[ CAS No. 2540-30-9 ] {[proInfo.proName]}

Name: 2540-30-9|4-Methyl-1-phenylquinolin-2(1H)-one|95%
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Quality Control of [ 2540-30-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 2540-30-9 ]

Product Details of [ 2540-30-9 ]

CAS No. :	2540-30-9	MDL No. :	MFCD00024050
Formula :	C₁₆H₁₃NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ILKUVYJZEPVFHW-UHFFFAOYSA-N
M.W :	235.28	Pubchem ID :	269183
Synonyms :

Calculated chemistry of [ 2540-30-9 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	16
Fraction Csp3 :	0.06
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	74.51
TPSA :	22.0 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) :	-5.61 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.69
Log Po/w (XLOGP3) :	2.99
Log Po/w (WLOGP) :	3.3
Log Po/w (MLOGP) :	3.6
Log Po/w (SILICOS-IT) :	3.6
Consensus Log Po/w :	3.24

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.77
Solubility :	0.0396 mg/ml ; 0.000168 mol/l
Class :	Soluble
Log S (Ali) :	-3.12
Solubility :	0.18 mg/ml ; 0.000766 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.69
Solubility :	0.000477 mg/ml ; 0.00000203 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.94

Safety of [ 2540-30-9 ]

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

Application In Synthesis of [ 2540-30-9 ]

* 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 [ 2540-30-9 ]
Downstream synthetic route of [ 2540-30-9 ]

[ 2540-30-9 ] Synthesis Path-Upstream 1~10

1
[ 21298-82-8 ]
[ 2540-30-9 ]

Reference： [1] Organic Letters, 2018, vol. 20, # 1, p. 240 - 243

2
[ 607-66-9 ]
[ 66003-76-7 ]
[ 2540-30-9 ]

Reference： [1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 23, p. 4956 - 4961

3
[ 2540-31-0 ]
[ 2540-30-9 ]

Reference： [1] Zhurnal Obshchei Khimii, 1937, vol. 7, p. 2365,2369,2371[2] Chem. Zentralbl., 1938, vol. 109, # II, p. 844
[3] Chemische Berichte, 1936, vol. 69, p. 2023,2025
[4] Zhurnal Obshchei Khimii, 1937, vol. 7, p. 2365,2369,2371[5] Chem. Zentralbl., 1938, vol. 109, # II, p. 844
[6] Chemische Berichte, 1936, vol. 69, p. 2023,2025
[7] Patent: EP1362894, 2003, A2,

4
[ 3724-65-0 ]
[ 122-39-4 ]
[ 2540-30-9 ]

Reference： [1] Chemistry - A European Journal, 2015, vol. 21, # 23, p. 8360 - 8364

5
[ 607-66-9 ]
[ 591-50-4 ]
[ 12775-96-1 ]
[ 2540-30-9 ]

Reference： [1] Patent: US5545535, 1996, A,
[2] Patent: US5658751, 1997, A,

6
[ 607-66-9 ]
[ 591-50-4 ]
[ 2540-30-9 ]

Reference： [1] Patent: US5436134, 1995, A,

7
[ 519-87-9 ]
[ 2540-30-9 ]

8
[ 857619-99-9 ]
[ 2540-30-9 ]

Reference： [1] Zhurnal Obshchei Khimii, 1937, vol. 7, p. 2365,2369,2371[2] Chem. Zentralbl., 1938, vol. 109, # II, p. 844
[3] Chemische Berichte, 1936, vol. 69, p. 2023,2025

9
[ 7664-93-9 ]
[ 2540-31-0 ]
[ 2540-30-9 ]

Reference： [1] Zhurnal Obshchei Khimii, 1937, vol. 7, p. 2365,2369,2371[2] Chem. Zentralbl., 1938, vol. 109, # II, p. 844
[3] Chemische Berichte, 1936, vol. 69, p. 2023,2025

10
[ 7664-93-9 ]
[ 857619-99-9 ]
[ 2540-30-9 ]

Reference： [1] Zhurnal Obshchei Khimii, 1937, vol. 7, p. 2365,2369,2371[2] Chem. Zentralbl., 1938, vol. 109, # II, p. 844
[3] Chemische Berichte, 1936, vol. 69, p. 2023,2025

[ 2540-30-9 ] Synthesis Path-Downstream 1~40

1
[ 2540-31-0 ]
[ 2540-30-9 ]

Yield	Reaction Conditions	Operation in experiment
	In sulfuric acid; ethyl acetate;	(10-1) Synthesis of 4-methyl-1-phenyl-1,2-dihydroquinolin-2-one In a volume of 150 mL of concentrated sulfuric acid was added portionwise with 60 g of N,N-diphenylacetoacetamide at 5-10C. After substantially complete dissolution was attained, the solution was left overnight at room temperature. After completion of the reaction, the reaction mixture was poured into ice water, added with 200 mL of ethyl acetate and stirred, and crystals deposited. The crystals were collected by filtration and dried to obtain the desired substance.

