[ CAS No. 36748-99-9 ] {[proInfo.proName]}

Name: 36748-99-9|7-Bromo-8-methoxyquinoline|95%
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SKU: A793550
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Quality Control of [ 36748-99-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 36748-99-9 ]

Product Details of [ 36748-99-9 ]

CAS No. :	36748-99-9	MDL No. :	MFCD18452260
Formula :	C₁₀H₈BrNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UQYGSQHBIDZNBX-UHFFFAOYSA-N
M.W :	238.08	Pubchem ID :	11118102
Synonyms :

Calculated chemistry of [ 36748-99-9 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.1
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	55.94
TPSA :	22.12 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) :	-5.73 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.25
Log Po/w (XLOGP3) :	2.85
Log Po/w (WLOGP) :	3.01
Log Po/w (MLOGP) :	2.19
Log Po/w (SILICOS-IT) :	3.1
Consensus Log Po/w :	2.68

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.61
Solubility :	0.0578 mg/ml ; 0.000243 mol/l
Class :	Soluble
Log S (Ali) :	-2.97
Solubility :	0.253 mg/ml ; 0.00106 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.69
Solubility :	0.00489 mg/ml ; 0.0000206 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.72

Safety of [ 36748-99-9 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 36748-99-9 ]

* 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.

Downstream synthetic route of [ 36748-99-9 ]

[ 36748-99-9 ] Synthesis Path-Downstream 1~35

1
[ 36748-99-9 ]
[ 74-88-4 ]
7-bromo-8-methoxy-1-methyl-quinolinium; iodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 60℃;

Reference： [1]Howitz; Witte [Chemische Berichte, 1905, vol. 38, p. 1262]

2
[ 36748-99-9 ]
[ 100-52-7 ]
1-(8-methoxy-7-quinolyl)-1-phenylmethanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With hydrogenchloride; water; phenyllithium In diethyl ether 1.) -75 deg C, 2.5 h; 2.) -75 deg C, 2 h; 3.) THF, r.t.;

Reference： [1]Trecourt; Mallet; Mongin; Queguiner [Synthesis, 1995, # 9, p. 1159 - 1162]

3
[ 36748-99-9 ]
[ 938-33-0 ]

Reference： [1]Synthesis,1995,p. 1159 - 1162

4
[ 36748-99-9 ]
[ 36749-00-5 ]

Yield	Reaction Conditions	Operation in experiment
70%	With hydrogenchloride; water; iodine; phenyllithium In diethyl ether 1.) -75 deg C, 2.5 h; 2.) -75 deg C, 2 h; 3.) THF, r.t.;

Reference： [1]Trecourt; Mallet; Mongin; Queguiner [Synthesis, 1995, # 9, p. 1159 - 1162]

5
[ 36748-99-9 ]
7-deuterio-8-methoxyquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With hydrogenchloride; diclazuril; water; water-d2; phenyllithium In diethyl ether 1.) -75 deg C, 2.5 h; 2.) -75 deg C, 2 h; 3.) THF, r.t.;

Reference： [1]Trecourt; Mallet; Mongin; Queguiner [Synthesis, 1995, # 9, p. 1159 - 1162]

6
[ 36748-99-9 ]
7-hydroxy-8-methoxyquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With peracetic acid; Trimethyl borate; sodium hydrogensulfite; phenyllithium In diethyl ether 1.) -75 deg C, 2.5 h; 2.) AcOH, -75 deg C, 30 min then 0 deg C, 1 h; 3.) r.t., 30 min;

Reference： [1]Trecourt; Mallet; Mongin; Queguiner [Synthesis, 1995, # 9, p. 1159 - 1162]

7
[ 13019-32-4 ]
[ 74-88-4 ]
[ 36748-99-9 ]

