[ CAS No. 35048-10-3 ] {[proInfo.proName]}

Name: 35048-10-3|7-Fluoroquinolin-8-ol|98%
Brand: Ambeed
SKU: A132713
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Quality Control of [ 35048-10-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 35048-10-3 ]

CAS No. :	35048-10-3	MDL No. :	MFCD12024552
Formula :	C₉H₆FNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LDCRHJNNQVTBNY-UHFFFAOYSA-N
M.W :	163.15	Pubchem ID :	21823020
Synonyms :

Calculated chemistry of [ 35048-10-3 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	43.72
TPSA :	33.12 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) :	-5.92 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.65
Log Po/w (XLOGP3) :	1.93
Log Po/w (WLOGP) :	2.5
Log Po/w (MLOGP) :	1.61
Log Po/w (SILICOS-IT) :	2.38
Consensus Log Po/w :	2.01

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.68
Solubility :	0.338 mg/ml ; 0.00207 mol/l
Class :	Soluble
Log S (Ali) :	-2.25
Solubility :	0.919 mg/ml ; 0.00563 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.4
Solubility :	0.0657 mg/ml ; 0.000403 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.62

Safety of [ 35048-10-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P273	UN#:	N/A
Hazard Statements:	H302-H412	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 35048-10-3 ]

* 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 [ 35048-10-3 ]
Downstream synthetic route of [ 35048-10-3 ]

[ 35048-10-3 ] Synthesis Path-Upstream 1~3

1
[ 53981-25-2 ]
[ 56-81-5 ]
[ 35048-10-3 ]

Yield	Reaction Conditions	Operation in experiment
59%	With sulfuric acid In nitrobenzene at 140℃; for 6 h; Sealed tube; Inert atmosphere	To a solution of 2-amino-6-fluoro-phenol (2000 mg, 15.73 mmol) and nitrobenene (10 ml) in a sealable reaction pressure vessel was added in portions sulfuric acid (2 mL, 37.52 mmol). Glycerol (4.8 mL, 65.15 mmol) was added in one portion, and the solution turned to dark brown. The vessel was flushed with nitrogen, sealed and heated to 140 °C for 6 hours. The reaction mixture was cooled to ambient, diluted with (30 mL) ice/water mixture, extracted (2 X 200 mL) methyl tert-butyl ether. The aqueous phase was neutralized to pH~6-7 by slow addition of 6N sodium hydroxide. The resulting black precipitate was collected by filtration and the water solution was extracted with ethyl acetate 3 times. The organic extracts were combined with the black precipitate, concentrated in vacuo, and purified by automated normal-phase chromatography using 0-10percent methanol/dichloromethane as an eluent. The title compound was isolated as a solid (1.56 g, 59percent yield). MS (ES+) m/z 164.9 [M+H]⁺. 1H NMR (400 MHz, DMSO-^6) δ ppm 7.43 - 7.49 (m, 1 H) 7.50 - 7.57 (m, 2 H) 8.37 (dd, J=8.21, 1.64 Hz, 1 H) 8.90 (dd, J=4.17, 1.64 Hz, 1 H) 10.26 (br. s., 1 H).
51.7%	Stage #1: With sulfuric acid In nitrobenzene at 140℃; for 6 h; Stage #2: With sodium hydroxide In water	To a solution of 2-amino-6-fluorophenol (4.0 g, 31.6 mmol) and nitrobenzene (20 mL) in a sealable reaction vessel was added in portions sulfuric acid (4.0 mL). Glycerol (12.0 g, 126 mmol) was added in one portion, and the solution turned to dark brown. The vessel was flushed with nitrogen, sealed and heated to 140 °C for 6 h. The reaction mixture was cooled to rt, diluted with 30 mL ice/water mixture, and washed 3 times with methyl -butyl ether (removes most of the nitrobenzene). The aqueous phase was neutralized to pH=6-7 by slow addition of 6N NaOH. The resulting black precipitate was collected and the water solution was extracted with ethyl acetate 3 times. The organic extracts were combined with the black precipitate, concentrated in vacuo, and purified on silica gel column with 0-10percent MeOH/DCM to give 2.67 g (51.7percent) of 7-fluoro-8-quinolinol as an off-white solid.