Reference： [1]Zhurnal Obshchei Khimii,1937,vol. 7,p. 2365,2369,2371
Chemisches Zentralblatt,1938,vol. 109,p. 844
[2]Zhurnal Obshchei Khimii,1937,vol. 7,p. 2365,2369,2371
Chemisches Zentralblatt,1938,vol. 109,p. 844
[3]Patent: EP1362894,2003,A2

2
[ 857619-99-9 ]
[ 2540-30-9 ]

Reference： [1]Zhurnal Obshchei Khimii,1937,vol. 7,p. 2365,2369,2371
Chemisches Zentralblatt,1938,vol. 109,p. 844

4
[ 7664-93-9 ]
[ 2540-31-0 ]
[ 2540-30-9 ]

Reference： [1]Zhurnal Obshchei Khimii,1937,vol. 7,p. 2365,2369,2371
Chemisches Zentralblatt,1938,vol. 109,p. 844

5
[ 7664-93-9 ]
[ 857619-99-9 ]
[ 2540-30-9 ]

Reference： [1]Zhurnal Obshchei Khimii,1937,vol. 7,p. 2365,2369,2371
Chemisches Zentralblatt,1938,vol. 109,p. 844

6
[ 519-87-9 ]
[ 2540-30-9 ]

7
4-methyl-2-(methylthio)[1,3]oxazolo[4,5-b]pyridin-4-ium tosylate [ No CAS ]
[ 2540-30-9 ]
[ 305801-88-1 ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of 6 g of Compound 1, 3 g of <strong>[2540-30-9]4-methyl-1-phenyl-2-quinolone</strong>, 8.9 mL diisopropylethylamine, and 1.2 mL of trimethylsilyl trifluoromethanesulfonate is heated at reflux in 100 mL of CH2Cl2 for 1 hour. The reaction mixture is cooled on ice and 100 mL of water is added slowly with stirring. The layers are separated and the aqueous layer is extracted with chloroform. The combined organic layers are washed with brine and dried over Na2SO4. The crude 4-oxazolopyridinylmethylidenequinolone thus obtained is heated at reflux for 3 hours with 5.8 mL of phosphorus oxychloride and 100 mL of dichloroethane. The reaction mixture is cooled to room temperature, 100 mL of water is added and after 30 min, the crude product is recovered by filtration. The crude product is purified by chromatography on a silica gel column to yield Compound 29. A mixture of 0.1 g of Compound 29, 10 mL of dichloroethane and 0.27 mL of diethylamine is heated at 60 C. in a sealed tube for 2.5 hours. The volatile components are evaporated and the crude residue is purified by chromatography on a silica gel column to yield Compound 30.

Reference： [1]Patent: US6664047,2003,B1 .Location in patent: Page column 49

8
[ 607-66-9 ]
[ 591-50-4 ]
[ 2540-30-9 ]

Yield	Reaction Conditions	Operation in experiment
		Example 1 Preparation of 1,2-dihydro-4-methyl-1-phenyl-2-quinolone (1) The following compound is prepared: STR7 The starting 1,2-dihydro-4-methyl- 1 -phenyl-2-quinolone (1) is prepared either by an Ullmann coupling according to a literature procedure (Wawzonek et al., supra.) or via the reaction of the corresponding diarylamine with dikctene followed by acid cyclization (Elderfield, supra). Thus 10.0 g (62.9 mmoles) of 2-hydroxy-4-methylquinoline is heated at reflux with 24.0 g (377 mmolcs) of copper powder, 8.68 g (62.9 mmoles) of potassium carbonate and 19.2 g (94 mmoles) of iodobenzene for 48 hours. The reaction is cooled to room temperature, partitioned between water and ethyl acetate, filtered, and the organic layer is dried over magnesium sulfate. The crude product is purified on a silica gel column, eluding with 1:1 ethyl acetate/hexanes to yield 8.1 g of the desired product.

