[ CAS No. 480424-49-5 ] {[proInfo.proName]}

Name: 480424-49-5|3-Formyl-2-methoxyphenylboronic acid|95%
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Quality Control of [ 480424-49-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 480424-49-5 ]

SDS Specification

Alternatived Products of [ 480424-49-5 ]

Product Details of [ 480424-49-5 ]

CAS No. :	480424-49-5	MDL No. :	MFCD08689486
Formula :	C₈H₉BO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DUROSIJIMLRFHR-UHFFFAOYSA-N
M.W :	179.97	Pubchem ID :	16218167
Synonyms :

Calculated chemistry of [ 480424-49-5 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	3
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	48.15
TPSA :	66.76 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 :	No
Log Kp (skin permeation) :	-7.21 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.26
Log Po/w (WLOGP) :	-0.81
Log Po/w (MLOGP) :	-0.61
Log Po/w (SILICOS-IT) :	-0.58
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) :	-1.26
Solubility :	9.82 mg/ml ; 0.0546 mol/l
Class :	Very soluble
Log S (Ali) :	-1.22
Solubility :	10.8 mg/ml ; 0.0598 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.36
Solubility :	7.8 mg/ml ; 0.0434 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.77

Safety of [ 480424-49-5 ]

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

Application In Synthesis of [ 480424-49-5 ]

* 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 [ 480424-49-5 ]

[ 480424-49-5 ] Synthesis Path-Downstream 1~16

1
[ 494799-19-8 ]
[ 480424-49-5 ]
[ 1104194-72-0 ]

Yield	Reaction Conditions	Operation in experiment
77%	With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; water; at 110.0℃; for 2.0h;	Methyl 2-bromo-3-cyclohexyl-lH-indole-6-carboxylate (prepared as in International patent application WO 2004/087714), (3-formyl-2-methoxyphenyl) boronic acid (1.5 eq) and Pd(PPh3)2Cl2 (0.1 eq) were dissolved in dioxane (0.08M). The solution was degassed and flushed with Ar. 2M Na2CO3 solution (1 eq) was added and the mixture was heated to 110 0C for 2 h. All volatiles were evaporated in vacuo and the residual material was dissolved in EtOAc, filtered over Celite and evaporated in vacuo. The residual material was filtered over a plug of silica gel eluting with (PE/EtOAc 1:1). After evaporation of the fractions containing product and trituration with Et2O methyl 3-cyclohexyl-2-(3-formyl-2-methoxyphenyl)-lH-indole-6- <n="78"/>carboxylate was obtained as off-white solid (77%). 1R NMR (400 MHz, DMSO-J6) delta 1.16-1.39 (m, 3H), 1.51-1.97 (m, 7H), 2.59-2.67 (m, IH), 3.47 (s, 3H), 3.85 (s, 3H), 7.40-7.45 (m, IH), 7.61 (d, J8.4, IH), 7.68 (d, J 7.4, IH), 7.85 (d, J 8.4, 2H), 8.00 (s, IH), 10.39 (s, IH), 11.55 (s, IH); (ES+) m/z 392 (M+H)+.
77%	With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; water; at 110.0℃; for 2.0h;Inert atmosphere;	Methyl 2-bromo-3-cyclohexyl-lH-indole-6-carboxylate (prepared as in International patent application WO 2004/087714), (3-formyl-2-methoxyphenyl) boronic acid (1.5 eq) and Pd(PPlIs)2Cl2 (0.1 eq) were dissolved in dioxane (0.08M). The solution was degassed and flushed with Ar. An aq. solution of Na2CO3 solution (2 M, 1 eq) was added and the mixture was heated to 110 0C for 2 h. All volatiles were evaporated in vacuo and the residual material was dissolved in EtOAc, filtered over Celite and evaporated in vacuo. The residual material was filtered over a plug of silica gel eluting with (PE/EtOAc 1 :1). After evaporation of the fractions containing product and trituration with Et2O the title compound was obtained as an off-white solid (77%). (ES+) m/z 392 (M+Eta)+.