Reference： [1] Patent: WO2016/123576, 2016, A1, . Location in patent: Paragraph 0276
[2] Patent: WO2012/20389, 2012, A1, . Location in patent: Page/Page column 40-41

2
[ 3054-95-3 ]
[ 53981-25-2 ]
[ 35048-10-3 ]

Yield	Reaction Conditions	Operation in experiment
43%	With hydrogenchloride In water at 111℃; for 24 h;	General procedure: A 1N HCl solution (82.5 mL) was added to the aniline (~1 mmol) in a round bottom flask. To this was added acrolein diethyl acetal (2.5 mmol). The resulting solution was refluxed at 111 °C for 24 hours. After cooling to room temperature, the solution was neutralized (pH 7−8) by addition of solid Na2CO3. The product was then extracted into dichloromethane (3 x 100 mL), and the combined organic layers were dried over Na2SO4 and evaporated under reduced pressure. The crude residue was then purified by column chromatography (elution mixture of hexane with ethyl acetate or 15percent ethyl acetate/cyclohexane with methanol) to give the desired quinoline product.

Reference： [1] Tetrahedron Letters, 2015, vol. 56, # 46, p. 6436 - 6439

3
[ 1526-17-6 ]
[ 56-81-5 ]
[ 35048-10-3 ]

Reference： [1] Chemical Communications, 2006, # 18, p. 1941 - 1943

[ 35048-10-3 ] Synthesis Path-Downstream 1~36

2
[ 1526-17-6 ]
[ 56-81-5 ]
[ 35048-10-3 ]

Reference： [1]Chemical Communications,2006,p. 1941 - 1943

3
[ 35048-10-3 ]
[ 555-31-7 ]
[ 260062-14-4 ]

Reference： [1]Chemical Communications,2006,p. 1941 - 1943

4
[ 53981-25-2 ]
[ 56-81-5 ]
[ 35048-10-3 ]

Yield	Reaction Conditions	Operation in experiment
59%	With sulfuric acid; In nitrobenzene; at 140℃; for 6h;Sealed tube; Inert atmosphere;	To a solution of 2-amino-6-fluoro-phenol (2000 mg, 15.73 mmol) and nitrobenene (10 ml) in a sealable reaction pressure vessel was added in portions sulfuric acid (2 mL, 37.52 mmol). Glycerol (4.8 mL, 65.15 mmol) was added in one portion, and the solution turned to dark brown. The vessel was flushed with nitrogen, sealed and heated to 140 C for 6 hours. The reaction mixture was cooled to ambient, diluted with (30 mL) ice/water mixture, extracted (2 X 200 mL) methyl tert-butyl ether. The aqueous phase was neutralized to pH~6-7 by slow addition of 6N sodium hydroxide. The resulting black precipitate was collected by filtration and the water solution was extracted with ethyl acetate 3 times. The organic extracts were combined with the black precipitate, concentrated in vacuo, and purified by automated normal-phase chromatography using 0-10% methanol/dichloromethane as an eluent. The title compound was isolated as a solid (1.56 g, 59% yield). MS (ES+) m/z 164.9 [M+H]+. 1H NMR (400 MHz, DMSO-^6) delta ppm 7.43 - 7.49 (m, 1 H) 7.50 - 7.57 (m, 2 H) 8.37 (dd, J=8.21, 1.64 Hz, 1 H) 8.90 (dd, J=4.17, 1.64 Hz, 1 H) 10.26 (br. s., 1 H).
51.7%		To a solution of 2-amino-6-fluorophenol (4.0 g, 31.6 mmol) and nitrobenzene (20 mL) in a sealable reaction vessel was added in portions sulfuric acid (4.0 mL). Glycerol (12.0 g, 126 mmol) was added in one portion, and the solution turned to dark brown. The vessel was flushed with nitrogen, sealed and heated to 140 C for 6 h. The reaction mixture was cooled to rt, diluted with 30 mL ice/water mixture, and washed 3 times with methyl -butyl ether (removes most of the nitrobenzene). The aqueous phase was neutralized to pH=6-7 by slow addition of 6N NaOH. The resulting black precipitate was collected and the water solution was extracted with ethyl acetate 3 times. The organic extracts were combined with the black precipitate, concentrated in vacuo, and purified on silica gel column with 0-10% MeOH/DCM to give 2.67 g (51.7%) of 7-fluoro-8-quinolinol as an off-white solid.