Reference： [1]Patent: US5436134,1995,A

9
[ 2540-30-9 ]
[ 55514-14-2 ]
2-fluoro-4-[2,3-dihydro-4-methyl-(benzo-1,3-thiazol-2-yl)-methylidene]-1-phenylquinolinium iodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With diethylaminosulfur trifluoride; triethylamine; In dichloromethane; N,N-dimethyl-formamide;	Example 38 Preparation 2-fluoro-4-[2,3-dihydro-4-methyl-(benzo-1,3-thiazol-2-yl) -methylidene]-1-phenylquinolinium iodide (dye 834) Diethylaminosulfur trifluoride (0.26 mL) is added to 0.47 g of <strong>[2540-30-9]1,2-dihydro-<strong>[2540-30-9]4-methyl-1-phenyl-2-quinolone</strong></strong> (example 1) in 5 mL of methylene chloride, and the mixture is heated at 80 C. in a sealed tube for 16 hours. The resulting solution is added to a mixture of 0.74 g of 3-methyl-2-methylthiobenzothiazolium tosylate and 0.28 mL of triethylamine in a mixed solution of 10 mL DMF and 20 mL methylene chloride. After 10 minutes of additional stirring, the reaction is washed with 1 N HCl, with NaCl and subsequently dried over magnesium chloride. The product is isolated by column chromatography on silica gel.

Reference： [1]Patent: US5436134,1995,A

10
[ 2540-30-9 ]
[ 55514-14-2 ]
[ 7789-60-8 ]
2-bromo-4-[2,3-dihydro-3-methyl-(benzo-1,3-thiazol-2-yl)-methylidene ]-1-phenylquinolinium iodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;	Example 8 Preparation of 2-bromo-4-[2,3-dihydro-3-methyl-(benzo-1,3-thiazol-2-yl)-methylidene ]-1-phenylquinolinium iodide (dye 774) The following compound is prepared: STR14 To 0.47 g (2 mmoles) of <strong>[2540-30-9]1,2-dihydro-<strong>[2540-30-9]4-methyl-1-phenyl-2-quinolone</strong></strong> (Example 1) in 8 mL of toluene is added, 0.6 g (2.2 mmoles) of phosphorous tribromide and the solution is heated to reflux for 30 minutes. The mixture is cooled to room temperature, diluted with 20 mL of ethyl acetate and filtered. The solid thus obtained is suspended in 15 mL of methylene chloride and added to a solution of 3-methyl-2-methylthiobenzothiazolium tosylate (0.55 g, 1.5 mmoles) and triethylamine (0.35 mL, 1.8 mmoles) in 8 mL of DMF. The reaction mixture is stirred for 30 minutes and the red solid is separated by filtration. The volatile components of the filtrate are removed under reduced pressure and the residue is purified using a silica gel column, glueing with 3:3:1 ethyl acetate/chloroform/methanol. The restrange band that has a slightly higher Rf than the 2-chloro-4-[2,3-dihydro-3-methyl-(benzo-1,3-thiazol-2-yl) -methylidene] -1-quinolinium iodide (Example 7) is isolated, redissolved in about 1.5 mL of methanol and added to 1.5 g of NaI in 20 mL of water. The product is isolated by filtration as the iodide salt and dried in vacuo.

Reference： [1]Patent: US5436134,1995,A

11
silyl enolate [ No CAS ]
[ 2540-30-9 ]
[ 55514-14-2 ]
[ 61304-90-3 ]