Yield	Reaction Conditions	Operation in experiment
100%		In an oven dried round bottom flask under nitrogen, a solution of 7-bromoquinolin- 8-ol (1 g, 4.46 mmol) in N,N-dimethylformamide (20 mL) at room temperature was treated with sodium hydride (60% dispersion in mineral oil, 0.268 g, 6.69 mmol) to give a bright yellow mixture and was stirred for 3 min. lodomethane (0.307 mL, 4.91 mmol) was then added by syringe and the reaction was stirred for 30 min. The reaction was quenched carefully with water (50 mL) and diluted with ethyl acetate (100 mL). The layers were separated and the organic layer was dried over magnesium sulfate and concentrated in vacuo to give a liquid, which solidified to a white solid (1.06 g, quantitative yield) on standing overnight. MS(ES)+ m/e 237.8, 239.7 [M+H]+.
100%		In an oven dried round bottom flask under nitrogen, a solution of <strong>[13019-32-4]7-bromoquinolin-8-ol</strong> (1g, 4.46 mmol) in N,N-dimethylformamide (20 mL) at room temperature was treated with sodium hydride (60% dispersion in mineral oil, 0.268 g,6.69 mmol) to give a bright yellow mixture and was stirred for 3 min. lodomethane (0.307 mL, 4.91 mmol) was then added by syringe and the reaction was stirred for 30 min. The reaction was quenched carefully with water (50 mL) and diluted with ethyl acetate (100 mL). The layers were separated and the organic layer was dried over magnesium sulfate and concentrated in vacuo to give a liquid, which solidified to a whitesolid (1 .06 g, quantitative yield) on standing overnight. MS(ES)+ m/e 237.8, 239.7 [M+H]+.
100%		In an oven dried round bottom flask under nitrogen, a solution of 7-bromoquinolin-8- ol (1 g, 4.46 mmol) in N,N-dimethylformamide (20 mL) at room temperature was treated with sodium hydride (60% dispersion in mineral oil, 0.268 g, 6.69 mmol) to give a bright yellow mixture and was stirred for 3 minutes. lodomethane (0.307 mL, 4.91 mmol) was then added by syringe and the reaction was stirred for 30 minutes. The reaction was quenched carefully with water (50 mL) and diluted with ethyl acetate (100 mL). The layers were separated and the organic layer was dried over magnesium sulfate and concentrated in vacuo to give a liquid, which solidified to a white solid (1.06 g, quantitative yield) on standing overnight. MS(ES)+ m/e 237.8, 239.7 [M+H]+.

Reference： [1]Patent: WO2013/28447,2013,A1 .Location in patent: Page/Page column 110
[2]Patent: WO2013/52716,2013,A1 .Location in patent: Page/Page column 53
[3]Patent: WO2014/8223,2014,A2 .Location in patent: Page/Page column 66
[4]Synthesis,1995,p. 1159 - 1162

8
[ 36748-99-9 ]
[ 146140-95-6 ]
[ 172795-87-8 ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium carbonate In ethanol; toluene for 72h; Heating;

Reference： [1]Trecourt, Francois; Mallet, Marc; Mongin, Florence; Queguiner, Guy [Tetrahedron, 1995, vol. 51, # 43, p. 11743 - 11750]

9
[ 36748-99-9 ]
5-methoxy-2-(pivaloylamino)phenylboronic acid [ No CAS ]
[ 172795-96-9 ]

Yield	Reaction Conditions	Operation in experiment
45%	With potassium carbonate In ethanol; toluene for 72h; Heating;

Reference： [1]Trecourt, Francois; Mallet, Marc; Mongin, Florence; Queguiner, Guy [Tetrahedron, 1995, vol. 51, # 43, p. 11743 - 11750]

10
[ 36748-99-9 ]
[ 88703-69-9 ]
1,2-Di(8-methoxyquinoline-7-yl)hexane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In tetrahydrofuran for 15h; Heating;

Reference： [1]Albrecht, Markus; Blau, Oliver; Witt, Karen; Wegelius, Elina; Nissinen, Maija; Rissanen, Kari; Froehlich, Roland [Synthesis, 1999, # 10, p. 1819 - 1829]

Yield	Reaction Conditions	Operation in experiment
	7-Brom-8-chinolinol, CH3I;

12
[ 74-88-4 ]
[ 36748-99-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide

Reference： [1]Howitz; Witte [Chemische Berichte, 1905, vol. 38, p. 1262]

13
[ 36748-99-9 ]
[ 171087-99-3 ]
[ 299926-52-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In various solvent(s) at 70℃; for 24h;

Reference： [1]Albrecht; Blau; Rottele [New Journal of Chemistry, 2000, vol. 24, # 8, p. 619 - 622]

14
[ 36748-99-9 ]
7-[(E)-2-(2,3-Dimethoxy-phenyl)-vinyl]-8-methoxy-quinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 98 percent / CuI; (Ph₃P)2PdCl₂ / various solvent(s) / 24 h / 70 °C 2: hydrogen / Pd/C / methanol / 1.08 h

Reference： [1]Albrecht; Blau; Rottele [New Journal of Chemistry, 2000, vol. 24, # 8, p. 619 - 622]

