[ CAS No. 473416-33-0 ] {[proInfo.proName]}

Name: 473416-33-0|(5-Fluorobenzofuran-2-yl)boronic acid|98%
Brand: Ambeed
SKU: A401687
Price: 39.0 USD
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Quality Control of [ 473416-33-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 473416-33-0 ]

SDS Specification

Alternatived Products of [ 473416-33-0 ]

Product Details of [ 473416-33-0 ]

CAS No. :	473416-33-0	MDL No. :	MFCD18383019
Formula :	C₈H₆BFO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YGLIPSIVUHENTJ-UHFFFAOYSA-N
M.W :	179.94	Pubchem ID :	22260896
Synonyms :

Calculated chemistry of [ 473416-33-0 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	46.0
TPSA :	53.6 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) :	-6.42 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.37
Log Po/w (WLOGP) :	0.67
Log Po/w (MLOGP) :	0.19
Log Po/w (SILICOS-IT) :	0.18
Consensus Log Po/w :	0.48

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.27
Solubility :	0.977 mg/ml ; 0.00543 mol/l
Class :	Soluble
Log S (Ali) :	-2.1
Solubility :	1.43 mg/ml ; 0.00797 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.46
Solubility :	0.63 mg/ml ; 0.0035 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.83

Safety of [ 473416-33-0 ]

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 [ 473416-33-0 ]

* 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 [ 473416-33-0 ]
Downstream synthetic route of [ 473416-33-0 ]

[ 473416-33-0 ] Synthesis Path-Upstream 1~5

1
[ 24410-59-1 ]
[ 5419-55-6 ]
[ 473416-33-0 ]

Yield	Reaction Conditions	Operation in experiment
26%	Stage #1: With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexane at -60 - -10℃; for 75 h; Inert atmosphere Stage #2: at -60 - 20℃; Inert atmosphere Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane	Step 3. 5-Fluorobenzofuran-2-ylboronic acid To a solution of 5-fluorobenzofuran (10 g, 73.53 mmol) in dry tetrahydrofuran (250 mL) was added tetramethylethylenediamine (10.2 g, 87.93 mmol). The solution was kept below -60° C. under nitrogen, while BuLi (93.75 mmol, 2.5M solution in hexane) was added dropwise. It was warmed to -10° C. during 45 min and stirred at this temperature for another 30 min. The mixture was cooled again below -60° C. followed by dropwise addition of triisopropyl borate (41.4 g, 220.21 mmol). After warming to room temperature the mixture was quenched with hydrochloric acid (70 mL, 2N) and stirred for 1 h. The alkaline aqueous layer was brought to pH 5 and extracted with ethyl acetate (3.x.80 mL). All organic layers were combined, dried over sodium sulfate, and concentrated in vacuo to give 5-fluorobenzofuran-2-ylboronic acid (3.5 g, 26percent) which was used for the next step without further purification.¹H-NMR (300 MHz, CDCl₃): δ 8.63 (s, 2H), 7.58-7.62 (m, 1H), 7.44-7.49 (m, 2H), 7.15-7.22 (m, 1H)

Reference： [1] Patent: US2012/225863, 2012, A1, . Location in patent: Page/Page column 17-18

2
[ 24410-59-1 ]
[ 150-46-9 ]
[ 473416-33-0 ]

Reference： [1] Patent: EP1380576, 2004, A1, . Location in patent: Page 67

3
[ 24410-59-1 ]
[ 5419-55-6 ]
[ 7732-18-5 ]
[ 473416-33-0 ]

Reference： [1] Patent: WO2012/119046, 2012, A2, . Location in patent: Page/Page column 66

4
[ 59769-37-8 ]
[ 473416-33-0 ]

Reference： [1] Patent: US2012/225863, 2012, A1,
[2] Patent: WO2012/119046, 2012, A2,

5
[ 371-41-5 ]
[ 473416-33-0 ]