Yield	Reaction Conditions	Operation in experiment
	With trimethylsilyl trifluoromethanesulfonate; triethylamine; lithium diisopropyl amide; trichlorophosphate;N-methyl-acetamide; In methanol; dichloromethane; chloroform; ethyl acetate;	Example 7 Preparation of 2-chloro-4-[2,3 -dihydro-3-methyl-(benzo-1,3-thiazol-2-yl) -methylidene]-1-phenylquinolinium iodide (dye 591) The following compound is prepared: STR13 To 2.8 g (11.9 mmoles) of <strong>[2540-30-9]1,2-dihydro-<strong>[2540-30-9]4-methyl-1-phenyl-2-quinolone</strong></strong> (Example 1) in 20 mL of methylene chloride is added, 1.85 g of phosphorus oxychloride and a catalytic amount of dimethylformamide (Marson, TETRAHEDRON., 48, 3659 (1992)). The resulting mixture is heated to reflux for 24 hours. The reaction mixture is cooled to room temperature and 3.5 g (9.6 mmoles) of N-methyl-2-methylthiobenzothiazolium tosylate (Rye, et al., NUCLEIC ACIDS RES., 20, 2803 (1992)) is added followed by 1.3 mL (9.4 mmoles) of triethylamine. The mixture is stirred for an additional 6 hours. The crude product is purified on silica gel using ethyl acetate:chloroform:methanol, 3:3:1 as eluant. The product is then recrystallized from methanol/chloroform/ethyl acetate. An additional synthetic rotitc to this product utilizes 4-[2,3-dihydro-3-methyl-(benzo-1,3-thiazol-2-yl) -methylidene[-1,2-dihydro-1-phenyl-2-quinolone (4), which in turn is prepared from <strong>[2540-30-9]1,2-dihydro-<strong>[2540-30-9]4-methyl-1-phenyl-2-quinolone</strong></strong> (1) and 3-methyl-2-methylthiobenzothiazolium tosylate. Thus the lithium enolate of the (1) (prepared from treating the quinolone with 2.7 equivalent of lithium diisopropyl amide) or the silyl enolate (from (1) and trimethylsilyl trifluoromethanesulfonate and diisopropylethylamine) is stirred with the benzothiazolium tosylate. The desired intermediate (4) is isolated by column chromatography.

Reference： [1]Patent: US5436134,1995,A

12
[ 607-66-9 ]
[ 591-50-4 ]
[ 12775-96-1 ]
[ 2540-30-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;	Example 1 Preparation of 1,2-dihydro-4-methyl-1-phenyl-2-quinolone (1) The following compound is prepared: STR10 The starting 1,2-dihydro-4-methyl-1-phenyl-2-quinolone (1) is prepared either by an Ullmann coupling according to a literature procedure (e.g. S. Wawzonek and T. V. Truong, J. HETEROCYCLIC CHEM., 25, 381 (1988).) or via the reaction of the corresponding diarylamine with diketene followed by acid cyclization (e.g. R. C. Elderfield, ed., HETEROCYCLIC COMPOUNDS vol. 4, pp. 1-331, 1952). Thus 10.0 g (62.9 mmoles) of 2-hydroxy-4-methylquinoline is heated at reflux with 24.0 g (377 mmoles) of copper powder, 8.68 g (62.9 mmoles) of potassium carbonate and 19.2 g (94 mmoles) of iodobenzene for 48 hours. The reaction is cooled to room temperature, partitioned between water and ethyl acetate, filtered, and the organic layer is dried over magnesium sulfate. The crude product is purified on a silica gel column, eluding with 1:1 ethyl acetate/hexanes to yield 8.1 g of the desired product.
	With potassium carbonate;	Example 1 Preparation of 1,2-dihydro-4-methyl-1-phenyl-2-quinolone (1) The following compound is prepared: STR89 The synthetic precursor (1) is prepared either by an Ullmann coupling according to a literature procedure (Wawzonek, et al., J. HETEROCYCLIC CHEM., 25, 381 (1988)) or via the reaction of the corresponding diarylamine with diketene followed by acid cyclization (Elderfield, HETEROCYCLIC COMPOUNDS, Vol. 4, pp. 1-331, (1952)). Thus 10.0 g (62.9 mmoles) of 2-hydroxy-4-methylquinoline is heated at reflux with 24.0 g (377 mmoles) of copper powder, 8.68 g (62.9 mmoles) of potassium carbonate and 19.2 g (94 mmoles) of iodobenzene for 48 hours. The reaction is cooled to room temperature, partitioned between water and ethyl acetate, filtered, and the organic layer is dried over magnesium sulfate. The crude product is purified on a silica gel column, eluding with 1:1 ethyl acetate/hexanes to yield 8.1 g of the desired product.