15
[ 36748-99-9 ]
[ 299926-53-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 98 percent / CuI; (Ph₃P)2PdCl₂ / various solvent(s) / 24 h / 70 °C 2: 9 percent / hydrogen / Pd/C / methanol / 1.08 h

Reference： [1]Albrecht; Blau; Rottele [New Journal of Chemistry, 2000, vol. 24, # 8, p. 619 - 622]

16
[ 36748-99-9 ]
[ 299926-55-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 98 percent / CuI; (Ph₃P)2PdCl₂ / various solvent(s) / 24 h / 70 °C 2: 9 percent / hydrogen / Pd/C / methanol / 1.08 h 3: 100 percent / HBr; water / 2 h / Heating

Reference： [1]Albrecht; Blau; Rottele [New Journal of Chemistry, 2000, vol. 24, # 8, p. 619 - 622]

17
[ 36748-99-9 ]
1-(2,3-dimethoxyphenyl)-2-(8-methoxy-1,2,3,4-tetrahydroquinolin-7-yl)ethane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 98 percent / CuI; (Ph₃P)2PdCl₂ / various solvent(s) / 24 h / 70 °C 2: hydrogen / Pd/C / methanol / 1.08 h
	Multi-step reaction with 2 steps 1: 98 percent / CuI; (Ph₃P)2PdCl₂ / various solvent(s) / 24 h / 70 °C 2: 100 percent / hydrogen / Pd/C / methanol / 15 h

Reference： [1]Albrecht; Blau; Rottele [New Journal of Chemistry, 2000, vol. 24, # 8, p. 619 - 622]
[2]Albrecht; Blau; Rottele [New Journal of Chemistry, 2000, vol. 24, # 8, p. 619 - 622]

18
[ 36748-99-9 ]
[ 239-13-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 76 percent / potassium carbonate / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / ethanol; toluene / 72 h / Heating 2: 70 percent / 20percent sulfuric acid / 6 h / Heating 3: 76 percent / pyridinium chloride / 0.33 h / Heating

Reference： [1]Trecourt, Francois; Mallet, Marc; Mongin, Florence; Queguiner, Guy [Tetrahedron, 1995, vol. 51, # 43, p. 11743 - 11750]

19
[ 36748-99-9 ]
[ 102852-60-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 45 percent / potassium carbonate / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / ethanol; toluene / 72 h / Heating 2: 79 percent / 20percent sulfuric acid / 6 h / Heating 3: 65 percent / pyridinium chloride / 0.33 h / Heating

Reference： [1]Trecourt, Francois; Mallet, Marc; Mongin, Florence; Queguiner, Guy [Tetrahedron, 1995, vol. 51, # 43, p. 11743 - 11750]

20
[ 36748-99-9 ]
[ 172795-88-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 76 percent / potassium carbonate / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / ethanol; toluene / 72 h / Heating 2: 70 percent / 20percent sulfuric acid / 6 h / Heating

Reference： [1]Trecourt, Francois; Mallet, Marc; Mongin, Florence; Queguiner, Guy [Tetrahedron, 1995, vol. 51, # 43, p. 11743 - 11750]

21
[ 36748-99-9 ]
11-methoxy-6H-pyrido<3,2-b>carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 76 percent / potassium carbonate / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / ethanol; toluene / 72 h / Heating 2: 70 percent / 20percent sulfuric acid / 6 h / Heating 3: 1.) conc. sulfuric acid, sodium nitrite; 2.) sodium azide / 1.) water, 45 min; 2.) water, 40 min 4: 69 percent / various solvent(s) / 2 h / 170 °C

Reference： [1]Trecourt, Francois; Mallet, Marc; Mongin, Florence; Queguiner, Guy [Tetrahedron, 1995, vol. 51, # 43, p. 11743 - 11750]

22
[ 36748-99-9 ]
[ 172795-89-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 76 percent / potassium carbonate / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / ethanol; toluene / 72 h / Heating 2: 70 percent / 20percent sulfuric acid / 6 h / Heating 3: 1.) conc. sulfuric acid, sodium nitrite; 2.) sodium azide / 1.) water, 45 min; 2.) water, 40 min

Reference： [1]Trecourt, Francois; Mallet, Marc; Mongin, Florence; Queguiner, Guy [Tetrahedron, 1995, vol. 51, # 43, p. 11743 - 11750]

23
[ 36748-99-9 ]
[ 172795-97-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 45 percent / potassium carbonate / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / ethanol; toluene / 72 h / Heating 2: 79 percent / 20percent sulfuric acid / 6 h / Heating

