[ CAS No. 550998-53-3 ] {[proInfo.proName]}

Name: 550998-53-3|Methyl 7-bromobenzo[b]thiophene-2-carboxylate|98%
Brand: Ambeed
SKU: A168057
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Quality Control of [ 550998-53-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 550998-53-3 ]

Product Details of [ 550998-53-3 ]

CAS No. :	550998-53-3	MDL No. :	MFCD09027095
Formula :	C₁₀H₇BrO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JEHZRZXWHVICJQ-UHFFFAOYSA-N
M.W :	271.13	Pubchem ID :	18526159
Synonyms :

Calculated chemistry of [ 550998-53-3 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.1
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	60.8
TPSA :	54.54 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.24 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.66
Log Po/w (XLOGP3) :	3.82
Log Po/w (WLOGP) :	3.45
Log Po/w (MLOGP) :	2.96
Log Po/w (SILICOS-IT) :	4.14
Consensus Log Po/w :	3.41

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.27
Solubility :	0.0145 mg/ml ; 0.0000535 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.66
Solubility :	0.00592 mg/ml ; 0.0000218 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-4.27
Solubility :	0.0145 mg/ml ; 0.0000536 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.33

Safety of [ 550998-53-3 ]

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 [ 550998-53-3 ]

* 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 [ 550998-53-3 ]
Downstream synthetic route of [ 550998-53-3 ]

[ 550998-53-3 ] Synthesis Path-Upstream 1~6

1
[ 550998-53-3 ]
[ 1423-61-6 ]

Reference： [1] European Journal of Medicinal Chemistry, 2017, vol. 125, p. 538 - 550

2
[ 550998-53-3 ]
[ 19075-59-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium hydroxide In methanol for 2 h; Reflux	The second step in the preparation of methyl 7-bromo-benzo [b] thiophene-2- carboxylate 64 mg (0.22 mmol) was dissolved in a 3 ml of methanol and then, 3N sodium hydroxide, 240 ul (0.72 mmol) was added 2 hours and heated to reflux. The reaction mixture was acidified with 3N hydrochloric acid and extracted with ethyl acetate 30 ml. It was charged and the organic dried and concentrated under reduced pressure over anhydrous sodium sulfate (Na2SO4). To give the 62 mg yield as a white solid target compound without a residue purified by silica gel column chromatography 100percent (0.24 mmol).
96%	Stage #1: With potassium hydroxide In water for 3 h; Reflux Stage #2: With hydrogenchloride In water	General procedure: The solution of compound 2a or 2b (1.1 mmol) in water (10 mL)was stirred and then potassium hydroxide pellets (5.4 mmol) wasadded, which was refluxed for 3 h. The aqueous layer was thenacidified to pH 1 with 1 M hydrochloric acid solution. The aqueouslayer was extracted with dichloromethane (3 15 mL). The combinedorganic layers were dried with sodium sulfate, filtered, andthe solvents were removed under reduced pressure to afford thetitle compound 3a or 3b.
272 mg	With lithium hydroxide monohydrate In methanol; water at 75℃; for 2 h;	A mixture of 300 mg of methyl 7-bromobenzo[b]thiophene-2-carboxylate, 100 mg of lithium hydroxide monohydrate,3 ml of water, and 9 ml of methanol was stirred for 2 hours at 75°C. The reaction mixture was concentratedunder reduced pressure. Water was added to the residues, and the residue was washed three times with tert-butylmethyl ether. Concentrated hydrochloric acid was added to the aqueous layer, and then extraction was performed threetimes by using tert-butyl methyl ether. The collected organic layer was washed with saturated saline, dried over magnesiumsulfate, and then concentrated under reduced pressure, thereby obtaining 272 mg of 7-bromobenzo[b]thiophene-2-carboxylic acid (hereinafter, described as a "compound 13 of the present invention"). 1H-NMR (DMSO-D6) δ: 13.74 (br s, 1H), 8.27 (s, 1H), 8.06 (dd, 1H, J = 7.8, 0.9 Hz), 7.78 (dd, 1H, J = 7.8, 0.9 Hz), 7.44(t, 1H, J = 7.8 Hz).