Reference： [1]Patent: US5545535,1996,A
[2]Patent: US5658751,1997,A

13
[ 2540-30-9 ]
[ 55514-14-2 ]
2-methoxy-4-[2,3-dihydro-3-methyl-(benzo-1,3-thiazol-2-yl)-methylidene]-1-phenylquinolinium iodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate;N-methyl-acetamide; In methanol; dichloromethane; triethylamine;	Example 4 Preparation of 2-methoxy-4-[2,3-dihydro-3-methyl(benzo-1,3-thiazol-2-yl)-methylidene]-1-phenylquinolinium iodide (dye 628) The following compound is prepared: STR13 To 1.0 g (4.3 mmoles)of <strong>[2540-30-9]1,2-dihydro-<strong>[2540-30-9]4-methyl-1-phenyl-2-quinolone</strong></strong> (Example 1) in about 10 mL of methylene chloride, 2 mL of phosphorous oxychloride is added followed by a catalytic amount of dimethylformamide. After 3 hours under reflux, all the volatile components are removed under reduced pressure. Ten mL of methanol is added to the residue, and the solution is heated for an additional 2 hours. The methanol is removed under reduced pressure, and 10 mL of methylene chloride is added, followed by 1.56 g (4.3 mmoles) of N-methyl-2-methylthiobenzothiazolium tosylate and 1.5 mL of triethylamine (e.g. H. S Rye, et al., NUCLEIC ACIDS RES., 20, 2803 (1992)). The resulting mixture is stirred at room temperature for 3 days. The crude material is purified on a silica gel column by eluding with 5:5:1 ethyl acetate: chloroform: methanol. The same dye is prepared by stirring dye 691 in methanol at room temperature in tile presence of 10 equivalents of triethylamine for about one hour.

Reference： [1]Patent: US5545535,1996,A

14
silyl enolate [ No CAS ]
[ 2540-30-9 ]
4-[2,3-dihydro-3-methyl-(benzo-1,3-thiazol-2-yl)-methylidene]-1-phenyl-1,2-dihydro-2-quinolone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trimethylsilyl trifluoromethanesulfonate; lithium diisopropyl amide;	An additional synthetic route to the product utilizes 4-[2,3-dihydro-3-methyl-(benzo-1,3-thiazol-2-yl)-methylidene]-1,2-dihydro-1-phenyl-2-quinolone (5), which in turn is prepared from <strong>[2540-30-9]1,2-dihydro-<strong>[2540-30-9]4-methyl-1-phenyl-2-quinolone</strong></strong> (1) and 4. Thus the lithium enolate of 1 (prepared from treating the quinolone with 2.7 equivalent of lithium diisopropyl amide) or the silyl enolate of 1 (from (1) and trimethylsilyl trifluoromethanesulfonate and diisopropylethylamine) is stirred with 4.

Reference： [1]Patent: US5658751,1997,A

15
[ 2540-30-9 ]
[ 105-58-8 ]
[ 61298-12-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In methanol; ethanol;	The malonate used as starting material was obtained as follows: A mixture of 1,2-dihydro-4-methyl-2-oxo-1-phenylquinoline (4.7 g.), sodium hydride (4.8 g., 60% w/w dispersion in oil, washed as in Example 1) and diethyl carbonate (50 ml.) was stirred under reflux for 2 hours. Any excess of sodium hydride was then destroyed by addition of methanol to the cooled suspension, and the mixture was then poured into ether (1 l.). The yellow precipitate was collected by filtration, and washed with ether (200 ml.). It was suspended in ethanol (50 ml.), concentrated hydrochloric acid was added to give a pH of 3, and the resultant solution was poured into water (200 ml.). The precipitate was extracted into ether, and the combined extracts were washed with water, dried over magnesium sulphate, and evaporated in vacuo. A sample of the residual solid was recrystallized from a mixture of benzene and cyclohexane to give diethyl 1,2-dihydro-2-oxo-1-phenylquinol-4-ylmalonate, m.p. 101-103 C.
	With hydrogenchloride; In methanol; ethanol;	The malonate used as starting material was obtained as follows: A mixture of 1,2-dihydro-4-methyl-2-oxo-1-phenylquinoline (4.7 g.), sodium hydride (4.8 g., 60% w/w dispersion in oil, washed as in Example 1) and diethyl carbonate (50 ml.) was stirred under reflux for 2 hours. Any excess of sodium hydride was then destroyed by addition of methanol to the cooled suspension, and the mixture was then poured into ether (1 l.). The yellow precipitate was collected by filtration, and washed with ether (200 ml.). It was suspended in ethanol (50 ml.), concentrated hydrochloric acid was added to give a pH of 3, and the resultant solution was poured into water (200 ml.). The precipitate was extracted into ether, and the combined extracts were washed with water, dried over magnesium sulphate, and evaporated in vacuo. A sample of the residual solid was recrystallized from a mixture of benzene and cyclohexane to give diethyl 1,2-dihydro-2-oxo-1-phenylquinol-4-ylmalonate, m.p. 101-103 C.