Reference： [1]Patent: WO2016/123576,2016,A1 .Location in patent: Paragraph 0276
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 9647 - 9665
[3]Patent: WO2012/20389,2012,A1 .Location in patent: Page/Page column 40-41

5
[ 35048-10-3 ]
C₁₆H₁₆FNO [ No CAS ]

Reference： [1]Patent: WO2012/20389,2012,A1

6
[ 35048-10-3 ]
7-fluoro-5-[2-(methyl-2-propyn-1-ylamino)ethyl]-8-quinolinol [ No CAS ]

Reference： [1]Patent: WO2012/20389,2012,A1

7
[ 35048-10-3 ]
[ 38453-31-5 ]

Yield	Reaction Conditions	Operation in experiment
97%	With bromine; acetic acid; at 20℃; for 16.0h;	An rt solution of bromine (2.34 g, 14.7 mmol) in acetic acid (10 mL) was slowly added to a solution of <strong>[35048-10-3]7-fluoro-8-quinolinol</strong> (2.0 g, 12.2 mmol) in acetic acid (30 mL). The brown reaction mixture was stirred at rt for 16 h, after which the mixture was quenched with saturated sodium bisulfite solution. The resulting mixture was extracted with methyl t- butyl ether 3 times. The combined organic phases were washed with saturated NaHC03 and brine, dried over Na2S04, and concentrated in vacuo to dryness to give 3.0 g (97.0%) 5-bromo-<strong>[35048-10-3]7-fluoro-8-quinolinol</strong> as a green solid.
70%	With bromine; iron; In chloroform; at 5℃;Inert atmosphere; Cooling with ice;	(1) Under a nitrogen atmosphere, to 150mL three-necked flask was added Compound A (7- fluoro-8-hydroxyquinoline) (2.1g, 12.80mmol),Iron powder (11.0mg, 0.19mmol) and 50mL of chloroform, cooled with ice water bath;5 mL of a liquid bromine (3.7 g, 23.37 mmol) / trichloromethane mixed solution was added dropwise, and the temperature in the bottle did not exceed 5 C. during the dropwise addition.After the reaction was completed, filtration and recrystallization from chloroform gave yellow solid B (5-bromo-<strong>[35048-10-3]7-fluoro-8-hydroxyquinoline</strong>) (2.2 g, yield 70%)
41%	With N-Bromosuccinimide; In chloroform; at 40℃;	N-Bromosuccinimide (130 mg, 0.73 mmol) was added to a solution of 7-fluoro-8- hydroxyquinoline (98 mg, 0.60 mmol) in chloroform (5 mL). The reaction mixture was stirred and heated to 40 C overnight and then diluted with DCM (50 ml) and washed with 15% sodium thiosulfate solution (3 x 10 mL). The organic layer was dried (Na2S04) and solvent evaporated to give a brown solid. Chromatography of the residue (0?25% EtOAc / hexanes gradient) gave 60 mg of the title product. Yield: 41%. Pale yellow solid. NMR (400 MHz, CDCh): delta 8.83 (dd, J= 1.3, 4.3 Hz, 1H), 8.46 (dd, J= 1.5, 8.6 Hz, 1H), 7.71 (d, J= 10.3 Hz, 1H), 7.54 (dd, J = 4.3, 8.6 Hz, lH) ppm. 13C NMR (101 MHz, CDCh): delta 149.3, 146.7 (d, J= 248.0 Hz), 139.7 (d, J = 7.6 Hz), 138.2 (d, J= 10.5 Hz), 135.9 (d, J= 2.0 Hz), 124.4, 122.1, 121.9 (d, J= 20.1 Hz), 109.3 (d, J= 9.8 Hz) ppm. LRMS (ESI) cacld. C9H6BrFNO [M + H]+ 241.96, found 242.10. HRMS (ESI) C9H6BrFNO calcd. [M + H]+ 241.9617, found 241.9615. HPLC purity (MeCN / H20 / 0.1% TFA): 97.9%, 9.9 mm; HPLC purity (MeOH / H20 / 0.1% TFA): 98.6%, 17.8 mm.