Reference： [1] Patent: US2012/225863, 2012, A1,
[2] Patent: WO2012/119046, 2012, A2,

[ 473416-33-0 ] Synthesis Path-Downstream 1~27

1
[ 24410-59-1 ]
[ 150-46-9 ]
[ 473416-33-0 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20℃; for 3.33333h;	In a nitrogen atmosphere, to a solution of 2.0 g of <strong>[24410-59-1]5-fluorobenzofuran</strong> in 150 ml tetrahydrofuran was added 18.5 ml of a 1.59 M solution of n-butyllithium in n-hexane at-78C, and the mixture was stirred at the same temperature for 10 minutes and at 0C for further 10 minutes. At -78C, 3.7 ml of triethoxyborane was added, and the mixture was stirred for 2 hours while elevating to 0C. 30 ml of 1 N hydrochloric acid was added, stirred at room temperature for 1 hour, and then the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane = 1:3 to 1:1), to give 525 mg of the title compound as colorless crystals.1H-NMR (400 MHz, CDCl3) d 7.09 (1H, dt, J = 2.4, 8.8 Hz), 7.29 (1H, dd, J = 2.4, 8.8 Hz), 7.33 (1H, s), 7.44 (1H, dd, J = 4.0, 8.8 Hz).

Reference： [1]Patent: EP1380576,2004,A1 .Location in patent: Page 67

2
[ 473416-33-0 ]
[ 1384850-41-2 ]
[ 1384850-44-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 95℃; for 1h;Inert atmosphere;	5-Fluorobenzofuran-2-ylboronic acid (242.8 mg, 1.35 mmol), K3PO4 (284.8 mg, 1.35 mmol), Pd(PPh3)4 (25.9 mg, 0.02 mmol) and water (3 drops) were added to a solution of methyl 3- (l ,2,3,4-tetrahydroquinolin-l(2H)-yl)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate (Intermediare 1, 210 mg, 0.45 mmol,) in dioxane (5.0 rriL). The reaction was stirred for 1 h at 95C under an inert atmosphere of nitrogen in an oil bath. The reaction mixture was concentrated in vacuo and purified by a silica gel column chromatography with 2 % ethyl acetate in petroleum ether to afford methyl 3-(l ,2,3,4-tetrahydroquinolin-l(2H)-yl)-2-(5-fluorobenzofuran-2- yl)quinoxaline-6-carboxylate as a red solid (70 mg, 33 ).Calculated for C27H20FN3O3: 453.15. (ES, m/z): [M+H]+ 454.0'H-NMR (300 MHz, CDCI3): delta 8.65 (d, / = 1.5 Hz, 1H), 8.19 - 8.27 (m, 2H), 7.50 - 7.56 (m, 3H), 7.34 - 7.37 (m, 1H), 7.19 - 7.25 (m, 1H), 7.09 - 7.13 (m, 1H), 6.75 - 6.80 (m, 2H), 6.59 - 6.61 (m, 1H), 4.02 (s, 3H), 3.96 - 3.98 (t, / = 6.0 Hz, 2H), 3.00 - 3.04 (t, / = 6.6 Hz, 2H), 2.19 - 2.24 (t, J = 6.0 Hz, 2H)

Reference： [1]Patent: WO2012/94462,2012,A2 .Location in patent: Page/Page column 39

