[ CAS No. 65148-10-9 ] {[proInfo.proName]}

Name: 65148-10-9|6-Bromoquinoline-2-carboxylic acid|97%
Brand: Ambeed
SKU: A262481
Price: 59.0 USD
Availability: InStock
Rating: 90 (30 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 65148-10-9 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 65148-10-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 65148-10-9 ]

SDS Specification

Alternatived Products of [ 65148-10-9 ]

Product Details of [ 65148-10-9 ]

CAS No. :	65148-10-9	MDL No. :	MFCD09834121
Formula :	C₁₀H₆BrNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UQGCFISFRKCLOL-UHFFFAOYSA-N
M.W :	252.06	Pubchem ID :	12386208
Synonyms :

Calculated chemistry of [ 65148-10-9 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	56.4
TPSA :	50.19 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.89 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.57
Log Po/w (XLOGP3) :	2.74
Log Po/w (WLOGP) :	2.7
Log Po/w (MLOGP) :	0.93
Log Po/w (SILICOS-IT) :	2.47
Consensus Log Po/w :	2.08

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-3.59
Solubility :	0.0646 mg/ml ; 0.000256 mol/l
Class :	Soluble
Log S (Ali) :	-3.45
Solubility :	0.0897 mg/ml ; 0.000356 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.93
Solubility :	0.0295 mg/ml ; 0.000117 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.36

Safety of [ 65148-10-9 ]

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 [ 65148-10-9 ]

* 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 [ 65148-10-9 ]
Downstream synthetic route of [ 65148-10-9 ]

[ 65148-10-9 ] Synthesis Path-Upstream 1~8

1
[ 1020567-35-4 ]
[ 65148-10-9 ]

Yield	Reaction Conditions	Operation in experiment
96%	at 150℃; for 5.25 h;	1b) 6-Bromo-2-quinolinecarboxylic Acid Concentrated sulfuric acid (0.75 L) was added during 15 min to a stirred suspension of 6-bromo-2-(tribromomethyl)quinoline (350 g, 0.76 mol) in water (1.75 L). The resulting suspension was heated at 150° C. (bath temperature) for 5 hr. The mixture was cooled and the precipitate was collected by filtration, washed with water and dried to give 6-bromo-2-quinolinecarboxylic acid as a solid (127.6 g). The filtrate was diluted with water (3 L) and a second crop of the product was obtained (55.7 g, combined yield 183.3 g, 96percent). ¹H NMR (400 MHz, DMSO-d₆): δ 8.50 (d, J=9 Hz, 1H), 8.38 (d, J=2 Hz, 1H), 8.13 (d, J=9 Hz, 1H), 8.06 (d, J=9 Hz, 1H), 7.96 (m, 1H). ES-LCMS m/z 253 (M+H)⁺.

Reference： [1] Patent: US2008/96921, 2008, A1, . Location in patent: Page/Page column 32
[2] Journal of Labelled Compounds and Radiopharmaceuticals, 1998, vol. 41, # 12, p. 1103 - 1126

2
[ 877-42-9 ]
[ 65148-10-9 ]

Reference： [1] Journal of Labelled Compounds and Radiopharmaceuticals, 1998, vol. 41, # 12, p. 1103 - 1126
[2] Patent: WO2011/127643, 2011, A1, . Location in patent: Page/Page column 37
[3] Tetrahedron, 2014, vol. 70, # 42, p. 7686 - 7690

3
[ 65185-41-3 ]
[ 65148-10-9 ]

Yield	Reaction Conditions	Operation in experiment
46%	for 19 h; Reflux	General Procedure VII-ABCompound VII-VIIIc (1 g, 0.3 mmol) was dissolved in concentrated hydrochloric acid aqueous (40 mL). The solution was stirred and heated to reflux for 19 h. After the mixture was cooled to room temperature, the precipitate was collected by filtration, and was washing with water, to give compound VII-VIIId (0.6 g, yield: 46percent). MS (ESI) m/z (M+H)⁺253.9.