Reference： [1]Patent: WO2012/20389,2012,A1 .Location in patent: Page/Page column 41
[2]Patent: CN110790760,2020,A .Location in patent: Paragraph 0032-0035
[3]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 1025 - 1029
[4]Patent: WO2017/27064,2017,A1 .Location in patent: Page/Page column 108

8
[ 35048-10-3 ]
[ 1357913-92-8 ]

Reference： [1]Patent: WO2012/20389,2012,A1

9
[ 35048-10-3 ]
[ 1357913-93-9 ]

Reference： [1]Patent: WO2012/20389,2012,A1

10
[ 35048-10-3 ]
C₁₃H₁₂FNO₃ [ No CAS ]

Reference： [1]Patent: WO2012/20389,2012,A1

11
[ 35048-10-3 ]
[ 38453-30-4 ]

Yield	Reaction Conditions	Operation in experiment
36%	With N-chloro-succinimide; In dichloromethane; at 20 - 40℃; for 53.0h;	N-Chlorosuccinimide (120 mg, 0.90 mmol) was added to a solution of 7-fluoro-8- hydroxyquinoline (120 mg, 0.74 mmol) in DCM (5 mL). The reaction mixture was stirred and heated to 40 C for 5 h and then cooled to rt for 2 days. The reaction was then diluted with DCM (50 ml) and washed with 15% sodium thiosulfate solution (3 x 10 mL). The organic layer was dried (Na2S04) and solvent evaporated to give a brown solid. Chromatography of the residue (0?20% EtOAc / hexanes gradient) gave 52 mg of the title product. Yield: 36%. White solid. NMR (400 MHz, CDCh): 5 8.86 (dd, J= 1.2, 4.2 Hz, 1H), 8.51 (dd, J= 1.6, 8.9 Hz, 1H), 7.54 (dd, J= 4.4, 8.9 Hz, 1H), 7.51 (d, J= 10.5 Hz, 1H) ppm. 13C NMR (400 MHz, CDCh): delta 149.50, 146.6 (d, J= 246.5 Hz), 139.6 (d, J= 7.9 Hz), 137.7 (d, J= 10.4 Hz), 133.5 (d, J= 2.3 Hz), 123.3, 121.8 (d, J= 3.1 Hz), 120.5 (d, J= 10.1 Hz), 118.7 (d, J= 24.5 Hz) ppm. LRMS (ESI) calcd. for C9H6C1FN0 [M + H]+ 198.01, found 198.10. HRMS (ESI) calcd. C9H6C1FN0 [M + H]+ 198.0122, found 198.0120. HPLC purity (MeCN / H20 / 0.1% TFA): 99.8%, 7.5 mm; HPLC purity (MeOH / H20 / 0.1% TFA): 99.6%, 10.4 mm.

Reference： [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 1025 - 1029
[2]Patent: WO2017/27064,2017,A1 .Location in patent: Page/Page column 107; 108

12
[ 35048-10-3 ]
[ 38453-32-6 ]