Reference： [1]Trecourt, Francois; Mallet, Marc; Mongin, Florence; Queguiner, Guy [Tetrahedron, 1995, vol. 51, # 43, p. 11743 - 11750]

24
[ 36748-99-9 ]
9,11-dimethoxy-6H-pyrido<3,2-b>carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 45 percent / potassium carbonate / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / ethanol; toluene / 72 h / Heating 2: 79 percent / 20percent sulfuric acid / 6 h / Heating 3: 1.) conc. sulfuric acid, sodium nitrite; 2.) sodium azide / 1.) water, 45 min; 2.) water, 40 min 4: 52 percent / various solvent(s) / 2 h / 170 °C

Reference： [1]Trecourt, Francois; Mallet, Marc; Mongin, Florence; Queguiner, Guy [Tetrahedron, 1995, vol. 51, # 43, p. 11743 - 11750]

25
[ 36748-99-9 ]
[ 172795-98-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 45 percent / potassium carbonate / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / ethanol; toluene / 72 h / Heating 2: 79 percent / 20percent sulfuric acid / 6 h / Heating 3: 1.) conc. sulfuric acid, sodium nitrite; 2.) sodium azide / 1.) water, 45 min; 2.) water, 40 min

Reference： [1]Trecourt, Francois; Mallet, Marc; Mongin, Florence; Queguiner, Guy [Tetrahedron, 1995, vol. 51, # 43, p. 11743 - 11750]

26
[ 36748-99-9 ]
[ 1426050-64-7 ]
(+)-2-(4-ethyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)-2-(2-fluoro-4-(8-methoxyquinolin-7-yl)phenyl)acetamide [ No CAS ]
(-)-2-(4-ethyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)-2-(2-fluoro-4-(8-methoxyquinolin-7-yl)phenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 26% 2: 28%	Stage #1: 2-(4-bromo-2-fluorophenyl)-2-(4-ethyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)acetamide With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; bis(pinacol)diborane In 1,4-dioxane at 90℃; Stage #2: 7-bromo-8-(methyloxy)quinoline With potassium carbonate In 1,4-dioxane; water at 90℃; for 1h;	54.b; 55.b b) (+)-2-(4-ethyl-3-oxo-l-oxa-4,9-diazaspiro[5.5]undecan-9-yl)-2-(2-fluoro-4-(8- fluoroquinolin-7-yl)phenyl)acetamide General procedure: A 20 mL reaction vial equipped with a stirbar was charged with 2-(4-bromo-2- fluorophenyl)-2-(4-ethyl-3-oxo-l-oxa-4,9-diazaspiro[5.5]undecan-9-yl)acetamide (0.150 g, 0.350 mmol), bis(pinacolato)diboron (0.205 g, 0.806 mmol), PdCl2(dppf)-CH2Cl2 adduct (0.020 g, 0.025 mmol), and potassium acetate (0.076 g, 0.770 mmol). The solids were diluted with 1,4-dioxane (3.12 mL) and the reaction mixture was warmed to 90 °C with stirring overnight. The reaction mixture was then treated with PdCl2(dppf)-CH2Cl2 adduct (0.020 g, 0.025 mmol), 2M aq potassium carbonate (0.385 mL, 0.770 mmol), and 7-bromo- 8-fluoroquinoline (0.091 g, 0.403 mmol), and the resulting reaction mixture was stirred at 90 °C for 1 h. The mixture was then diluted with 20 mL dichloromethane and filtered through a stacked pad of sodium sulfate over celite. The filtrate was concentrated to a residue, which was purified by silica gel flash chromatography (0.5-10% methanol: ethyl acetate). Fractions containing the desired material were pooled and concentrated to a hard lacquer and the product was resolved by chiral preparative HPLC (Chromegachiral CC4, 100% methanol) to afford the title compound in >99% ee as an off white solid (42 mg, 0.081 mmol, 23% yield). MS(ES)+ m/e 495.4 [M+H]+. aD = +40 deg (c = 0.06, methanol). Example 53 (-)-2-(4-ethyl-3-oxo-l-oxa-4,9-diazaspiro[5.5]undecan-9-yl)-2-(2-fluoro-4-(8- fluoroquinolin-7-yl)phenyl)acetamide a) From Example 52b, the title product was isolated in >99% ee using chiral HPLC (Chromegachiral CC4, methanol) (42 mg, 0.081 mmol, 23% yield). MS(ES)+ m/e 495.3 [M+H]+. aD = -39 deg (c = 0.06, methanol).

