[ CAS No. 928839-62-7 ] {[proInfo.proName]}

Name: 928839-62-7|5-Bromoquinoline-8-carboxylic acid|98%
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SKU: A117397
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Quality Control of [ 928839-62-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 928839-62-7 ]

SDS Specification

Alternatived Products of [ 928839-62-7 ]

Product Details of [ 928839-62-7 ]

CAS No. :	928839-62-7	MDL No. :	MFCD19689072
Formula :	C₁₀H₆BrNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SMDUUZMMJKRMDS-UHFFFAOYSA-N
M.W :	252.06	Pubchem ID :	59292860
Synonyms :

Calculated chemistry of [ 928839-62-7 ]

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) :	-6.17 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.53
Log Po/w (XLOGP3) :	2.35
Log Po/w (WLOGP) :	2.7
Log Po/w (MLOGP) :	2.04
Log Po/w (SILICOS-IT) :	2.47
Consensus Log Po/w :	2.22

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.35
Solubility :	0.114 mg/ml ; 0.000451 mol/l
Class :	Soluble
Log S (Ali) :	-3.04
Solubility :	0.228 mg/ml ; 0.000904 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 :	1.38

Safety of [ 928839-62-7 ]

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

Application In Synthesis of [ 928839-62-7 ]

* 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 [ 928839-62-7 ]
Downstream synthetic route of [ 928839-62-7 ]

[ 928839-62-7 ] Synthesis Path-Upstream 1~6

1
[ 74316-55-5 ]
[ 928839-62-7 ]

Yield	Reaction Conditions	Operation in experiment
62%	With chromium(VI) oxide; sulfuric acid In water at 90℃; for 2 h;	Step 2: S-bromoquinoline-S-carboxylic acidA solution (0.1 M) of 5-bromo-8-methylquinoline (from Step 1) in H2SOzrH2O (3:2) was treated with Cr?3 (10 eq.) at 900C. The reaction mixture was heated at 900C for 2 h. Then, the mixture was poured into ice and the precipitate was filtered affording (62percent) the title compound as an orange solid; MS (ES+) m/z 252, 254 (M+H)+.

Reference： [1] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 8, p. 2836 - 2848
[2] Patent: WO2007/28789, 2007, A1, . Location in patent: Page/Page column 34
[3] Patent: WO2013/96194, 2013, A1,
[4] Patent: WO2015/84842, 2015, A1, . Location in patent: Paragraph 0089
[5] Patent: WO2009/141386, 2009, A1, . Location in patent: Page/Page column 162; 163

2
[ 885267-41-4 ]
[ 928839-62-7 ]

Reference： [1] Patent: WO2013/96194, 2013, A1, . Location in patent: Page/Page column 32

3
[ 611-32-5 ]
[ 928839-62-7 ]

Reference： [1] Patent: WO2013/96194, 2013, A1,
[2] Patent: WO2009/141386, 2009, A1,

4
[ 1309959-33-8 ]
[ 928839-62-7 ]

Reference： [1] Patent: WO2013/96194, 2013, A1,

5
[ 20776-50-5 ]
[ 56-81-5 ]
[ 928839-62-7 ]

Reference： [1] Journal of Organic Chemistry, 2013, vol. 78, # 17, p. 8217 - 8231

6
[ 928839-62-7 ]
[ 74-88-4 ]
[ 1445781-45-2 ]

Yield	Reaction Conditions	Operation in experiment
20.5 g	With potassium carbonate In N,N-dimethyl-formamide at 45℃; for 36 h;	[0090] (b) K₂C0₃ (61.3 g, 444.0 mmol) and methyl iodide (63.1 g, 444.0 mmol) were added to a stirred suspension of 5-bromoquinoline-8-carboxylic acid (28.0 g, 111.0 mmol) in DMF (250 mL) at r.t. The reaction mixture was heated at 45 ⁰ C for 36 h, cooled to r.t, filtered the solids, washed with ethyl acetate (100 mL). The filtrate was diluted with water, extracted with ethyl acetate (3 x 300 mL) and washed with water (3 x 100 mL). The ethyl acetate layer was dried (Na₂S0₄), filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate in hexanes (0-20percent) to afford methyl-5-bromoquinoline-8-carboxylate as a cream color solid (20.5 g, 70 percent for 2 steps). 1H NMR (400 MHz, CDC1₃) δ 9.07 (dd, J = 4.3, 1.5 Hz, 1 H), 8.60 (dd, J = 8.7, 1.6 Hz, 1 H), 7.88 (s, 2 H), 7.58 (dd, J = 8.6, 4.0 Hz, 1 H), 4.05 (s, 3 H)