Reference： [1] Patent: KR2015/117318, 2015, A, . Location in patent: Paragraph 0181; 0192; 0193; 0194
[2] European Journal of Medicinal Chemistry, 2017, vol. 125, p. 538 - 550
[3] Patent: WO2003/104227, 2003, A1, . Location in patent: Page 47, 48
[4] Patent: EP2926660, 2015, A1, . Location in patent: Paragraph 0262; 0263

3
[ 149947-15-9 ]
[ 2365-48-2 ]
[ 19075-59-3 ]
[ 550998-53-3 ]

Reference： [1] Patent: WO2004/13136, 2004, A1, . Location in patent: Page/Page column 37
[2] Patent: WO2003/104227, 2003, A1, . Location in patent: Page 47

4
[ 149947-15-9 ]
[ 2365-48-2 ]
[ 550998-53-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 15 h;	General procedure: To a stirred solution of compound 1a or 1b(9.90 mmol)in DMF(20 mL) was added methyl thioglycolate (10.9 mmol) and potassiumcarbonate (39.6 mmol). The resulting mixture was stirred at60 °C for 15 h. The DMF was removed under reduced pressure,water (50 mL) was added and the mixture was extracted with ethylacetate (2 40 mL). The combined organic layers were dried withsodium sulfate, filtered, and the solvents were removed underreduced pressure to afford the title compound 2a or 2b.
61%	Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5 h; Stage #2: at 0 - 20℃; for 1.25 h;	Methylthio glycolate 1,4 ml (15.96 mmol) to 30 ml of Ν, Ν-dimethylformamide to dissolve after which, 638 mg NaH (60percent, 15.96 mmol) was added and stirring at room temperature for 30 minutes at 0 C was added 3-bromo-2-fluoro benzaldehyde 2.16 g (10.64 mmol) prepared in Step 1 up to room temperature and then stirred for 15 minutes and the mixture was stirred for one hour.It was added to 50 ml of water and stirred for 5 minutes.And extracted with 50 ml of ethyl acetate, the organic layer over anhydrous sodium sulfate (Na₂S0₄dried) and concentrated under reduced pressure and the filtrate was purified by silica gel column chromatography (n nucleic acid: ethyl acetate, 50: 1, v / v) to give a white solid. to give the 1.75 g (6.45 mmol) of the desired compound in a yield of 61percent,

Reference： [1] European Journal of Medicinal Chemistry, 2017, vol. 125, p. 538 - 550
[2] Patent: KR2015/117318, 2015, A, . Location in patent: Paragraph 0181; 0187; 0188; 0189

5
[ 149947-15-9 ]
[ 2365-48-2 ]
[ 19075-59-3 ]
[ 550998-53-3 ]

Reference： [1] Patent: WO2004/13136, 2004, A1, . Location in patent: Page/Page column 37
[2] Patent: WO2003/104227, 2003, A1, . Location in patent: Page 47

6
[ 1072-85-1 ]
[ 550998-53-3 ]

Reference： [1] Patent: KR2015/117318, 2015, A,

[ 550998-53-3 ] Synthesis Path-Downstream 1~88

1
[ 149947-15-9 ]
[ 2365-48-2 ]
[ 19075-59-3 ]
[ 550998-53-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride;	Ausgehend von 27.8 g (137.1 mmol) 3-Brom-2-fluorbenzaldehyd werden mit 8.2 g. (205.7 mmol) Natriumhydrid (60%-ig in [PARaFFINoeL)] und 16.0 g [(150.] 9 mmol) [MERCAPTOESSIGSaeUREMETHYLESTER] 20.57 g eines Gemisches aus der Titelverbindung und der korrespondierenden Saeure (ca. 1 : 1) nach der allgemeinen Arbeitsvorschrift A erhalten.