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2013/28447, 2013, A1 Location in patent: Page/Page column 110

27
[ 36748-99-9 ]
[ 1429790-77-1 ]
(+)-4-cyclopropyl-9-({2,6-difluoro-4-[8-(methyloxy)-7-quinolinyl]phenyl}methyl)-1-oxa-4,9-diazaspiro[5.5]undecane-3,8-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate In 1,4-dioxane at 130℃; for 0.416667h; Microwave irradiation;	14.b (+)-4-cyclopropyl-9-({2,6-difluoro-4-[8-(methyloxy)-7-quinolinyl]phenyl}methyl )-1-oxa-4,9-diazaspiro[5.5]undecane-3,8-dione General procedure: A 5 mL microwave vial equipped with a stirbar was charged with 7-bromo-3-chloroquinoline (152 mg, 0.629 mmol) and PdCI2(dppf)-CH2CI2 adduct (29.9 mg, 0.037 mmol). The solids were taken up in 1 ,4-dioxane (0.546 mL) and treated with a 0.338M 1 ,4-dioxane solution of 4-cyclopropyl-9-(2,6-difluoro-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecane-3,8-dione (1.55 mL, 0.524 mmol). The mixture was treated with 2M aq potassium carbonate (0.524 mL, 1.048mmol). The vial was sealed and the mixture subjected to microwave irradiation at130 °Cfor2S mm on very high absorption setting (Biotage Initiator 60). The mixture was then cooled to room temperature and partitioned between 15 mL each of chloroform and saturated aq sodium bicarbonate. The mixture was separated, the organic layer isolated, and the aqueous layer re-extracted with an additional 15 mL chloroform. The organicswere then pooled, dried over sodium sulfate, filtered, and concentrated to a residue. The residue was purified by flash chromatography (0.3-5.5% methanol:dichloromethane). Fractions containing the desired material were pooled and concentrated to a residue which was then resolved by chiral HPLC (Chiralpak AS-H, 95:5 acetonitrile:methanol) to afford title compound in 100% ee as a white solid (58 mg, 0.112 mmol, 21% yield). Following the procedure described in Example 7c with 7-bromo-8- (methyloxy)quinoline afforded the title product in 100% ee (25% yield). MS(ES)+ m/e 508.1 [M+H]+. αD = +9 deg (c = 0.015, 95:5 acetonitrile:methanol).

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2013/52716, 2013, A1 Location in patent: Page/Page column 49; 50; 53

28
[ 36748-99-9 ]
[ 1534373-36-8 ]
[ 73183-34-3 ]
[ 1534371-30-6 ]

Yield	Reaction Conditions	Operation in experiment
56%	Stage #1: 9-((5-bromo-3-fluoropyridin-2-yl)methyl)-4-cyclopropyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one; bis(pinacol)diborane With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate In 1,4-dioxane at 100℃; for 1h; Sealed tube; Microwave irradiation; Stage #2: 7-bromo-8-(methyloxy)quinoline With potassium carbonate In 1,4-dioxane; water at 100℃; for 17h; Sealed tube; Microwave irradiation;	17.a Example 17 4-cyclopropyl-9-((3-fluoro-5-(8-methoxyquinolin-7-yl)pyridin-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-3-one a) In a microwave vial, a mixture of 9-((5-bromo-3-fluoropyridin-2-yl)methyl)-4- cyclopropyl-l-oxa-4,9-diazaspiro[5.5]undecan-3-one (113 mg, 0.284 mmol)(see Example 45b), bis(pinacolato)diboron (79 mg, 0.312 mmol), potassium acetate (84 mg, 0.851 mmol) and l, -bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (12 mg, 0.015 mmol) in 1,4-dioxane (2 mL) was stirred at 100 °C for 1 h. The reaction was cooled to room temperature. 7-bromo-8-methoxyquinoline (68 mg, 0.286 mmol) and 2M aq. potassium carbonate solution (1 mL, 2.000 mmol) were added and the reaction was stirred at 100 °C for 17 h. The reaction was cooled to room temperature and two layers formed. The organic layer was removed from the reaction vial via pipette transfer, placed in an erlenmeyer flask, dried over magnesium sulfate, and concentrated in vacuo. Purification by silica gel chromatography (0-10% methanol/ethyl acetate) followed by purification by reverse phase HPLC (20-60% acetonitrile /water + 0.1% NH4OH) provided the title product as a light brown solid (75 mg, 56%). MS(ES)+ m/e 477.3 [M+H]+.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/8223, 2014, A2 Location in patent: Page/Page column 70-71