Reference： [1]Patent: WO2009/10783,2009,A1 .Location in patent: Page/Page column 76-77
[2]Patent: WO2010/82050,2010,A1 .Location in patent: Page/Page column 26

2
[ 930288-42-9 ]
[ 480424-49-5 ]
[ 930292-90-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 766 - 769

3
[ 480424-49-5 ]
N-((1s,4s)-4-(1,5-dimethyl-1H-pyrazole-3-carboxamido)cyclohexyl)-5-fluoro-2-(3-iodophenoxy)nicotinamide [ No CAS ]
N-((1s,4s)-4-(1,5-dimethyl-1H-pyrazole-3-carboxamido)cyclohexyl)-5-fluoro-2-(3'-formyl-2'-methoxybiphenyl-3-yloxy)nicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; In water; acetonitrile; at 70.0℃; for 1.0h;	Example 106N-((ls,4s)-4-(l,5-dimethyl-lH-pyrazole-3-carboxamido)cyclohexyl)-2-(3'-(((3S,5R)-3,5- dimethylpiperazin-l-yl)methyl)-2'-methoxybiphenyl-3-yloxy)-5-fluoronicotinamide Step (a) N-((ls,4s)-4-(l,5-dimethyl-lH-pyrazole-3-carboxamido)cyclohexyl)-5-fluoro-2- (3 '-for myl-2'-methoxybiphenyl-3-yloxy) nicotinamideA solution of potassium carbonate (0.215 g, 1.56 mmol) in water (5 mL), N-((ls,4s)-4-(l,5- dimethyl-lH-pyrazole-3-carboxamido)cyclohexyl)-5-fluoro-2-(3-iodophenoxy)nicotinamide (0.3 g, 0.52 mmol) and <strong>[480424-49-5]3-formyl-2-methoxyphenylboronic acid</strong> (0.112 g, 0.62 mmol) were added sequentially to a stirred solution of palladium(II) acetate (0.012 g, 0.05 mmol) and S- Phos (0.042 g, 0.10 mmol) in acetonitrile (7 mL) and heated at 70 0C for 1 h. The mixture was cooled to RT, extracted with EtOAc, washed with water and brine, dried (MgSO4), filtered <n="172"/>and evaporated in vacuo. The residue was purified by chromatography on silica with 40 %EtOAc/isohexane as eluent to give the sub-title compound as a brown foam. Yield: 290 mg1H NMR (300 MHz, CDCl3) delta 10.36 (s, IH), 8.38 (m, IH), 8.08 (m, 2H), 7.84 (m, 2H), 7.63(m, IH), 7.58 (t, J= 8.0 Hz, IH), 7.49 (m, 2H), 7.24 (m, IH), 6.66 (d, J= 8.3 Hz, IH), 6.51(s, IH), 4.24 (m, IH), 4.04 (m, IH), 3.69 (s, 3H), 3.55 (s, 3H), 2.27 (s, 3H), 1.98 - 1.81 (m,8H).MS: APCI (+ve):586 (M+l).

Reference： [1]Patent: WO2009/144494,2009,A1 .Location in patent: Page/Page column 170-171