Reference： [1]Patent: WO2004/13136,2004,A1 .Location in patent: Page/Page column 37
[2]Patent: WO2003/104227,2003,A1 .Location in patent: Page 47

2
[ 550998-53-3 ]
[ 19075-59-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium hydroxide; In methanol; for 2h;Reflux;	The second step in the preparation of methyl 7-bromo-benzo [b] thiophene-2- carboxylate 64 mg (0.22 mmol) was dissolved in a 3 ml of methanol and then, 3N sodium hydroxide, 240 ul (0.72 mmol) was added 2 hours and heated to reflux. The reaction mixture was acidified with 3N hydrochloric acid and extracted with ethyl acetate 30 ml. It was charged and the organic dried and concentrated under reduced pressure over anhydrous sodium sulfate (Na2SO4). To give the 62 mg yield as a white solid target compound without a residue purified by silica gel column chromatography 100% (0.24 mmol).
96%		General procedure: The solution of compound 2a or 2b (1.1 mmol) in water (10 mL)was stirred and then potassium hydroxide pellets (5.4 mmol) wasadded, which was refluxed for 3 h. The aqueous layer was thenacidified to pH 1 with 1 M hydrochloric acid solution. The aqueouslayer was extracted with dichloromethane (3 15 mL). The combinedorganic layers were dried with sodium sulfate, filtered, andthe solvents were removed under reduced pressure to afford thetitle compound 3a or 3b.
93%	With potassium hydroxide; In water; for 3h;Reflux;	General procedure: The solution of compound 2a-2n (1.1 mmol) in water (10 mL)was stirred and then potassium hydroxide pellets (5.4 mmol) wereadded, which was refluxed for 3 h. The aqueous layer was thenacidified to pH 1 with 1M hydrochloric acid solution. The aqueouslayer was extracted with dichloromethane (3 x 15 mL). The combinedorganic layers were dried with sodium sulfate, filtered, andthe solvents were removed under reduced pressure to afford thetitle compound 3a-3n [31,34].

91.0%		Ausgehend von 10.0 g (36.9 mmol) [7-BROM-L-BENZOTHIOPHEN-2-CARBONSaeUREMETHYL-] ester werden 8. [99 G] (91.0 % d. Th. ) des gewuenschten Produkts nach der allgemeinen Arbeitsvorschrift B erhalten. [H-NMR] (200 MHz, [DMSO-D6)] : [8] 13.76 (br. s, 1H), 8.28 [(S,] 1H), 8. [07] (d, 1H), 7.78 (d, 1H), 7.46 (dd, 1H). HPLC (Methode [1)] : Rt= 4.4 min.
272 mg	With lithium hydroxide monohydrate; In methanol; water; at 75℃; for 2h;	A mixture of 300 mg of methyl 7-bromobenzo[b]thiophene-2-carboxylate, 100 mg of lithium hydroxide monohydrate,3 ml of water, and 9 ml of methanol was stirred for 2 hours at 75C. The reaction mixture was concentratedunder reduced pressure. Water was added to the residues, and the residue was washed three times with tert-butylmethyl ether. Concentrated hydrochloric acid was added to the aqueous layer, and then extraction was performed threetimes by using tert-butyl methyl ether. The collected organic layer was washed with saturated saline, dried over magnesiumsulfate, and then concentrated under reduced pressure, thereby obtaining 272 mg of 7-bromobenzo[b]thiophene-2-carboxylic acid (hereinafter, described as a "compound 13 of the present invention"). 1H-NMR (DMSO-D6) delta: 13.74 (br s, 1H), 8.27 (s, 1H), 8.06 (dd, 1H, J = 7.8, 0.9 Hz), 7.78 (dd, 1H, J = 7.8, 0.9 Hz), 7.44(t, 1H, J = 7.8 Hz).