Reference： [1]Patent: US4066651,1978,A
[2]Patent: US4138490,1979,A

16
4-methyl-2-(methylthio)[1,3]oxazolo[4,5-b]pyridin-4-ium tosylate [ No CAS ]
[ 109-72-8 ]
[ 2540-30-9 ]
[ 305801-74-5 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 0.235 g of <strong>[2540-30-9]4-methyl-1-phenyl-2-quinolone</strong> in 15 mL THF at -78 C., is added 0.6 mL of a 2.5 M solution of 1-butyl lithium in THF. After 1 hr at -78 C., 1 mL of acetic acid is added. The reaction mixture is stirred for 1 hr at room temperature. The volatiles are evaporated and the residue is dissolved in 10 mL CH2Cl2. Compound 1 (0.7 g) and 1 mL triethylamine are added. After 1 hr at room temperature the solvent is evaporated, the crude product is dissolved in 10 mL of methanol and the solution is then added to 2.5 g NaI in 60 mL water. The product, Compound 15, is filtered and further purified by column chromatography on silica gel.

Reference： [1]Patent: US6664047,2003,B1 .Location in patent: Page column 43

17
[ 3724-65-0 ]
[ 122-39-4 ]
[ 2540-30-9 ]

Reference： [1]Chemistry - A European Journal,2015,vol. 21,p. 8360 - 8364

18
[ 2540-30-9 ]
3-methyl-2-methylthiobenzothiazolium tosylate [ No CAS ]
C₂₄H₁₈N₂OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3 g	With trimethylsilyl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0℃;Reflux;	Example 17 Preparation of Compound 57 (0235) (0236) To a mixture of 3-methyl-2-methylthiobenzothiazolium tosylate (5 g, 13.6 mmol), <strong>[2540-30-9]1,2-dihydro-<strong>[2540-30-9]4-methyl-1-phenyl-2-quinolone</strong></strong> (prepared according to U.S. Pat. No. 5,658,751) (3 g, 11.3 mmol) and N,N-diisopropylethylamine (7.8 mL, 45 mmol) in CH2Cl2 (100 mL) at 0 C. was added trimethysilyl trifluoromethanesulfonate (10.3 mL, 57 mmol) dropwise. After the addition was completed, the solution was refluxed for 1 hr and then cooled down to 0 C. Water (110 mL) was added dropwise and the mixture was stirred at 0 C. for 1 hr. The aqueous layer was extracted with CH2Cl2 (2×50 mL) and the combined organic layers was dried with anhydrous Na2SO4. The solvent was removed and the residue was dried to a constant weight (3 g) and used without further purification.

Reference： [1]Patent: US2016/24067,2016,A1 .Location in patent: Paragraph 0235-0236

19
[ 2540-30-9 ]
C₂₅H₁₈F₃N₂O₃S₂⁽¹⁺⁾*CF₃O₃S^(1-) [ No CAS ]

Reference： [1]Patent: US2016/24067,2016,A1

20
[ 2540-30-9 ]
C₃₃H₃₇N₆S⁽¹⁺⁾*C₂F₃O₂^(1-) [ No CAS ]

Reference： [1]Patent: US2016/24067,2016,A1

21
[ 2540-30-9 ]
C₃₂H₃₆N₅S⁽¹⁺⁾*C₂F₃O₂^(1-) [ No CAS ]

Reference： [1]Patent: US2016/24067,2016,A1

22
[ 2540-30-9 ]
C₃₁H₃₅N₆S⁽¹⁺⁾*C₂F₃O₂^(1-) [ No CAS ]

Reference： [1]Patent: US2016/24067,2016,A1

23
[ 2540-30-9 ]
C₃₆H₃₈N₄S⁽²⁺⁾*2Br^(1-) [ No CAS ]