3
[ 473416-33-0 ]
[ 1384850-47-8 ]
[ 1384850-52-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 90℃; for 1h;Inert atmosphere;	To a solution of methyl 3-(6-methoxy-l ,2,3,4-tetrahydroquinolin-l-yl)-2- [(trifluoromethane)sulfonyloxy]quinoxaline-6-carboxylate (150 mg, crude) in dioxane (5.0 rriL) and water (three drops) was added (5-fluoro-l-benzofuran-2-yl)boronic acid (94 mg, 0.52 mmol), K3PO4 (165.8 g, 781.08 mmol) and Pd(PPh3)4 (15.3 mg, 13.08 mmol) with stirring for 1 h at 90C maintained with an inert atmosphere of nitrogen in an oil bath. The reaction mixture was concentrated under vacuum to give the residue, which was purified by a silica gel column with 2% ethyl acetate in petroleum to afford methyl 2-(5-fluoro-l-benzofuran-2-yl)-3-(6-methoxy- l ,2,3,4-tetrahydroquinolin-l-yl)quinoxaline-6-carboxylate as a red solid (40 mg).(ES, m/z): [M+H]+ 484.0'H-NMR (300 MHz, CDCI3) delta 8.61 (d, / = 1.8 Hz, 1H), 8.13 - 8.22 (m, 2H), 7.36 - 7.42 (m, 2H), 7.17 - 7.21 (m, 1H), 7.01 - 7.08 (m, 1H), 6.65 (d, / = 2.7 Hz, 1H), 6.56 (d, / = 8.7 Hz, 1H), 6.33 - 6.37 (m, 1H), 4.01 (s, 3H), 3.95 - 3.99 (t, / = 6.3 Hz, 2H), 3.63 (s, 3H), 2.93 - 2.98 (t, / = 6.6 Hz, 2H), 2.13 - 2.21 (m, 2H)

Reference： [1]Patent: WO2012/94462,2012,A2 .Location in patent: Page/Page column 49

4
[ 473416-33-0 ]
[ 1384850-50-3 ]
[ 1384850-55-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 90℃; for 1h;Inert atmosphere;	To a solution of methyl 3-(6-fluoro-3,4-dihydroquinolin-l (2H)-yl)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate (From Ex. 6, step 3, 200 mg, crude) in dioxane (5.0 mL) and three drops of water was added <strong>[473416-33-0]5-fluorobenzofuran-2-ylboronic acid</strong> (210 mg, 1.07 mmol), K3P04 (272 mg, 1.29 mmol) and Pd(PPh3)4 (25 mg, 0.02 mmol). The reaction was stirred for 1 h at 90C under an inert atmosphere of nitrogen in an oil bath. The reaction mixture was concentrated under vacuum to give the residue, which was purified by a silica gel column with 1 % to 5 % ethyl acetate in petroleum to afford methyl 2-(5-fluoro-lH-inden-2-yl)- 3-(6-fluoro-3,4-dihydroquinolin-l (2H)-yl)quinoxaline-6-carboxylate as a light red solid (59 mg)LC/MS (ES, m/z) [M+H]+ 472.0'H-NMR (300 MHz, CDC13) delta 8.65 (d, / = 1.5 Hz, 1H), 8.16 - 8.27 (m, 2H), 7.37 - 7.43 (m, 2H), 7.19 - 7.23 (m, 1H), 7.03 - 7.10 (m, 1H), 6.80 - 6.84 (m, 1H), 6.47 - 6.59 (m, 2H), 4.02 (s, 3H), 3.98 - 4.00 (m, 2H), 2.96 - 3.01 (t, / = 6.6 Hz, 2H), 2.15 - 2.24 (m, 2H)

Reference： [1]Patent: WO2012/94462,2012,A2 .Location in patent: Page/Page column 55

5
[ 473416-33-0 ]
[ 1268864-98-7 ]

Reference： [1]Patent: US2012/225863,2012,A1
[2]Patent: WO2012/119046,2012,A2

6
[ 59769-37-8 ]
[ 473416-33-0 ]

Reference： [1]Patent: US2012/225863,2012,A1
[2]Patent: WO2012/119046,2012,A2

7
[ 371-41-5 ]
[ 473416-33-0 ]

Reference： [1]Patent: US2012/225863,2012,A1
[2]Patent: WO2012/119046,2012,A2

8
[ 473416-33-0 ]
[ 1394972-91-8 ]
[ 1396752-49-0 ]