Reference： [1]Patent: KR2015/117318,2015,A .Location in patent: Paragraph 0181; 0192; 0193; 0194
[2]European Journal of Medicinal Chemistry,2017,vol. 125,p. 538 - 550
[3]European Journal of Medicinal Chemistry,2019,vol. 174,p. 236 - 251
[4]Patent: WO2003/104227,2003,A1 .Location in patent: Page 47, 48
[5]Patent: EP2926660,2015,A1 .Location in patent: Paragraph 0262; 0263

3
[ 550998-53-3 ]
[ 186498-02-2 ]
[ 634905-14-9 ]

Yield	Reaction Conditions	Operation in experiment
16.4%	With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In DMF (N,N-dimethyl-formamide); water; at 80℃; for 16h;	Zu einer Loesung von 619.1 mg (2.28 mmol) [7-BROM-L-BENZOTHIOPHEN-2-CARBON-] saeuremethylester (Beispiel 6A) und 520 mg (2.51 mmol) 4- (4-Morpholinyl) phenyl- boronsaeure in 10 mL DMF werden sukzessive 3.42 [ML] 2 M Natriumcarbonat- Loesung sowie 83.5 mg (0.11 mmol) PdC12 [(DPPF)] zugegeben. Es wird 16 h auf [80C] erhitzt. Nach dem Abkuehlen wird ueber Kieselgur filtriert und mittels praeparativer HPLC aufgereinigt. Das eingeengte Produkt wird im Hochvakuum getrocknet. Man erhaelt 146.7 mg (16.4 % d. Th. ) der Titelverbindung. HPLC (Methode [1)] : [RT] = 4.6 min. MS (ESIpos) : [NI/Z] = 354 (M+H) +.

Reference： [1]Patent: WO2003/104227,2003,A1 .Location in patent: Page 55, 56

4
[ 550998-53-3 ]
[ 13061-96-6 ]
[ 3751-50-6 ]

Yield	Reaction Conditions	Operation in experiment
402 mg	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 100℃; for 2.5h;Inert atmosphere;	12122] A mixture of 600 mg of methyl 7-bromobenzo[b] thiophene-2-carboxylate, 199 mg of methylboronic acid, 1.41 g of potassium phosphate, 181 mg of a [1,1?-bis(diphe- nylphosphino)ferrocene]palladium (II) dichloride dichloromethane adduct, 7 ml of 1 ,4-dioxane, and 0.12 ml of water was stirred for 2.5 hours at 100 C. under a nitrogen atmosphere. Afier being cooled to room temperature, the reaction mixture was concentrated under reduced pressure. Chloroform and water were added to the residues, and insoluble matter was separated by filtration. The filtrate was extracted using chloroform, and the organic layer was washed with saturated saline, dried over magnesium sulfate, and then concentrated under reduced pressure. The residues were subjected to silica gel colunm chromatography, thereby obtaining 402 mg of methyl 7-methylbenzo[b]thiophene-2- carboxylate (hereinafier, described as a ?compound 25 of the present invention?).12123] Compound 25 of the Present Invention12124] ?H-NMR (CDC13) oe: 8.09 (s, 1H), 7.74-7.72 (m,1H), 7.35-7.33 (m, 1H), 7.27-7.25 (m, 1H), 3.95 (s, 3H), 2.57(s, 3H).
402 mg	With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 100℃; for 2.5h;Inert atmosphere;	A mixture of 600 mg of <strong>[550998-53-3]methyl 7-bromobenzo[b]thiophene-2-carboxylate</strong>, 199 mg of methylboronic acid, 1.41g of potassium phosphate, 181 mg of a [1,1?-bis(diphenylphosphino)ferrocene]palladium (II) dichloride dichloromethaneadduct, 7 ml of 1,4-dioxane, and 0.12 ml of water was stirred for 2.5 hours at 100C under a nitrogen atmosphere. Afterbeing cooled to room temperature, the reaction mixture was concentrated under reduced pressure. Chloroform andwater were added to the residues, and insoluble matter was separated by filtration. The filtrate was extracted usingchloroform, and the organic layer was washed with saturated saline, dried over magnesium sulfate, and then concentratedunder reduced pressure. The residues were subjected to silica gel column chromatography, thereby obtaining 402 mgof methyl 7-methylbenzo[b]thiophene-2-carboxylate

Reference： [1]Patent: US2015/282482,2015,A1 .Location in patent: Paragraph 2122; 2123; 2124
[2]Patent: EP2926660,2015,A1 .Location in patent: Paragraph 0279

