[ CAS No. 1001756-23-5 ] {[proInfo.proName]}

Name: 1001756-23-5|Methyl 7-bromoquinoline-3-carboxylate|98%
Brand: Ambeed
SKU: A142510
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Quality Control of [ 1001756-23-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1001756-23-5 ]

SDS Specification

Alternatived Products of [ 1001756-23-5 ]

Product Details of [ 1001756-23-5 ]

CAS No. :	1001756-23-5	MDL No. :	MFCD09834664
Formula :	C₁₁H₈BrNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GPLUSJRHUJLUHU-UHFFFAOYSA-N
M.W :	266.09	Pubchem ID :	59321547
Synonyms :

Calculated chemistry of [ 1001756-23-5 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.09
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	60.72
TPSA :	39.19 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.84 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.51
Log Po/w (XLOGP3) :	2.94
Log Po/w (WLOGP) :	2.78
Log Po/w (MLOGP) :	2.32
Log Po/w (SILICOS-IT) :	2.96
Consensus Log Po/w :	2.7

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.7
Solubility :	0.0527 mg/ml ; 0.000198 mol/l
Class :	Soluble
Log S (Ali) :	-3.43
Solubility :	0.1 mg/ml ; 0.000376 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.63
Solubility :	0.00622 mg/ml ; 0.0000234 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.59

Safety of [ 1001756-23-5 ]

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 [ 1001756-23-5 ]

* 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.

Upstream synthesis route of [ 1001756-23-5 ]
Downstream synthetic route of [ 1001756-23-5 ]

[ 1001756-23-5 ] Synthesis Path-Upstream 1~4

1
[ 1020567-86-5 ]
[ 1001756-23-5 ]

Yield	Reaction Conditions	Operation in experiment
16%	Stage #1: With [bis(acetoxy)iodo]benzene; iodine In 1,2-dichloro-ethane at 70℃; for 0.5 h; Stage #2: With potassium carbonate In 1,2-dichloro-ethane; N,N-dimethyl-formamide at 120℃; for 6 h;	2c) Methyl 7-bromo-3-quinolinecarboxylate A solution of 820 mg (1.93 mmol) of methyl (2E)-3-(4-bromophenyl)-2-([(4-methylphenyl)sulfonyl]amino}methyl)-2-propenoate, 995 mg (3.09 mmol) of bis(acetyloxy)(phenyl)-λ³-iodane and 490 mg (1.93 mmol) of iodine in 35 mL of 1,2-dichloroethane were stirred at 70° C. for 30 min. The solvent was evaporated and the residue taken up in 25 mL DMF and 1.07 g (7.73 mmol) of K₂CO₃ was added. The mixture was stirred at 120° C. for 6 hr. EtOAc was added and the organics were washed with three portions of H₂O then brine. The solution was then concentrated and the residue purified by silica gel chromatography (40 g of silica gel eluding with 0-40percent EtOAc in hexanes over 45 minutes) to give 80 mg (16percent) of methyl 7-bromo-3-quinolinecarboxylate as an off-white solid. ¹H NMR (400 MHz, CDCl₃): δ 9.34 (s, 1H), 8.81 (s, 1H), 8.35 (s, 1H), 7.80 (d, J=9 Hz, 1H), 7.73 (d, J=9 Hz, 1H), 4.02 (s, 3H). ESI-LCMS m/z 267 (M+H)⁺.

Reference： [1] Patent: US2008/96921, 2008, A1, . Location in patent: Page/Page column 35

2
[ 1416560-86-5 ]
[ 1001756-23-5 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 1, p. 188 - 193

3
[ 3132-99-8 ]
[ 1001756-23-5 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 1, p. 188 - 193

4
[ 500163-43-9 ]
[ 1001756-23-5 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 1, p. 188 - 193

[ 1001756-23-5 ] Synthesis Path-Downstream 1~14

1
[ 1020567-86-5 ]
[ 1001756-23-5 ]

Yield	Reaction Conditions	Operation in experiment
16%		2c) Methyl 7-bromo-3-quinolinecarboxylate A solution of 820 mg (1.93 mmol) of methyl (2E)-3-(4-bromophenyl)-2-([(4-methylphenyl)sulfonyl]amino}methyl)-2-propenoate, 995 mg (3.09 mmol) of bis(acetyloxy)(phenyl)-lambda3-iodane and 490 mg (1.93 mmol) of iodine in 35 mL of 1,2-dichloroethane were stirred at 70° C. for 30 min. The solvent was evaporated and the residue taken up in 25 mL DMF and 1.07 g (7.73 mmol) of K2CO3 was added. The mixture was stirred at 120° C. for 6 hr. EtOAc was added and the organics were washed with three portions of H2O then brine. The solution was then concentrated and the residue purified by silica gel chromatography (40 g of silica gel eluding with 0-40percent EtOAc in hexanes over 45 minutes) to give 80 mg (16percent) of methyl 7-bromo-3-quinolinecarboxylate as an off-white solid. 1H NMR (400 MHz, CDCl3): delta 9.34 (s, 1H), 8.81 (s, 1H), 8.35 (s, 1H), 7.80 (d, J=9 Hz, 1H), 7.73 (d, J=9 Hz, 1H), 4.02 (s, 3H). ESI-LCMS m/z 267 (M+H)+.