Reference： [1] Patent: US2011/152246, 2011, A1, . Location in patent: Page/Page column 270
[2] Patent: WO2014/146491, 2014, A1, . Location in patent: Page/Page column 120

4
[ 623583-88-0 ]
[ 65148-10-9 ]

Reference： [1] Patent: US2005/165049, 2005, A1, . Location in patent: Page/Page column 22

5
[ 5332-25-2 ]
[ 65148-10-9 ]

Reference： [1] Patent: US2011/152246, 2011, A1,

6
[ 6563-11-7 ]
[ 65148-10-9 ]

Reference： [1] Patent: US2011/152246, 2011, A1,

7
[ 106-40-1 ]
[ 65148-10-9 ]

Reference： [1] Tetrahedron, 2014, vol. 70, # 42, p. 7686 - 7690

8
[ 67-56-1 ]
[ 65148-10-9 ]
[ 623583-88-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: for 6 h; Heating / reflux Stage #2: With water; sodium hydrogencarbonate In methanol at 20℃;	1c) Methyl 6-bromo-2-quinolinecarboxylate A mixture of 6-bromo-2-quinolinecarboxylic acid (331 g, from multiple batches, 1.31 mol) and methanesulfonic acid (22 mL, 33 g, 0.34 mol) in methanol (2 L) was refluxed for 6 hr. The mixture was treated with a solution of sodium bicarbonate (29 g, 0.34 mol) in water (350 mL) and the resulting suspension was slowly cooled to 20° C. and stirred overnight. The suspension was filtered and the cake was washed with water (1 L). The solid was dried in a vacuum oven at 50° C. for 3 days to yield methyl 6-bromo-2-quinolinecarboxylate (294 g, 85percent). ¹H NMR (400 MHz, DMSO-d₆) δ 8.52 (d, J=9 Hz, 1H), 8.40 (d, J=2 Hz, 1H), 8.14 (d, J=9 Hz, 1H), 8.08 (d, J=9 Hz, 1H), 7.97 (m, 1H), 3.93 (s, 3H). ES-LCMS m/z 267 (M+H)⁺.
83%	for 3 h; Reflux	General procedure: Quinoline-2-carboxylic acid (10.0 mmol) was dissolved in dry MeOH and placed in an ice bath. SOCl₂ (0.92 mL, 12.0 mmol) was then added dropwise and the mixture was refluxed overnight until the starting material was undetectable by TLC. The suspension was cooled to room temperature and carefully poured into an aqueous, saturated NaHCO₃ solution. The resulting mixture was extracted twice with CH₂Cl₂. The organic extracts were combined, dried over anhydrous Na₂SO₄, and filtered, and the solvent was then removed by evaporation in vacuum. The resulting residue was purified by column chromatography to obtain the pure ester. 4.3.4 Methyl quinoline-2-carboxylate analog 1d (yield: 83percent) Colorless Solid. ¹H NMR (500 MHz, CDCl₃) δ 8.21 (s, 2H), 8.17 (d, J=9.0 Hz, 1H), 8.05 (d, J=2.1 Hz, 1H), 7.85 (dd, J=9.0, 2.2 Hz, 1H), 4.09 (s, 3H). ¹³C NMR (125 MHz, CDCl₃) δ 165.6, 148.2, 146.1, 136.3, 133.9, 132.3, 130.3, 129.6, 123.0, 121.9, 53.3. ESI-HRMS m/z [M+H]⁺ calcd for C₁₁H₉BrNO₂ 265.9817, found 265.9821.