5
[ 550998-53-3 ]
[ 98-80-6 ]
methyl 7-phenylbenzo[b]thiophene-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; lithium chloride; In 1,4-dioxane; at 106℃; for 7h;Inert atmosphere;	To a solution of <strong>[550998-53-3]methyl 7-bromobenzo[b]thiophene-2-carboxylate</strong> ( 1.2 g, 4.4 mmol) in dioxane (15 mL) at room temperature under nitrogen was added potassium carbonate ( 1.2 g, 8.8 mmol), phenylboronic acid (0.64 g, 5.3 mmol), tetrakis(triphenylphosphine)palladium(0) (0.50 g, 0.44 mmol) and lithium chloride (0.53 g, 8.8 mmol). The mixture was stirred at 106 C for 7 hours, then diluted with water (30 mL) and extracted with ethyl acetate (3 chi 50 mL). The combined organic layers were washed with brine (2 x 50 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography [petroleum ether: ethyl acetate = 40: 1] to give compound B-234 (0.48 g, 40% yield) as a yellow solid.
118mg	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; lithium chloride; In 1,4-dioxane; water; at 100℃; for 4h;Inert atmosphere;	12160] A mixture of 750 mg of methyl 7-bromobenzo[b] thiophene-2-carboxylate, 438mg of phenyl boronic acid, 610 mg of lithium chloride, 528mg of sodium carbonate, 160mg of tetrakis(triphenylphosphine)palladium (0), 30 ml of 1,4- dioxane, and 15 ml of water was stirred for 4 hours at 100 C. in a nitrogen atmosphere. Afier being cooled to room temperature, the reaction mixture was concentrated under reduced pressure. Chloroform and water were added to the residues, and insoluble matter was separated by filtration. The aqueous layer was extracted twice by using chloroform, and the collected organic layer was washed with saturated saline, dried over magnesium sulfate, and then concentrated under reduced pressure. The residues were subjected to silica gel colunm chromatography, thereby obtaining 118mg ofmethyl 7-phenylbenzo[b]thiophene-2-carboxylate (hereinafter, described as a ?compound 37 of the present invention?). 12161] Compound 37 of the Present Invention12162] ?H-NMR (CDC13) oe: 8.14 (s, 1H), 7.88-7.86 (m,1H), 7.72-7.71 (m, 2H), 7.54-7.41 (m, 5H), 3.94 (s, 3H).
118 mg	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; lithium chloride; In 1,4-dioxane; water; at 100℃; for 4h;Inert atmosphere;	A mixture of 750 mg of <strong>[550998-53-3]methyl 7-bromobenzo[b]thiophene-2-carboxylate</strong>, 438 mg of phenyl boronic acid, 610mg of lithium chloride, 528 mg of sodium carbonate, 160 mg of tetrakis(triphenylphasphine)palladium (0), 30 ml of 1,4-dioxane, and 15 ml of water was stirred for 4 hours at 100C under a nitrogen atmosphere. After being cooled to roomtemperature, the reaction mixture was concentrated under reduced pressure. Chloroform and water were added to the residues, and insoluble matter was separated by filtration. The aqueous layer was extracted twice by using chloroform,and the collected organic layer was washed with saturated saline, dried over magnesium sulfate, and then concentratedunder reduced pressure. The residues were subjected to silica gel column chromatography, thereby obtaining 118 mgof methyl 7-phenylbenzo[b]thiophene-2-carboxylate

Reference： [1]Patent: WO2016/100184,2016,A1 .Location in patent: Paragraph 00530
[2]Patent: US2015/282482,2015,A1 .Location in patent: Paragraph 2160;' 2161; 2162
[3]Patent: EP2926660,2015,A1 .Location in patent: Paragraph 0315