4
[ 480424-49-5 ]
[ 1128268-00-7 ]
[ 1240969-79-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;trans-bis(triphenylphosphine)palladium dichloride; In water; acetonitrile; at 70.0℃; for 3.0h;Inert atmosphere;	Example 7; Step A. Ethyl 1-[6-(3-formyl-2-methoxyphenyl)pyridin-2-yl]-5-(trifluoromethyl)-1H-pyrazole-4-carboxylateTo a flask containing the title compound from the Example 1 Step D (1.65 g, 5.16 mmol) were added <strong>[480424-49-5](3-formyl-2-methoxyphenyl)boronic acid</strong> (1.02 g, 5.68 mmol) and trans-dichlorobis(triphenylphosphine)palladium (II) (0.36 g, 0.52 mmol). Acetonitrile (26 mL) and sodium carbonate (12.90 mL, 1.0 M aqueous, 12.90 mmol) were added, and the resulting mixture was degassed via nitrogen sparge. The reaction mixture was stirred at 70 C. for 3 h, then was allowed to cool to ambient temperature and was poured into water. The mixture was extracted with EtOAc, and the organic phase was concentrated in vacuo. Purification by chromatography on silica gel (0 to 30% EtOAc in hexanes, then 30 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 419.8 [M+H]+; 1H NMR (500 MHz, CDCl3) delta 10.48 (s, 1H), 8.18-8.10 (m, 3H), 8.03 (t, J=7.5 Hz, 1H), 7.95 (dd, J=7.5, 1.5 Hz, 1H), 7.67 (d, J=7.5 Hz, 1H), 7.38 (t, J=7.5 Hz, 1H), 4.39 (q, J=7.0 Hz, 2H), 3.68 (s, 3H), 1.40 (t, J=7.0 Hz, 3H).

Reference： [1]Patent: US2010/216764,2010,A1 .Location in patent: Page/Page column 23

5
[ 534-00-9 ]
[ 480424-49-5 ]
[ 1399799-09-7 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 9083 - 9090