Reference： [1] Patent: US2008/96921, 2008, A1, . Location in patent: Page/Page column 32
[2] Tetrahedron, 2014, vol. 70, # 42, p. 7686 - 7690
[3] Patent: WO2011/127643, 2011, A1, . Location in patent: Page/Page column 38

[ 65148-10-9 ] Synthesis Path-Downstream 1~61

1
[ 6066-82-6 ]
[ 65148-10-9 ]
6-bromoquinaldic acid-hydroxysuccinimide ester [ No CAS ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,1998,vol. 41,p. 1103 - 1126

2
[ 1020567-35-4 ]
[ 65148-10-9 ]

Yield	Reaction Conditions	Operation in experiment
96%	With sulfuric acid; water; at 150℃; for 5.25h;	1b) 6-Bromo-2-quinolinecarboxylic Acid Concentrated sulfuric acid (0.75 L) was added during 15 min to a stirred suspension of 6-bromo-2-(tribromomethyl)quinoline (350 g, 0.76 mol) in water (1.75 L). The resulting suspension was heated at 150 C. (bath temperature) for 5 hr. The mixture was cooled and the precipitate was collected by filtration, washed with water and dried to give 6-bromo-2-quinolinecarboxylic acid as a solid (127.6 g). The filtrate was diluted with water (3 L) and a second crop of the product was obtained (55.7 g, combined yield 183.3 g, 96%). 1H NMR (400 MHz, DMSO-d6): delta 8.50 (d, J=9 Hz, 1H), 8.38 (d, J=2 Hz, 1H), 8.13 (d, J=9 Hz, 1H), 8.06 (d, J=9 Hz, 1H), 7.96 (m, 1H). ES-LCMS m/z 253 (M+H)+.

Reference： [1]Patent: US2008/96921,2008,A1 .Location in patent: Page/Page column 32
[2]Journal of labelled compounds and radiopharmaceuticals,1998,vol. 41,p. 1103 - 1126

4
[ 67-56-1 ]
[ 65148-10-9 ]
[ 623583-88-0 ]

Yield	Reaction Conditions	Operation in experiment
85%		1c) Methyl 6-bromo-2-quinolinecarboxylate A mixture of <strong>[65148-10-9]6-bromo-2-quinolinecarboxylic acid</strong> (331 g, from multiple batches, 1.31 mol) and methanesulfonic acid (22 mL, 33 g, 0.34 mol) in methanol (2 L) was refluxed for 6 hr. The mixture was treated with a solution of sodium bicarbonate (29 g, 0.34 mol) in water (350 mL) and the resulting suspension was slowly cooled to 20 C. and stirred overnight. The suspension was filtered and the cake was washed with water (1 L). The solid was dried in a vacuum oven at 50 C. for 3 days to yield methyl 6-bromo-2-quinolinecarboxylate (294 g, 85%). 1H NMR (400 MHz, DMSO-d6) delta 8.52 (d, J=9 Hz, 1H), 8.40 (d, J=2 Hz, 1H), 8.14 (d, J=9 Hz, 1H), 8.08 (d, J=9 Hz, 1H), 7.97 (m, 1H), 3.93 (s, 3H). ES-LCMS m/z 267 (M+H)+.
83%	With thionyl chloride; for 3h;Reflux;	General procedure: Quinoline-2-carboxylic acid (10.0 mmol) was dissolved in dry MeOH and placed in an ice bath. SOCl2 (0.92 mL, 12.0 mmol) was then added dropwise and the mixture was refluxed overnight until the starting material was undetectable by TLC. The suspension was cooled to room temperature and carefully poured into an aqueous, saturated NaHCO3 solution. The resulting mixture was extracted twice with CH2Cl2. The organic extracts were combined, dried over anhydrous Na2SO4, and filtered, and the solvent was then removed by evaporation in vacuum. The resulting residue was purified by column chromatography to obtain the pure ester. 4.3.4 Methyl quinoline-2-carboxylate analog 1d (yield: 83%) Colorless Solid. 1H NMR (500 MHz, CDCl3) delta 8.21 (s, 2H), 8.17 (d, J=9.0 Hz, 1H), 8.05 (d, J=2.1 Hz, 1H), 7.85 (dd, J=9.0, 2.2 Hz, 1H), 4.09 (s, 3H). 13C NMR (125 MHz, CDCl3) delta 165.6, 148.2, 146.1, 136.3, 133.9, 132.3, 130.3, 129.6, 123.0, 121.9, 53.3. ESI-HRMS m/z [M+H]+ calcd for C11H9BrNO2 265.9817, found 265.9821.
	With hydrogenchloride; for 5h;Reflux;	Step B: Methyl 6-bromoquinoline-2-carboxylateTo a solution of <strong>[65148-10-9]6-bromoquinoline-2-carboxylic acid</strong> (98 mg, 0.39 mmol) in MeOH (5 mL), hydrochloride gas was bubbled through for 5 min, and the mixture was heated at reflux for 5 h. Concentration of the resulting mixture afforded the title compound, which was used without further purification. LCMS: m/e 266 [M+H]+.