Reference： [1] Patent: WO2013/96194, 2013, A1, . Location in patent: Page/Page column 33
[2] Patent: WO2015/84842, 2015, A1, . Location in patent: Paragraph 0090

[ 928839-62-7 ] Synthesis Path-Downstream 1~25

1
[ 928839-62-7 ]
[ 108-42-9 ]
5-bromo-N-(3-chlorophenyl)-quinoline-8-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 20℃; for 16.0h;	Step 3: 5-bromo-N-(3-chlorophenyl)-l,2,3,4-tetrahvdroquinoline-8-carboxamide A solution (0.3 M) of <strong>[928839-62-7]5-bromoquinoline-8-carboxylic acid</strong> (from Step 2) in CH2Cl2 was treated withDIPEA (4.4 eq.), 3-chloroaniline (1.1 eq.), and HATU (1.1 eq.). The reaction mixture was stirred at RT for 16 h. Then, it was treated with IN HCl, the resulting precipitate was filtered and the organic phase separated. The organic phase was then washed with IN HCl, aqueous NaHC?3 (saturated solution) and dried. Evaporation of the solvent gave a crude that was washed with Et2O and filtered affording a solid that was dissolved in THF. The resulting solution (0.1 M) was treated with NaCNBH3 (2.0 eq) andBF3. Et2O (1.5 eq.). The reaction mixture was heated at 8O0C for 2 h and then, more NaBH3CN (3.0 eq.) and BF3. Et2O (3.0 eq.) were added. After heating the reaction mixture at 8O0C for another 2 h, it was left to cool down and then treated with NH3 and the aqueous phase extracted with EtOAc. The combined organic layers were dried and evaporated to give a crude which was resubmitted to the same reaction conditions to afford (87%) the title compound as a solid; MS (ES+) m/z 365, 367 (M+H)+.

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 2836 - 2848
[2]Patent: WO2007/28789,2007,A1 .Location in patent: Page/Page column 34

2
[ 74316-55-5 ]
[ 928839-62-7 ]

Yield	Reaction Conditions	Operation in experiment
62%	With chromium(VI) oxide; sulfuric acid; In water; at 90℃; for 2.0h;	Step 2: S-bromoquinoline-S-carboxylic acidA solution (0.1 M) of 5-bromo-8-methylquinoline (from Step 1) in H2SOzrH2O (3:2) was treated with Cr?3 (10 eq.) at 900C. The reaction mixture was heated at 900C for 2 h. Then, the mixture was poured into ice and the precipitate was filtered affording (62%) the title compound as an orange solid; MS (ES+) m/z 252, 254 (M+H)+.
	With chromium(VI) oxide; sulfuric acid; In water; at 70 - 80℃; for 3.5h;	[0089] (a) To a stirred solution of H20 (80 mL) and H2S04 (120 mL) at 0 0 C was added 5- bromo-8-methylquinoline (25 g, 112.6 mmol). After obtaining a solution, Cr03 was introduced (16 g, 157.6 mmol) in portion wise while maintaining the internal temperature at 70 C. The reaction mixture was stirred for 1 h at 70 C. An additional Cr03 (16 g, 157.6 mmol) was added in portions and stirred at 80 C for 2.5 h. After completion of the reaction, it was cooled to r.t, poured onto crushed ice, neutralized with aqueous ammonium hydroxide to get the solids. The solids were filtered, dried under high vacuum for 16 h to get the crude 5-bromoquinoline-8-carboxylic acid (28.0 g) as a green colored solid.
	With potassium permanganate; In pyridine; ethanol; at 110℃; for 0.166667h;	A solution of potassium permanganate (18.2 g, 1 15.5 mmol, 2 equiv) in H2O (200 ml.) was added to a hot (1 10C) solution of 5-bromo-8-methyl-quinoline (Step 159.4) (12.8 g, 57.7 mmol) in pyridine (120 ml_). The reaction mixture was stirred for 10 min at 1 10C and filtered while hot. The residue in the filter was washed with H2O and pyridine. The filtrate was concentrated to remove pyridine, diluted with Et2O and basified by addition of a 2 N aqueous solution of NaOH (20 ml_). The aqueous layer was separated and made acidic (pH 3) by addition of a 2 N aqueous solution of HCI. The resulting precipitate was collected by vacuum filtration to provide 1.45 g of the title compound as a green solid: ESI-MS: 251.9 / 253.9 [M+H]+; tR= 3.56 min (System 1 ).