Yield	Reaction Conditions	Operation in experiment
97%	With N-iodo-succinimide; In chloroform; at 40℃; for 0.25h;	A solution of <strong>[35048-10-3]7-fluoroquinolin-8-ol</strong> (250 mg, 1.53 mmol) and N-iodosuccinimide (413.69 mg, 1.84 mmol) in chloroform was vigorously stirred at 40 C. After 15 minutes the reaction was diluted with dichlorom ethane, extracted (2 X 20 mL) 10% sodium thiosulfate solution and dried over sodium sulfate. The pale yellow solids were taken on in subsequent reactions without additional purification. (429.6 mg, 97% yield). MS (ES+) m/z 290.9 [M+H]+.1H NMR (400 MHz, DMSO-^6) delta ppm 7.67 (dd, J=8.59, 4.29 Hz, 1 H) 8.17 (d, J=10.61 Hz, 1 H) 8.25 - 8.35 (m, 1 H) 8.90 (dd, J=4.04, 1.52 Hz, 1 H) 10.62 (br. s., 1 H).
87%	With N-iodo-succinimide; In chloroform; at 40℃; for 0.5h;	101291 A solution of <strong>[35048-10-3]7-fluoroquinolin-8-ol</strong> (5 g, 30.6 mmol) and N-iodosuccinimide (8.3 g, 36.7 mmol) in chloroform was vigorously stirred at 40 C. After 30 minutes the reaction was diluted with dichloromethane, extracted (2 X 20 ml) 10% sodium thiosulfate solution and dried over sodium sulfate. The orange solids (7.76 g, 87%) were taken on in subsequent reactions without additional purification. MS (ES+) m/z 289.9 [M+H]. ?H NMR (400 IVIHz, CDC13) oe ppm 7.49 - 7.56 (m, 1 H), 7.97 (d, J=9.85 Hz, 1 H), 8.32 (dd, J=8.46, 1.39 Hz, 1 H), 8.79 (dd, J=4.29, 1.52 Hz, 1 H).
53%	With N-iodo-succinimide; In chloroform;Reflux;	N-iodosuccinimide (166 mg, 0.74 mmol) was added to a solution of 7-fluoro-8- hydroxyquinoline (100 mg, 0.61 mmol) in chloroform (10 mL). The reaction mixture was stirred and heated to reflux overnight and then diluted with DCM (50 ml) and washed with 15% sodium thiosulfate solution (3 x 10 mL). The organic layer was dried (Na2S04) and solvent evaporated to give a brown solid. Chromatography of the residue (0?20% EtOAc / hexanes gradient) gave 93 mg of the title product. Yield: 53%. Pale yellow solid. NMR (400 MHz, CDCh): delta 8.77 (dd, J = 1.3, 4.2 Hz, 1H), 8.30 (dd, J= 1.4, 8.6 Hz, 1H), 7.95 (d, J= 10.1 Hz, 1H), 7.51 (dd, J= 4.2, 8.6 Hz, lH) ppm. 13C NMR (101 MHz, CDCh): delta 149.2, 147.2 (d, J = 246.6 Hz), 145.9, 140.4 (d, J = 2.0 Hz), 139.5 (d, J= 7.4 Hz), 139.1 (d, J= 10.2 Hz), 128.7 (d, J = 23.9 Hz), 126.9 (d, J= 1.4 Hz), 122.5 (d, J= 2.5 Hz), 82.7 (d, J= 8.8 Hz) ppm. LRMS (ESI) cacld. C9H6FINO [M + H]+ 289.95, found 289.58. HRMS (ESI) cacld. C9H6FINO [M + H]+ 289.9478, found 289.9476. HPLC purity (MeCN / H20 / 0.1% TEA): 96.8%, 8.8 mm; HPLC purity (MeOH / H20 / 0.1% TFA): 96.5%, 12.1 mm.

Reference： [1]Patent: WO2016/123576,2016,A1 .Location in patent: Paragraph 0277
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 9647 - 9665
[3]Patent: WO2016/123577,2016,A1 .Location in patent: Paragraph 0129
[4]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 1025 - 1029
[5]Patent: WO2017/27064,2017,A1 .Location in patent: Page/Page column 109

13
[ 3054-95-3 ]
[ 53981-25-2 ]
[ 35048-10-3 ]

Yield	Reaction Conditions	Operation in experiment
43%	With hydrogenchloride; In water; at 111℃; for 24h;	General procedure: A 1N HCl solution (82.5 mL) was added to the aniline (~1 mmol) in a round bottom flask. To this was added acrolein diethyl acetal (2.5 mmol). The resulting solution was refluxed at 111 C for 24 hours. After cooling to room temperature, the solution was neutralized (pH 7-8) by addition of solid Na2CO3. The product was then extracted into dichloromethane (3 x 100 mL), and the combined organic layers were dried over Na2SO4 and evaporated under reduced pressure. The crude residue was then purified by column chromatography (elution mixture of hexane with ethyl acetate or 15% ethyl acetate/cyclohexane with methanol) to give the desired quinoline product.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 6436 - 6439