Reference： [1]Patent: US2008/96921,2008,A1 .Location in patent: Page/Page column 35

2
[ 1001756-23-5 ]
[ 269409-70-3 ]
[ 1276656-22-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate;palladium diacetate; triphenylphosphine; In 1,4-dioxane; water; at 60℃; for 1h;	2d) Methyl 7-[4-([3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-quinolinecarboxylate A solution of 78 mg (0.29 mmol) of <strong>[1001756-23-5]methyl 7-bromo-3-quinolinecarboxylate</strong>, 97 mg (0.44 mmol) of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, 3 mg (0.01 mmol) of palladium acetate, 8 mg (0.03 mmol) of triphenylphosphine, 218 mg (1.03 mmol) of K3PO4 and 25 muL of H2O in 1.0 mL of dioxane was stirred at 60° C. for 1 hr. EtOAc was added and the organics were washed with water and brine then concentrated. To the residue was added 65 mg (0.21 mmol) of 4-(chloromethyl)-3-(2,6-dichlorophenyl)-5-(1-methylethyl)isoxazole, 74 mg (0.54 mmol) of K2CO3 and 1.5 mL of DMF and the mixture was then stirred at 60° C. for 1 hr. EtOAc was added and the organics were washed with three portions of water, then brine. The solution was concentrated and the residue purified by silica gel chromatography (12 g of silica gel eluding with 0-40percent EtOAc in hexanes over 45 minutes) to give 47 mg (30percent) of methyl 7-[4-([3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-quinolinecarboxylate as a clear glass. 1H NMR (400 MHz, CDCl3): delta 9.44 (s, 1H), 8.83 (s, 1H), 8.28 (s, 1H), 7.96 (d, J=9 Hz, 1H), 7.82 (d, J=9 Hz, 1H), 7.64 (d, J=9 Hz, 2H), 7.41 (d, J=8 Hz, 2H), 7.35-7.31 (m, 1H), 6.92 (d, J=9 Hz, 2H), 4.79 (s, 2H), 4.02 (s, 3H), 3.38-3.34 (m, 1H), 1.45 (d, J=7 Hz, 6H). ESI-LCMS m/z 548 (M+H)+.
	With potassium phosphate; palladium diacetate; triphenylphosphine; In 1,4-dioxane; water; at 60℃; for 1h;	A solution of <strong>[1001756-23-5]methyl 7-bromo-3-quinolinecarboxylate</strong> 2c (78 mg, 0.29 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol 3b (97 mg, 0.44 mmol), palladium(II) acetate (3 mg, 0.01 mmol), triphenylphosphine (8 mg, 0.03 mmol), potassium phosphate (218 mg, 1.03 mmol), and water (25 muL) in dioxane (1.0 mL) was stirred at 60 °C for 1 hour. Ethyl acetate was added and the organics were washed with water and brine, and then concentrated to give methyl 7-(4-hydroxyphenyl)quinoline-3-carboxylate 4c. To methyl 7-(4-hydroxyphenyl)quinoline-3-carboxylate 4c was added 4-(chloromethyl)-3-(2,6-dichlorophenyl)-5-(1-methylethyl)isoxazole 5a (65 mg, 0.21 mmol), potassium carbonate (74 mg, 0.54 mmol) and N,N-dimethylformamide (1.5 mL) and the mixture was then stirred at 60 °C for 1 hour. Ethyl acetate was added and the organics were washed with three portions of water, then brine. The solution was concentrated, and the residue was purified by silica gel chromatography (hexanes to 2:3 ethyl acetate:hexanes) to give methyl 7-[4-([3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-quinolinecarboxylate (47 mg, 30percent) as a clear glass (1H NMR (400 MHz, CDCl3): 9.44 (s, 1H), 8.83 (s, 1H), 8.28 (s, 1H), 7.96 (d, J = 9 Hz, 1H), 7.82 (d, J = 9 Hz, 1H), 7.64 (d, J = 9 Hz, 2H), 7.41 (d, J = 8 Hz, 2H), 7.35-7.31 (m, 1H), 6.92 (d, J = 9 Hz, 2H), 4.79 (s, 2H), 4.02 (s, 3H), 3.38-3.34 (m, 1H), 1.45 (d, J = 7 Hz, 6H); ESI-LCMS m/z 548 (M+H)). To methyl 7-[4-([3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-quinolinecarboxylate (47 mg, 0.09 mmol) in a mixture of ethanol (3 mL), tetrahydrofuran (1 mL), and water (1 mL) was added sodium hydroxide (35 mg, 0.86 mmol) and the mixture stirred at 50 °C for 16 hours. The mixture was concentrated to 1/3 volume then added dropwise to a stirred solution of 0.5 N hydrochloric acid (10 mL). The resulting solids were collected by suction filtration, washed with water, then dried to yield 7-[4-([3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-quinolinecarboxylic acid 1e (32 mg, 70percent) as a yellow solid. 1H NMR (400 MHz, DMSO-d6): delta 9.30 (s, 1H), 8.97 (s, 1H), 8.24-8.21 (m, 2H), 7.99 (d, J = 8 Hz, 1H), 7.76 (d, J = 8 Hz, 2H), 7.63-7.61 (m, 2H), 7.55-7.52 (m, 1H), 6.93 (d, J = 9 Hz, 2H), 4.88 (s, 2H), 3.50-3.44 (septet, J = 7 Hz, 1H), 1.33 (d, J = 7 Hz, 6H); ESI-LCMS m/z 534 (M+H).

Reference： [1]Patent: US2008/96921,2008,A1 .Location in patent: Page/Page column 35-36
[2]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1206 - 1213

3
[ 1001756-23-5 ]
[ 1020567-95-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1206 - 1213

4
[ 1001756-23-5 ]
[ 1020567-77-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1206 - 1213

5
[ 3132-99-8 ]
[ 1001756-23-5 ]