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 2836 - 2848
[2]Patent: WO2007/28789,2007,A1 .Location in patent: Page/Page column 34
[3]Patent: WO2013/96194,2013,A1
[4]Patent: WO2015/84842,2015,A1 .Location in patent: Paragraph 0089
[5]Patent: WO2009/141386,2009,A1 .Location in patent: Page/Page column 162; 163

3
[ 928839-62-7 ]
[ 928839-65-0 ]

Yield	Reaction Conditions	Operation in experiment
20%	With hydrogenchloride; hydrogen;platinum(IV) oxide; In 1,4-dioxane; methanol; for 0.5h;	Step 3: 5-bromo-l,2,3,4-tetrahvdroquinoline-8-carboxylic acid To a solution (0.2 M) of <strong>[928839-62-7]5-bromoquinoline-8-carboxylic acid</strong> (prepared as in Example 6, Step 2) inMeOH/HCl (4 M in dioxane) (1 :1, v/v), PtO2 (0.3 eq.) was added. The reaction mixture was stirred under H2 atmosphere for 30 min. The reaction mixture was filtered over celite. After evaporation of the solvent the residue was purified on flash column chromatography reverse phase (MeCN/water, 1 :1) affording (20%) of the title compound as a solid; MS (ES+) m/z 256, 258 (M+H)+.

Reference： [1]Patent: WO2007/28789,2007,A1 .Location in patent: Page/Page column 35-36

4
[ 928839-62-7 ]
[ 192182-54-0 ]
[ 1197333-36-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In ethanol; water; toluene; at 105℃; for 1.0h;Inert atmosphere;	A mixture of 3,5-dimethoxyphenylboronic acid (217 mg, 1.19 mmol, 1.2 equiv) (Step 1.8) inEtOH (0.5 ml.) was added dropwise to a mixture of delta-bromo-quinoline-delta-carboxylic acid <n="164"/>(Step 159.3) (250 mg, 0.99 mmol), PdCI2(dppf) (22mg, 0.03 mmol, 0.03 equiv), Na2CO3 (2M solution in H2O, 1 ml_, 3.97mmol, 4equiv) in toluene (5ml_) at 1050C, under an argon atmosphere. The reaction mixture was stirred at 1050C for 1 h, allowed to cool to rt, diluted with EtOAc and H2O, basified by addition of a 2N aqueous solution of NaOH (2ml_), filtered through a pad of celite and the filtrate was extracted with EtOAc. The aqueous layer was separated and acidified to pH 5. The resulting precipitate was collected by vacuum filtration to provide 248mg of the title compound as a white solid: ESI-MS:310.1 [M+H]+; tR=4.06min (System 1 ).

Reference： [1]Patent: WO2009/141386,2009,A1 .Location in patent: Page/Page column 162-163

5
[ 928839-62-7 ]
[ 21961-31-9 ]
C₁₈H₁₂BrClN₂O₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 2836 - 2848

6
[ 611-32-5 ]
[ 928839-62-7 ]

Reference： [1]Patent: WO2013/96194,2013,A1
[2]Patent: WO2009/141386,2009,A1

7
[ 1309959-33-8 ]
[ 928839-62-7 ]

Reference： [1]Patent: WO2013/96194,2013,A1

8
[ 885267-41-4 ]
[ 928839-62-7 ]