14
[ 123-75-1 ]
[ 35048-10-3 ]
[ 76-05-1 ]
7-fluoro-5-pyrrolidin-1-ylsulfonylquinolin-8-ol trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%		To a suspension of in <strong>[35048-10-3]7-fluoroquinolin-8-ol</strong> (0.12 mL, 0.92 mmol) in 5 ml dichloroethane was added chlorosulfonic acid (20 drops) at ambient temperature. The resultant solution was heated to reflux overnight. The reaction mixture was cooled to 0C and pyrrolidine (1 mL, 12.18 mmol) was added. The reaction mixture was allowed to warm to ambient temperature and concentrated to a residue. Purification was accomplished by reversed phase HPLC eluting 10-100%) acetonitrile/water with 0.05%> trifluoroacetic acid as modifier. The product containing fractions were pooled and concentrated to a tan solid (123.4 mg, 33%>) as the trifluoroacetic acid salt. MS (ES+) m/z 297.1 [M+H]. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.71 (dt, J=6.51, 3.44 Hz, 4 H) 3.17 - 3.23 (m, 4 H) 7.77 (dd, J=8.84, 4.04 Hz, 1 H) 8.09 (d, J=10.86 Hz, 1 H) 9.03 (dd, J=4.17, 1.39 Hz, 1 H) 9.07 (dd, J=8.84, 1.52 Hz, 1 H).

Reference： [1]Patent: WO2016/123576,2016,A1 .Location in patent: Paragraph 0291

15
[ 35048-10-3 ]
8-benzyloxy-7-fluoro-5-iodo-quinoline [ No CAS ]

Reference： [1]Patent: WO2016/123576,2016,A1
[2]Patent: WO2016/123577,2016,A1
[3]Journal of Medicinal Chemistry,2018,vol. 61,p. 9647 - 9665

16
[ 35048-10-3 ]
8-benzyloxy-7-fluoro-5-(p-tolylsulfanyl)quinoline [ No CAS ]

Reference： [1]Patent: WO2016/123576,2016,A1
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 9647 - 9665

17
[ 35048-10-3 ]
8-benzyloxy-7-fluoro-5-(p-tolylsulfonyl)quinoline [ No CAS ]

Reference： [1]Patent: WO2016/123576,2016,A1
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 9647 - 9665

18
[ 35048-10-3 ]
7-fluoro-5-(p-tolylsulfonyl)quinolin-8-ol [ No CAS ]

Reference： [1]Patent: WO2016/123576,2016,A1
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 9647 - 9665

19
[ 35048-10-3 ]
[ 70931-28-1 ]
7-fluoro-5-[4-[(4-fluorophenyl)methyl]piperazin-1-yl]sulfonylquinolin-8-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a suspension of in <strong>[35048-10-3]7-fluoroquinolin-8-ol</strong> (0.12 mL, 0.92 mmol) in 5 ml dichloroethane was added chlorosulfonic acid (20 drops) at ambient temperature. The resultant solution was heated to reflux overnight. The reaction mixture was cooled to 0C and pyrrolidine (1 mL, 12.18 mmol) was added. The reaction mixture was allowed to warm to ambient temperature and concentrated to a residue. Purification was accomplished by reversed phase HPLC eluting 10-100%) acetonitrile/water with 0.05%> trifluoroacetic acid as modifier. The product containing fractions were pooled and concentrated to a tan solid (123.4 mg, 33%>) as the trifluoroacetic acid salt. MS (ES+) m/z 297.1 [M+H]. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.71 (dt, J=6.51, 3.44 Hz, 4 H) 3.17 - 3.23 (m, 4 H) 7.77 (dd, J=8.84, 4.04 Hz, 1 H) 8.09 (d, J=10.86 Hz, 1 H) 9.03 (dd, J=4.17, 1.39 Hz, 1 H) 9.07 (dd, J=8.84, 1.52 Hz, 1 H).

Reference： [1]Patent: WO2016/123576,2016,A1 .Location in patent: Paragraph 0291; 0292

20
[ 35048-10-3 ]
5-(cyclopentylsulfonyl)-7-fluoroquinolin-8-ol [ No CAS ]

Reference： [1]Patent: WO2016/123577,2016,A1
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 9647 - 9665

21
[ 35048-10-3 ]
8-benzyloxy-5-cyclopentylsulfanyl-7-fluoro-quinoline [ No CAS ]

Reference： [1]Patent: WO2016/123577,2016,A1
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 9647 - 9665

22
[ 35048-10-3 ]
8-benzyloxy-5-cyclopentylsulfonyl-7-fluoro-quinoline [ No CAS ]

Reference： [1]Patent: WO2016/123577,2016,A1
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 9647 - 9665

23
[ 35048-10-3 ]
8-benzyloxy-7-fluoro-5-[4-(trifluoromethyl)phenyl]sulfanylquinoline [ No CAS ]