29
[ 36748-99-9 ]
[ 1534373-21-1 ]
[ 1534371-24-8 ]

Yield	Reaction Conditions	Operation in experiment
62%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate In 1,4-dioxane; water at 100℃; for 1h; Sealed tube; Inert atmosphere; Microwave irradiation;	15.b b) 4-cyclopropyl-9-(2,6-difluoro-4-(8-methoxyquinolin-7-yl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-3-one In a sealed microwave vial, a mixture of 4-cyclopropyl-9-(2,6-difluoro-4-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)benzyl)-l-oxa-4,9-diazaspiro[5.5]undecan-3-one (152 mg, 0.329 mmol), 7-bromo-8-methoxyquinoline (78 mg, 0.329 mmol), Ι,Γ- bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (13.42 mg, 0.016 mmol) and 2M aqueous potassium carbonate solution (1 mL, 2 mmol) in 1,4- dioxane (3 mL) was stirred at 100 °C for 1 h. The reaction was cooled to room temperature to form two layers and was diluted with ethyl acetate (5 mL). The organic layer was removed by pipette and placed in a flask, dried over magnesium sulfate, and concentrated in vacuo to give a yellow residue. Purification by silica gel chromatography (0-5% methanol/ethyl acetate) provided the title product as a solid (101 mg, 62%). MS(ES)+ m/e 494.2 [M+H]+.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/8223, 2014, A2 Location in patent: Page/Page column 68

30
[ 36748-99-9 ]
tert-butyl 4-cyano-4-[[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl]piperidine-1-carboxylate [ No CAS ]
t-butyl 4-cyano-4-[[4-(8-methoxy-7-quinolyl)phenyl]methyl]piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With palladium diacetate; sodium carbonate; triphenylphosphine In 1,4-dioxane; water; N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere;	91.3 Step 3. t-Butyl 4-cyano-4-[[4-(8-methoxy-7- quinolyl)phenyl]methyl]piperidine-1-carboxylate Step 3. t-Butyl 4-cyano-4-[[4-(8-methoxy-7- quinolyl)phenyl]methyl]piperidine-1-carboxylate [00695] Palladium acetate (31.6 mg, 0.141 mmol) and triphenylphosphine (148 mg, 0.563 mmol) in 1,4-dioxane (7 mL) were stirred for 15 min under an atmosphere of nitrogen. tert-butyl 4-cyano-4-[[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)phenyl]methyl]piperidine-1-carboxylate (1.2 g, 2.8 mmol), 7-bromo-8- methoxyquinoline (1.01 g, 4.22 mmol), DMF (10 mL) and 1 M of sodium carbonate in H2O (11.2 mL, 11.2 mmol) were added, purged under an atmosphere of nitrogen and then the contents of the flask were heated at 80 °C for 2 h. The reaction mixture was then cooled to room temperature, diluted with EtOAc (100mL), was washed with 1N Na2CO3 (50 mL), brine (50 mL) then dried (Na2SO4). The organics were evaporated in vacuo. The crude product was purified by silica gel (10-50% EtOAc/hexanes) to give the desired tert- butyl 4-cyano-4-[[4-(8-methoxy-7-quinolyl)phenyl]methyl]piperidine-1-carboxylate as an yellow foam (1.4 g, 92%); LCMS m/z = 458 (M + 1); 1H NMR (CDCl3) δ: 8.99 (dd, J=4.14, 1.63 Hz, 1 H), 8.18 (dd, J=8.41, 1.63 Hz, 1 H), 7.67 - 7.73 (m, 2 H), 7.62 - 7.66 (m, 1 H), 7.53 - 7.60 (m, 1 H), 7.36 - 7.46 (m, 3 H), 4.12 (d, J=7.28 Hz, 2 H), 3.89 (s, 3 H), 3.03 (br. s., 2 H), 2.93 - 2.97 (m, 2 H), 1.93 (s, 2 H), 1.54 - 1.60 (m, 2 H), 1.46 (s, 9 H).