Reference： [1]Patent: US2008/96921,2008,A1 .Location in patent: Page/Page column 32
[2]Tetrahedron,2014,vol. 70,p. 7686 - 7690
[3]Patent: WO2011/127643,2011,A1 .Location in patent: Page/Page column 38

5
[ 6638-79-5 ]
[ 65148-10-9 ]
6-bromo-N-methoxy-N-methylquinoline-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 3h;	A solution of <strong>[65148-10-9]6-bromoquinoline-2-carboxylic acid</strong> (308 mg, 1.222 mmol), N,O-dimethylhydroxylamine hydrochloride (143 mg, 1.466 mmol), 2-(lH- benzo [d] [ 1 ,2,3 jtriazol- 1 -yl)- 1 , 1 ,3 ,3 -tetramethyluronium hexafluorophosphate(V) (602 mg, 1.588 mmol) and DIEA (512 mu, 2.93 mmol) in DMF (Volume: 2.44 mL) was stirred at room temperature for 3 h. The reaction mixture was quenched with saturated aqueous sodium bicarbonate and extracted with ethyl acetate (3x10 mL). The combined organics and washed with brine (1x10 mL), dried (MgS04), filtered and concentrated under reduced pressure. The residue was purified via silica gel chromatography (15%-20% EtOAc in hexanes) to afford 6-bromo-N-methoxy-N- methylquinoline-2-carboxamide (347 mg, 1.15 mmol, 94 % yield) as a pale yellow oil: 1H NMR (400MHz, CHLOROFORM-d) 5 8.18 (d, J=8.5 Hz, 1H), 8.05 (d, J=2.3 Hz, 1H), 8.02 (d, J=9.0 Hz, 1H), 7.84 (dd, J=9.0, 2.3 Hz, 1H), 7.72 (br. s., 1H), 3.79 (br. s., 3H), 3.47 (br. s., 3H); LCMS (ESI) mle 295.0, 297.0 Br pattern [(M+H)+, calcd for Ci2Hi2BrN202 295.0].
92%	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 24h;	To a DMF (1 ml) solution of <strong>[65148-10-9]6-bromoquinoline-2-carboxylic acid</strong> (4000 mg, 15.9 mmol, US2005165049A1), triethylamine (6.64 ml, 47.6 mmol), N1O -dimethylhydroxyamine hydrochloride (1860 mg, 19.0 mmol) and HBTU (6620 mg, 17.5 mmol) were added and the mixture was stirred for 24 hours at room temperature. The reaction was quenched with saturated NaHCO3 aqueous solution and water, and the product was extracted with EtOAc 3 times. The combined organic extracts were dried over Na2SO4, and concentrated in vacuo. The crude residue was applied to a silica gel column chromatography and eluted with hexane/ethyl acetate (4:1 ) to furnish the title compound (4.29 g, 92% yield) as an orange solid. 1H NMR (300MHz, CDCI3) delta 3.47 (3H, s), 3.80 (3H, s), 7.68-7.80 (1 H, brs), 7.81 -7.85 (1 H, m), 8.00-8.06 (2H, m), 8.17 (1H, d, J = 8.1 Hz). MS (ESI) : m/z 295, 297 (M + H)+.
44%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine;dmap; In dichloromethane; at 0 - 20℃;	Intermediate 14; At 0C, to a stirred suspension of <strong>[65148-10-9]6-bromo-2-carboxyquinoline</strong> (1.45g,5.57mmol), EDCI (1.32g, 6.9mmol), DMAP (cat.) and Nu,Omicron-dimethylhydroxylamine HCl (0.62g, 6.33 mmol) in DCM was added TEA (1.7g, 17 mmol). After addition, the reaction mixture became clear. Stirring was continued overnight at rt. before quenched with NaHC03 (ss). The layers were separated and the organic layer was washed with brine, dried over Na2S04. After evaporation of the solvents, the crude product was purified by column chromatography (silica gel, 0 to 30% EtOAc in hexanes) to give 6- bromo-N-methoxy-N-methylquinoline-2-carboxamide (intermediate 14) (750mg, 44%) as an oil which was slowly solidified. NMR (400MHz, CHLOROFORM-d) . 8.16 (d, J= 8.4 Hz, 1 H), 8.08 - 7.93 (m, 2 H), 7.81 (dd, J= 2.1, 9.0 Hz, 1 H), 7.74 - 7.56 (m, 1 H), 3.77 (br. s? 3 H), 3.45 (br. s., 3 H). ES LC-MS m/z = 296.7 (M+H)+