6
[ 480424-49-5 ]
(R)-6-bromo-N-(1-phenylethyl)thieno[2,3-d]pyrimidin-4-amine hydrochloride [ No CAS ]
(R)-2-methoxy-3-(4-((1-phenylethyl)amino)thieno[2,3-d]pyrimidin-6-yl)benzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 80.0℃; for 5.0h;Inert atmosphere;	(R)-2-Methoxy-3-(4-((l-phenylethyl)amino)thieno[2,3-d]pyrimidin-6- yl)benzaldehyde ( (R)-l 7r) Compound ll -HCl (400 mg, 7.08 mmol), (3-formyl-2-metoksyphenyl)boronic acid (236 mg, 1.31 mmol), K3P04 (778 mg, 3.67 mmol) and Pd(PPh3)4 (13 mg, 11 piiotaomicron) were mixed with water (4 mL) and 1 ,4-dioksan (4 mL) under a nitrogen atmosphere. The mixture was stirred at 80 C for 5 h. The mixture evaporated to dryness, and mixed with diethyl ether (100 mL) and water (40 mL). After phase separation, the water phase was extracted with additional diethyl ether (2x60 mL). The combined organic fraction was dried over anhydrous Na2S04, concentrated and absorbed onto silica-gel. The product was purified by silica-gel column chromatography (CH2Cl2/EtOAc, 4/1), TLC (CH2Cl2/EtOAc, 4/1): Rf = 0.27, followed by crystallisation from diethyl ether using pentane as anti- solvent. After drying this gave 328 mg (0.842 mmol, 78%) of (i?)-17r as an slight yellowish solid; mp. 71 - 90 C; HPLC purity (Method A): 98%, tR = 28.0 min.; [a ]2 = -309.6 (c 0.60, DMSO). 1H NMR (400 MHz, DMSC /6) delta: 10.37 (s, 1H), 8.35 (s, 1H), 8.32 (d, J= 7.9, 1H), 8.32 (s, 1H), 8.09 - 8.07 (m, 1H), 7.83 - 7.81 (m, 1H), 7.50 - 7.46 (m, 1H), 7.45 - 7.43 (m, 2H), 7.35 - 7.31 (m, 2H), 7.24 - 7.21 (m, 1H), 5.58 - 5.51 (m, 1H), 3.85 (s, 3H), 1.58 (d, J= 7.0, 3H); 13C NMR (100 MHz, DMSC /6) delta: 189.8, 166.4, 159.0, 155.8, 154.2, 144.6, 131.7, 134.5, 129.9, 128.9, 128.3, 128.1 (2C), 126.7, 126.1 (2C), 125.3, 118.8, 116.2, 64.1, 49.0, 22.4; IR (neat, cm"1): 2967, 1688, 1577, 1508, 1351, 1305, 1245, 1105, 989, 777, 698. HRMS: (ASAP+, m/z): found 390.1272, (calcd. for C22H20N3O2S+, 390.1276, [M+H]+).
78%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 80.0℃;Inert atmosphere;	General procedure: Compounds II (200-1000 mg) were mixed with the selected boronic acid (1.2 eq), fine powdered K2CO3 (3 eq), Pd(PPh3)4 (0.01 eq) and 1,4-dioxane/water (1/1 by vol.%, 4-8 mL). The reaction was then stirred at 80 C for 2-5 h under nitrogen atmosphere.The solvent was removed and the product was diluted with water(25-50 mL) and extracted with Et2O or EtOAc (25-100 mL), the water phase was extracted with more diethyl ether or EtOAc (2 x 25 mL). The combined organic phases were washed with saturated aq NaCl solution (25 mL), dried over anhydrous Na2SO4,filtered and concentrated in vacuo. Purification was performed as specified for each individual compound. 4.7.28 (R)-2-Methoxy-3-(4-((1-phenylethyl)amino)thieno[2,3-d]pyrimidin-6-yl)benzaldehyde (26b) fx38 Compound 26b was prepared as described in Section 4.7 , starting with compound IIb·HCl (400 mg, 1.079 mmol) and (3-formyl-2-metoksyphenyl)boronic acid (233 mg, 1.295 mmol). The crude product was purified by silica-gel column chromatography (CH2Cl2/EtOAc, 4/1), Rf = 0.27, followed by crystallisation from Et2O/EtOAc (1/1) using n-pentane as anti-solvent. This gave 328 mg (0.842 mmol, 78%) of 26b as a slight yellowish solid; mp. 71-90 C; HPLC purity: 98%, tR = 28.0 min; [alpha]D20 = -309.6 (c 0.60, DMSO); 1H NMR (400 MHz, DMSO-d6) delta: 10.37 (s, 1H), 8.35 (s, 1H), 8.32 (d, J = 7.9, 1H), 8.32 (s, 1H), 8.09-8.07 (m, 1H), 7.83-7.81 (m, 1H), 7.50-7.46 (m, 1H), 7.45-7.43 (m, 2H), 7.35-7.31 (m, 2H), 7.24-7.21 (m, 1H), 5.58-5.51 (m, 1H), 3.85 (s, 3H), 1.58 (d, J = 7.0, 3H); 13C NMR (100 MHz, DMSO-d6) delta: 189.8, 166.4, 159.0, 155.8, 154.2, 144.6, 131.7, 134.5, 129.9, 128.9, 128.3, 128.1 (2C), 126.7, 126.1 (2C), 125.3, 118.8, 116.2, 64.1, 49.0, 22.4; IR (neat, cm-1): 2967, 1688, 1577, 1508, 1351, 1305, 1245, 1105, 989, 777, 698; HRMS (APCI/ASAP, m/z): found 390.1272, (calcd. for C22H20N3O2S, 390.1276, [M+H]+).

Reference： [1]Patent: WO2015/959,2015,A1 .Location in patent: Page/Page column 51-52
[2]European Journal of Medicinal Chemistry,2016,vol. 107,p. 255 - 274

7
[ 480424-49-5 ]
(R)-6-bromo-N-(1-phenylethyl)thieno[2,3-d]pyrimidin-4-amine hydrochloride [ No CAS ]
(R)-(2-methoxy-3-(4-((1-phenylethyl)amino)thieno[2,3-d]pyrimidin-6-yl)phenyl)methanol [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 107,p. 255 - 274

8
[ 480424-49-5 ]
[ 2923-66-2 ]
[ 19335-11-6 ]
(3-(9-(3-chloro-4-fluorophenyl)-3H-pyrazolo[4,3-f]quinolin-7-yl)-2-methoxyphenyl)boronic acid [ No CAS ]