Reference： [1]Patent: US2016/24067,2016,A1

24
[ 109-72-8 ]
[ 2540-30-9 ]
1-(methylthio)-7,8-dihydro-6H-thiazolo[5,4,3-ij]quinolin-9-ium p-toluenesulfonate [ No CAS ]
C₃₀H₂₉N₂S⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.12 g		Example 37 Preparation of Compound 71 (0275) (0276) To a solution of <strong>[2540-30-9]1,2-dihydro-<strong>[2540-30-9]4-methyl-1-phenyl-2-quinolone</strong></strong> (0.2 g, 1 mmol) in THF (15 mL) at -78 C. was added 2.5 M n-butyllithium in hexanes (1.5 mL, 3.75 mmol). The mixture was stirred at -78 C. for one hour and acetic acid (0.4 mL,) was added. The mixture was warmed up slowly to room temperature and kept stirring at room temperature for another 3 hrs. The mixture was evaporated to dryness in vacuo. The residue was re-dissolved in CH2Cl2 (20 mL), followed by the addition of 1-(methylthio)-7,8-dihydro-6H-thiazolo[5,4,3-ij]quinolin-9-ium tosylate (0.394 g, 1 mmol) (prepared according to US patent application No. 20100233710) and triethylamine (0.56 mL). The mixture was stirred at room temperature for 2 hrs and then concentrated to dryness in vacuo. The residue was dissolved in DMF (5 mL) and added dropwise to a solution of NaI (1.7 g) in water (90 mL). The precipitate was collected by suction filtration and dried to a constant weight (0.12 g).

Reference： [1]Patent: US2016/24067,2016,A1 .Location in patent: Paragraph 0275-0276

25
[ 2540-30-9 ]
[ 6274-57-3 ]
1-(methylthio)-7,8-dihydro-6H-thiazolo[5,4,3-ij]quinolin-9-ium p-toluenesulfonate [ No CAS ]
C₃₅H₃₂N₃S⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 39 Preparation of Compound 73 (0279) (0280) To 4?-bromobenzyldiethylamine (0.3 g, 1.23 mmol) in anhydrous THF (10 mL) at -78 C. under N2 was added 2.5 M n-butyllithium in hexanes (0.5 mL, 1.23 mmol) and then followed by the addition of 1,2-dihydro-4-methyl-1-phenyl-2-quinolone (0.3 g, 1.25 mmol) in THF (10 mL). The mixture was stirred at -78 C. for 1 hour and HOAc (0.5 mL) was added. The mixture was stirred at room temperature for another hour and then concentrated to dryness in vacuo. The residue was dissolved in CH2Cl2 (10 mL) and then followed by the addition of 1-(methylthio)-7,8-dihydro-6H-thiazolo[5,4,3-ij]quinolin-9-ium tosylate (0.484 g, 1.23 mmol) and triethylamine (0.56 mL). The mixture was stirred at room temperature for 2 hrs and concentrated to dryness in vacuo. The residue was dissolved in MeOH (5 mL) and then added dropwise to a solution of NaI (2 g) in water (50 mL). The orange precipitate (42 mg) was collected by suction filtration and dried to a constant weight.

Reference： [1]Patent: US2016/24067,2016,A1 .Location in patent: Paragraph 0279-0280

26
[ 2540-30-9 ]
[ 55514-14-2 ]
C₂₄H₁₈ClN₂S⁽¹⁺⁾*Cl^(1-) [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2017,vol. 12,p. 233 - 238

27
[ 2540-30-9 ]
[ 55514-14-2 ]
2-(diethylamino)-4-{((3-methylbenzo[d]thiazol-2(3H)-ylidene)methyl)}-1-phenylquinolin-1-ium chloride [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2017,vol. 12,p. 233 - 238

28
[ 607-66-9 ]
[ 66003-76-7 ]
[ 2540-30-9 ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 4956 - 4961

29
[ 21298-82-8 ]
[ 2540-30-9 ]

Reference： [1]Organic Letters,2018,vol. 20,p. 240 - 243

30
[ 2540-30-9 ]
[ 501-65-5 ]
4-methyl-1-(5,6,7,8-tetraphenylnaphthalen-1-yl)quinolin-2(1H)-one [ No CAS ]
4-methyl-1-(5,6,7,8-tetraphenylnaphthalen-1-yl)quinolin-2(1H)-one [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 6732 - 6736
Angew. Chem.,2019,vol. 131,p. 6804 - 6808,5

31
[ 4329-95-7 ]
[ 2540-30-9 ]
[ 1517-05-1 ]
C₂₆H₂₂N₅OS⁽¹⁺⁾*ClO₄^(1-) [ No CAS ]

Reference： [1]Patent: WO2019/177541,2019,A1 .Location in patent: Page/Page column 9; 21

32
[ 2540-30-9 ]
C₁₇H₁₆NS⁽¹⁺⁾*Cl^(1-) [ No CAS ]