Reference： [1]Patent: WO2015/116492,2015,A1 .Location in patent: Page/Page column 62-63
[2]Patent: WO2008/59370,2008,A2 .Location in patent: Page/Page column 55
[3]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 6079 - 6085
[4]Inorganic Chemistry,2016,vol. 55,p. 11908 - 11919
[5]Patent: WO2011/91446,2011,A1 .Location in patent: Page/Page column 9; 20

6
[ 877-42-9 ]
[ 65148-10-9 ]

Yield	Reaction Conditions	Operation in experiment
	With selenium(IV) oxide; In pyridine; at 100℃;	INTERMEDIATE EXAMPLE 8Step A: 6-Bromoquinoline-2-carbox lic acidTo a solution of 6-bromo-2-methylquinoline (100 mg, 0.45 mmol) in pyridine (5 mL), selenium dioxide (110 mg, 1.0 mmol) was added. After heating at 100C overnight, the resulting mixture was filtered, and the filtrate was concentrated. The residue was purified on a silica gel column eluting with PE:EtOAc (3 : 1 to 2: 1) to afford the title compound. LCMS: m/e 252

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,1998,vol. 41,p. 1103 - 1126
[2]Patent: WO2011/127643,2011,A1 .Location in patent: Page/Page column 37
[3]Tetrahedron,2014,vol. 70,p. 7686 - 7690

7
[ 65148-10-9 ]
[ 219959-35-0 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,1998,vol. 41,p. 1103 - 1126

8
[ 65148-10-9 ]
N-tert.butyl-decahydro-2-[2-(R)-hydroxy-4-phenyl-3(S)-[{N-(2-[6-tritio]-quinolylcarbonyl)-L-asparaginyl}amino]butyl]-(4aS,8aS)-isoquinoline-3-carboxamide [ No CAS ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,1998,vol. 41,p. 1103 - 1126

9
[ 106-40-1 ]
p-CH₃C₆H₄)2As(O)-ester [ No CAS ]
[ 65148-10-9 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,1998,vol. 41,p. 1103 - 1126

10
[ 623583-88-0 ]
[ 65148-10-9 ]

Yield	Reaction Conditions	Operation in experiment
		(b) 6-Bromo-quinoline-2-carboxylic acid. A mixture of 6-bromo-quinoline-2-carboxylic acid methyl ester, Example 36(a), (168 mg, 0.63 mmol), LiOH (30 mg, 1.26 mmol), MeOH (2 mL) and water (2 mL) was heated at 80 C. for 30 min. The reaction mixture was cooled to room temperature, acidified with 1 N HCl and extracted with EtOAc (2*15 mL). The EtOAc extracts were combined, washed with brine, dried over MgSO4, and filtered. The filtrate was evaporated in vacuo to give the title compound as a brown solid. MS (ESI, pos. ion) m/z: 253 (M+1).