6
[ 550998-53-3 ]
[ 17933-03-8 ]
methyl 7-(3-methylphenyl)benzo[b]thiophene-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
385 mg	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; lithium chloride; In 1,4-dioxane; water; at 100℃; for 3h;	12175] A mixture of 750 mg of methyl 7-bromobenzo[b] thiophene-2-carboxylate, 489mg of 3-methylphenyl boronic acid, 610mg of lithium chloride, 528mg of sodium carbonate, 160 ng of tetrakis(triphenylphosphine)palladium (0), 30 ml of 1 ,4-dioxane, and 15 ml of water was stirred for 3 hours at 1000 C. After being cooled to room temperature, the reaction mixture was concentrated under reduced pressure. Chloroform was added to the residues, and insoluble matter was separated by filtration. Afier water was added to the filtrate, extraction was performed by using chloroform. The organic layer was washed with saturated saline, dried over magnesium sulfate, and then concentrated under reduced pressure. The residues were subjected to silica gel colunm chromatography, thereby obtaining 385 mg of methyl 7-(3-methylphe- nyl)benzo[b]thiophene-2-carboxylate (hereinafter, described as a ?compound 42 of the present invention?).12176] Compound 42 of the Present Invention j2177] ?H-NMR (CDC13) oe: 8.13 (s, 1H), 7.86-7.84 (m, 1H), 7.52-7.46 (m, 4H), 7.41-7.39 (m, 1H), 7.26-7.23 (m, 1H), 3.94 (s, 3H), 2.45 (s, 3H).
385 mg	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; lithium chloride; In 1,4-dioxane; water; at 100℃; for 3h;	A mixture of 750 mg of <strong>[550998-53-3]methyl 7-bromobenzo[b]thiophene-2-carboxylate</strong>, 489 mg of 3-methylphenyl boronicacid, 610 mg of lithium chloride, 528 mg of sodium carbonate, 160 mg of tetrakis(triphenylphosphine)palladium (0), 30ml of 1,4-dioxane, and 15 ml of water was stirred for 3 hours at 100C. After being cooled to room temperature, thereaction mixture was concentrated under reduced pressure. Chloroform was added to the residues, and insoluble matterwas separated by filtration. After water was added to the filtrate, extraction was performed by using chloroform. Theorganic layer was washed with saturated saline, dried over magnesium sulfate, and then concentrated under reducedpressure. The residues were subjected to silica gel column chromatography, thereby obtaining 385 mg of methyl 7-(3-methylphenyl)benzo[b]thiophene-2-carboxylate.

Reference： [1]Patent: US2015/282482,2015,A1 .Location in patent: Paragraph 2175; 2176; 2177
[2]Patent: EP2926660,2015,A1 .Location in patent: Paragraph 0329

7
[ 550998-53-3 ]
[ 5720-06-9 ]
methyl 7-(2-methoxyphenyl)benzo[b]thiophene-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
543 mg	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; lithium chloride; In 1,4-dioxane; water; at 100℃; for 3h;	12181] A mixture of 750 mg of methyl 7-bromobenzo[b] thiophene-2-carboxylate, 575 mg of 2-methoxyphenyl boronic acid, 610 mg of lithium chloride, 528 mg of sodium carbonate, 160mg of tetrakis(triphenylphosphine)palladium (0), 30 ml of 1 ,4-dioxane, and 15 ml of water was stirred for 3 hours at 100C. After being cooled to room temperature, the reaction mixture was concentrated under reduced pressure. Chloroform was added to the residues, and insoluble matter was separated by filtration. Afier water was added to the filtrate, extraction was performed using chloroform. The organic layer was washed with saturated saline, dried over magnesium sulfate, and then concentrated under reduced pressure. The residues were subjected to silica gel colunm chromatography, thereby obtaining 543 mg of methyl 7-(2- methoxyphenyl)benzo[b]thiophene-2-carboxylate (hereinafter, described as a ?compound 44 of the present invention?). 12182] Compound 44 of the Present Invention j2183] ?H-NMR (CDC13) oe: 8.11 (s, 1H), 7.87-7.85 (m, 1H), 7.50-7.41 (m, 4H), 7.08-7.05 (m, 2H), 3.91 (s, 3H), 3.79 (s, 3H).
543 mg	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; lithium chloride; In 1,4-dioxane; water; at 20℃; for 3h;	A mixture of 750 mg of <strong>[550998-53-3]methyl 7-bromobenzo[b]thiophene-2-carboxylate</strong>, 575 mg of 2-methoxyphenyl boronicacid, 610 mg of lithium chloride, 528 mg of sodium carbonate, 160 mg of tetrakis(triphenylphosphine)palladium (0), 30ml of 1,4-dioxane, and 15 ml of water was stirred for 3 hours at 100C. After being cooled to room temperature, thereaction mixture was concentrated under reduced pressure. Chloroform was added to the residues, and insoluble matterwas separated by filtration. After water was added to the filtrate, extraction was performed using chloroform. The organiclayer was washed with saturated saline, dried over magnesium sulfate, and then concentrated under reduced pressure.The residues were subjected to silica gel column chromatography, thereby obtaining 543 mg of methyl 7-(2-methoxyphenyl)benzo[b]thiophene-2-carboxylate.

