 7.00 - 7.06 (IH, m), 8.23 - 8.26 (IH, m), 8.41 (IH, d)

Reference： [1]Patent: WO2007/80382,2007,A1 .Location in patent: Page/Page column 131

Yield	Reaction Conditions	Operation in experiment
81%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 100.0℃; for 14.0h;Inert atmosphere;	General procedure: A mixture of 2-(3-Bromo-phenoxy)-ethanol (6 g, 27.64 mmol), 4 bis(pinacolato)diboron (7.7 g, 30.40 mmol) and potassium acetate (5.4 g, 55.2 mmol) in 1 ,4-dioxane (50 ml_) was degassed with nitrogen for 20 min before the addition of 1 ,1'- Bis(diphenylphosphino)ferrocene]dichloropalladium(ll).CH2Cl2 (1.01 g, 1.38 mmol). The reaction mixture was then heated at 100C for 14 h. It was filtered through a celite pad. The pad was extensively washed with dichloromethane/methanol and the filtrate was concentrated under reduced pressure. Purification by flash column chromatography on silica of the crude afforded the title compound as a brown solid (3.0 g, 42%). 1H NMR (400 MHz, DMSO-d6): delta 7.23 (t, J = 8.08 Hz, 1 H), 7.14-7.09 (m, 2H), 6.95 (dd, J = 8.08, 2.28 Hz, 1H), 4.85-4.82 (m, 1H), 3.98-3.93 (m, 2H), 3.71-3.67 (m, 2H), 1.28 (s, 9H). LC/MS: (Method A) 265.3 (M+H), RT. 2.8 min, 72.0% (Max).

5
[ 938443-23-3 ]
[ 1009303-77-8 ]
KU-63794 [ No CAS ]