Yield	Reaction Conditions	Operation in experiment
	With silver nitrate; sodium hydroxide; In tetrahydrofuran; water; at 20℃; for 0.5h;	To a solution of 5-Bromoquinoline-8-carbaldehyde (10 g, 0.039mol) in THF (300ml) was added aquous NaOH (30 g) and followed by silver nitrate (10.79 g, 0.0635 mol) lot wise at RT for 10 min and this reaction mixture was stirred at RT for 30min.The reaction completion was confirmed by TLC. After completion of reaction the reaction mixture was filtered. The black solid was wahded with THF, MeOH and DMF (50ml each). (Note: Product was not soluble in any of these solvents The filtrate and washings were discarded). The black solid was dried to afford the title compound (crude -30 g). The crude product was as such taken for the next step. 1H NMR (DMSO-d6, 400MHz): delta 8.92-8.91 (dd, J=4.12, 5.8Hz, 1 H), 8.49 (s, 1 H), 8.46-8.44 (dd, J=8.56, 10.2Hz, 1 H), 7.83-7.81 (dd, J=7.6, Hz, 1 H), 7.63-7.6 (dd, J=8.52, 12.68Hz, 1 H), 7.46-7.44 (d, J=7.6Hz, 1 H).

Reference： [1]Patent: WO2013/96194,2013,A1 .Location in patent: Page/Page column 32

9
[ 928839-62-7 ]
[ 1445781-87-2 ]

Reference： [1]Patent: WO2013/96194,2013,A1

10
[ 928839-62-7 ]
[ 1445781-88-3 ]

Reference： [1]Patent: WO2013/96194,2013,A1

11
[ 928839-62-7 ]
[ 1445781-89-4 ]

Reference： [1]Patent: WO2013/96194,2013,A1

12
[ 928839-62-7 ]
[ 74-88-4 ]
[ 1445781-45-2 ]

Yield	Reaction Conditions	Operation in experiment
20.5 g	With potassium carbonate; In N,N-dimethyl-formamide; at 45℃; for 36.0h;	[0090] (b) K2C03 (61.3 g, 444.0 mmol) and methyl iodide (63.1 g, 444.0 mmol) were added to a stirred suspension of 5-bromoquinoline-8-carboxylic acid (28.0 g, 111.0 mmol) in DMF (250 mL) at r.t. The reaction mixture was heated at 45 0 C for 36 h, cooled to r.t, filtered the solids, washed with ethyl acetate (100 mL). The filtrate was diluted with water, extracted with ethyl acetate (3 x 300 mL) and washed with water (3 x 100 mL). The ethyl acetate layer was dried (Na2S04), filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate in hexanes (0-20%) to afford methyl-5-bromoquinoline-8-carboxylate as a cream color solid (20.5 g, 70 % for 2 steps). 1H NMR (400 MHz, CDC13) delta 9.07 (dd, J = 4.3, 1.5 Hz, 1 H), 8.60 (dd, J = 8.7, 1.6 Hz, 1 H), 7.88 (s, 2 H), 7.58 (dd, J = 8.6, 4.0 Hz, 1 H), 4.05 (s, 3 H)

Reference： [1]Patent: WO2013/96194,2013,A1 .Location in patent: Page/Page column 33
[2]Patent: WO2015/84842,2015,A1 .Location in patent: Paragraph 0090

13
[ 928839-62-7 ]
[ 1442660-41-4 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 8217 - 8231

14
[ 928839-62-7 ]
[ 108-95-2 ]
[ 1442660-30-1 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 8217 - 8231

15
[ 20776-50-5 ]
[ 56-81-5 ]
[ 928839-62-7 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 8217 - 8231

16
[ 928839-62-7 ]
methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline-8-carboxylate [ No CAS ]

Reference： [1]Patent: WO2015/84842,2015,A1

17
[ 928839-62-7 ]
5-[6-[(4-tert-butyl-3-fluorophenyl)sulfonylamino]-2,2-difluoro-1,3-benzodioxol-5-yl]quinoline-8-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2015/84842,2015,A1

18
[ 928839-62-7 ]
5-[6-[(4-tert-butyl-3-fluorophenyl)sulfonylamino]-2,3-dichlorophenyl]quinoline-8-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2015/84842,2015,A1

19
[ 928839-62-7 ]
[ 1197333-39-3 ]