Reference： [1]Patent: US2005/165049,2005,A1 .Location in patent: Page/Page column 22

11
[ 65148-10-9 ]
[ 124-40-3 ]
[ 1199806-00-2 ]

Yield	Reaction Conditions	Operation in experiment
90%		Suspended the <strong>[65148-10-9]6-bromoquinoline-2-carboxylic acid</strong> (1.0 g, 3.93 mmol) in CH2Cl2 (20 ml), added DMF (0.912 ml, 11.78 mmol) and cooled in an ice bath. Added oxalyl chloride (0.688 ml, 7.86 mmol) dropwise over a few min. Warmed to rt and stirred for 1 hr then bubbled in dimethylamine gas for several min. Stirred the dark amber mixture at rt overnight. Diluted with water and extracted with CH2Cl2 (3x). Washed extracts with brine (Ix), dried over MgSO^ decolorized with charcoal, filtered, evaporated and dried under high vac, rt. Amber oil which solidified on drying, wt - 990 mg (90%). LC-MS : [M+H]+ = 279, 281.
		INTERMEDIATE 916-Bromo- N . N -dimethylquinoline-2-carboxamideSuspended the <strong>[65148-10-9]6-bromoquinoline-2-carboxylic acid</strong> (1.0 g, 3.93 mmol) in CH2Cl2 (20 mL), added DMF (0.91 mL, 11.78 mmol) and cooled in an ice bath. Added oxalyl chloride (0.688 mL, 7.86 mmol) dropwise over a few min. Warmed to rt and stirred for 1 hr then bubbled in dimethylamine gas for several min. The dark amber mixture was stirred at rt overnight, hi am, the solution was diluted with water and extracted with CH2Cl2 (3x). Washed extracts with brine (Ix), dried over MgSO,*, decolorized with charcoal, filtered, evaporated and dried under high vac, rt to afford the title compound (990mg). LC/MS: m/e 279, 281(M+H)+.
		Suspended the <strong>[65148-10-9]6-bromoquinoline-2-carboxylic acid</strong> (1.0 g, 3.93 mmol) in CH2Cl2 (20 mL), added DMF (0.91 mL, 11.78 mmol) and cooled in an ice bath. Added oxalyl chloride (0.688 mL, 7.86 mmol) dropwise over a few min. Warmed to rt and stirred for 1 hr then bubbled in dimethylamine gas for several min. The dark amber mixture was stirred at rt overnight. In am, the solution was diluted with water and extracted with CH2Cl2 (3×). Washed extracts with brine (1×), dried over MgSO4, decolorized with charcoal, filtered, evaporated and dried under high vac, rt to afford the title compound (990 mg). LC/MS: m/e 279, 281 (M+H)+.

6-Bromoquinoline-2-carboxylic acid (40 mg, 0.16 mmol) and HATU (121 mg, 0.317 mmol) were dissolved in DMF (0.50 mL) and stirred at room temperature for 5 minutes. A separate solution of DMF (0.50 mL), dimethylamine (0.159 mL, 0.317 mmol, 2M in THF)) and DIPEA (0.083 mL, 0.48 mmol) was then added and the reaction was stirred at room temperature for 1 hour before being diluted with EtOAc, and washed with water. The organic layer was then dried using MgSC"4, filtered, and concentrated in vacuo to give the title compound. 1H NMR (500 MHz, CDC13): delta 8.17 (d, / = 8.2 Hz, 1H), 8.02 (s, 1H), 7.98 (d, / = 8.2 Hz, 1H), 7.82 (d, / = 8.2 Hz, 1H), 7.74 (d, / = 8.2 Hz, 1H), 3.20 (s, 3H), 3.16 (s, 3H)

Reference： [1]Patent: WO2009/152025,2009,A1 .Location in patent: Page/Page column 87
[2]Patent: WO2010/17079,2010,A1 .Location in patent: Page/Page column 89
[3]Patent: US2011/21531,2011,A1 .Location in patent: Page/Page column 42; 43
[4]Patent: WO2014/146491,2014,A1 .Location in patent: Page/Page column 120

12
[ 65148-10-9 ]
[ 75-65-0 ]
[ 1312611-18-9 ]