Reference： [1]Current Patent Assignee: 89BIO LTD - WO2016/205590, 2016, A1 Location in patent: Paragraph 00695

31
[ 36748-99-9 ]
ethyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4H-spiro[benzo[d][1,3]dioxine-2,4’-piperidine]-1’-carboxylate [ No CAS ]
ethyl 6-(8-methoxy-7-quinolyl)spiro[4H-1,3-benzodioxine-2,4’-piperidine]-1’-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With palladium diacetate; sodium carbonate; triphenylphosphine In 1,4-dioxane; water; N,N-dimethyl-formamide at 85℃;	176 Example 176. Ethyl 6-(8-methoxy-7-quinolyl)spiro[ 4H-1,3-benzodioxine-2,4'-piperidine]-1 'carboxylate A solution of ethyl 6-( 4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)spiro[ 4H-1,3-benzodioxine-2,4'-piperidine]-1'-carboxylate (0.78 g, 1.9 mmol), 7-bromo-8-methoxy-quinoline (0.45 g, 1.9mmol), palladium(II) acetate (0.024 g, 0.11 mmol), triphenylphosphine (0.10 g, 0.38 mmol), 1,4-dioxane (30 mL), and DMF (50 mL) was added aq. Na2C03 (0.5 M) (6.0 mL, 3.0 mmol). Themixture was vacuum degassed then heated at 85 oc overnight. The mixture was treated withwater (120 mL) then cooled toRT and extracted with EtOAc (3X70 mL). The organic extractwas washed with a mixture of water: brine (9: 1, 100 mL) then with brine (1 00 mL ), dried overNa2S04, filtered and concentrated in vacuo. The residue was dried overnight under vacuum thenthe residue was dissolved in DCM, applied to a silica gel loading cartridge (25 g) and purified onsilica gel (40 g, 0-40% EtOAc:hexanes) to afford ethyl6-(8-methoxy-7-quinolyl)spiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-carboxylate (0.637 g, 1.47 mmol, 78%) as an off-white foamAnalysis: LCMS 435 (M + 1); 1H NMR (400 MHz, DMSO-d6) 8: 8.94 (dd, J = 4.3, 1.8 Hz, 1H),8.39 (dd, J= 8.4, 1.6 Hz, 1H), 7.77 (d, J= 8.8 Hz, 1H), 7.58 (d, J= 8.5 Hz, 1H), 7.55 (dd, J=8.3, 4.0 Hz, 1H), 7.48 (dd, J= 8.5, 2.3 Hz, 1H), 7.37 (d, J= 2.0 Hz, 1H), 6.97 (d, J= 8.3 Hz,1H), 4.95 (s, 2H), 4.06 (q, J= 7.0 Hz, 2H), 3.93 (s, 3H), 3.59-3.43 (m, 4H), 1.93-1.82 (m, 4H),1.20 (t, J = 7.2 Hz, 3H).

Reference： [1]Current Patent Assignee: 89BIO LTD - WO2018/112204, 2018, A1 Location in patent: Paragraph 00314

32
[ 36748-99-9 ]
tert-butyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[chromane-2,4’-piperidine]-1’-carboxylate [ No CAS ]
tert-butyl 6-(8-methoxy-7-quinolyl)spiro[chromane-2,4’-piperidine]-1‘-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; sodium carbonate; triphenylphosphine In 1,4-dioxane; water; N,N-dimethyl-formamide at 85℃;	175.1 Step 1. tert-Butyl 6-(8-methoxy-7-quinolyl)spiro[ chromane-2,4'-piperidine]-1 '-carboxylate. Asolution of tert-butyl 6-( 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[ chromane-2,4'piperidine]-1'-carboxylate (0.90 g, 2.1 mmol), 7-bromo-8-methoxy-quinoline (0.50 g, 2.1 mmol),palladium(II) acetate (0.024 g, 0.11 mmol), triphenylphosphine (0.11 g, 0.42 mmol), 1,4-dioxane(30 mL), and DMF (50 mL) was added aq. Na2C03 (0.5 M) (8.0 mL, 4.0 mmol). The mixturewas vacuum degassed then heated at 85 oc overnight. The mixture was treated with water (120mL) then cooled toRT and extracted with EtOAc (3 x 70 mL). The organic extract was washedwith a mixture ofwater:brine (9:1, 100 mL) then with brine (100 mL), dried overNa2S04,filtered and concentrated in vacuo. The residue was dried overnight under vacuum then theresidue was dissolved in DCM, applied to a silica gel loading cartridge (25 g) and purified onsilica gel (40 g, 0-40% ethyl acetate:hexane) to afford tert-butyl 6-(8-methoxy-7-quinolyl)spiro[chromane-2,4'-piperidine]-1'-carboxylate as a white solid. Analysis: LCMS m/z 461 (M +1); 1H NMR (400 MHz, DMSO-d6) 8: 8.94 (dd, J = 4.3, 1.8 Hz, 1H), 8.38 (dd, J = 8.4, 1.6 Hz,1H), 7.75 (d, J= 8.5 Hz, 1H), 7.58 (d, J= 8.5 Hz, 1H), 7.56-7.52 (m, 1H), 7.42-7.36 (m, 2H),6.90 (d,J= 8.3 Hz, 1H), 3.93 (s, 3H), 3.78-3.68 (m, 2H), 3.29-3.11 (m, 2H), 2.82 (t,J= 6.7 Hz,2H), 1.85 (t, J= 6.8 Hz, 2H), 1.79-1.70 (m, 2H), 1.62-1.52 (m, 2H), 1.42 (s, 9H).

Reference： [1]Current Patent Assignee: 89BIO LTD - WO2018/112204, 2018, A1 Location in patent: Paragraph 00314

33
[ 36748-99-9 ]
tert-butyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-carboxylate [ No CAS ]
tert-butyl 6-(8-methoxy-7-quinolyl)spiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With palladium diacetate; sodium carbonate; triphenylphosphine In 1,4-dioxane; water; N,N-dimethyl-formamide at 85℃;	174.1 Step 1. tert-Butyl 6-(8-methoxy-7-quinolyl)spiro[4H-1,3-benzodioxine-2,4'-piperidine]-1 'carboxylate. tert-Butyl 6-( 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[ 4H-1,3-benzodioxine-2,4'-piperidine]-1'-carboxylate (0.80 g, 1.9 mmol), 7-bromo-8-methoxy-quinoline (0.45g, 1.9 mmol), palladium(II) acetate (0.024 g, 0.11 mmol) and triphenylphosphine (0.10 g, 0.38mmol) in 1,4-dioxane (30 mL), DMF (50 mL) was added aq. Na2C03 (0.5 M) (6.0 mL, 3.0mmol). The mixture was vacuum degassed then heated at85 oc overnight. The mixture was diluted with EtOAc (200 mL) and water (100 mL) andextracted. The aqueous extract was washed with EtOAc (50 mL) and the combined organics were dried over Na2S04, filtered and concentrated. The residue was dissolved in DCM, appliedto a silica gel loading cartridge (5 g) and purified on silica gel (80 g, 0-40% EtOAc:hexanes) toafford tert-butyl 6-(8-methoxy-7-quinolyl)spiro[ 4H-1 ,3-benzodioxine-2,4'-piperidine ]-1 'carboxylate(0.38 g, 0.82 mmol, 43% Yield). LCMS m/z = 463.

Reference： [1]Current Patent Assignee: 89BIO LTD - WO2018/112204, 2018, A1 Location in patent: Paragraph 00314

34
[ 36748-99-9 ]
tert-butyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[4H-1,3-benzodioxine-2,4'-piperidine]-1'-carboxylate [ No CAS ]
(x)C₂HF₃O₂*C₂₂H₂₂N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium carbonate; palladium diacetate; triphenylphosphine / N,N-dimethyl-formamide; 1,4-dioxane; water / 85 °C 2: dichloromethane / 24 h / 20 °C

Reference： [1]Current Patent Assignee: 89BIO LTD - WO2018/112204, 2018, A1

35
[ 36748-99-9 ]
[ 538-51-2 ]
C₂₃H₂₀N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 7-bromo-8-(methyloxy)quinoline With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: benzylidene phenylamine In tetrahydrofuran at 20℃; for 10h;

Reference： [1]Pobbati, Ajaybabu V.; Mejuch, Tom; Chakraborty, Sayan; Karatas, Hacer; Bharath, Sakshibeedu R.; Guéret, Stéphanie M.; Goy, Pierre-Alexis; Hahne, Gernot; Pahl, Axel; Sievers, Sonja; Guccione, Ernesto; Song, Haiwei; Waldmann, Herbert; Hong, Wanjin [ACS Chemical Biology, 2019, vol. 14, # 12, p. 2909 - 2921]

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Physical hazards
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
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H221	Flammable gas
H222	Extremely flammable aerosol
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H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
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H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
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Health hazards
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H300	Fatal if swallowed
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H302	Harmful if swallowed
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H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
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Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 36748-99-9 ]

Application In Synthesis of [ 36748-99-9 ]

[ 36748-99-9 ] Synthesis Path-Downstream 1~35

Related Functional Groups of [ 36748-99-9 ]

Bromides

Ethers

Related Parent Nucleus of [ 36748-99-9 ]

Quinolines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 36748-99-9 ]

Related Parent Nucleus of
[ 36748-99-9 ]