Reference： [1]Patent: US2015/282482,2015,A1 .Location in patent: Paragraph 2181; 2182; 2183
[2]Patent: EP2926660,2015,A1 .Location in patent: Paragraph 0335

8
[ 550998-53-3 ]
7-methylbenzo[b]thiophene-2-carboxylic acid [ No CAS ]

Reference： [1]Patent: EP2926660,2015,A1

9
[ 550998-53-3 ]
[ 98-80-6 ]
7-phenylbenzo[b]thiophene-2-carboxylic acid [ No CAS ]

Reference： [1]Patent: EP2926660,2015,A1
[2]Patent: WO2016/100184,2016,A1

10
[ 550998-53-3 ]
[ 17933-03-8 ]
7-(3-methylphenyl)benzo[b]thiophene-2-carboxylic acid [ No CAS ]

Reference： [1]Patent: EP2926660,2015,A1

11
[ 550998-53-3 ]
[ 5720-06-9 ]
7-(2-methoxyphenyl)benzo[b]thiophene-2-carboxylic acid [ No CAS ]

Reference： [1]Patent: EP2926660,2015,A1

12
[ 110-91-8 ]
[ 550998-53-3 ]
methyl 7-morpholinobenzo[b]thiophene-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; XPhos; In toluene; at 100℃; for 12h;Inert atmosphere;	Methyl 7-bromobenzo[6]thiophene-2-carboxylate (1.0 g, 3.7 mmol), morpholine (0.32 g, 3.7 mmol), cesium carbonate (2.4 g, 7.4 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.34 g, 0.37 mmol) and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.18 g, 0.37 mmol) in toluene (50 mL) was de-gassed and heated to 100 C for 12 hours under nitrogen. The reaction mixture was poured into water (40 mL) and extracted with ethyl acetate (120 mL). The organic phase was washed with brine (3 chi 20 mL), dried with anhydrous sodium sulfate, concentrated in vacuo and purified by column chromatography [petroleum ether: ethyl acetate = 10: 1] to afford the compound B-298 (0.95 g, crude) as a yellow gum. LCMS (B): tR=0.838 min., (ES+) m/z (M+H)+ = 278.1

Reference： [1]Patent: WO2016/100184,2016,A1 .Location in patent: Paragraph 00657-00658

13
[ 550998-53-3 ]
[ 287944-16-5 ]
methyl 7-(3,6-dihydro-2H-pyran-4-yl)benzo[b]thiophene-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 101℃; for 48h;Inert atmosphere;	To a solution of methyl 7-(3,6-dihydro-2H-pyran-4-yl)benzo[b]thiophene-2-carboxylate (1.0 g, 3.7 mmol) in dioxane (30 mL) and water (6 mL) under nitrogen was added K2C03 (1.5 g, 11 mmol), Pd(dppf)Cl2.CH2Cl2 (301 mg, 0.37 mmol) and 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5- tetramethyl-l,3,2-dioxaborolane (930 mg, 4.4 mmol). The mixture was stirred at 101 C for 48 hours. On completion, the reaction mixture was concentrated and purified by silica gel chromatography [petroleum ether: ethyl acetate = 16 : 1] to give compound B-211 (300 mg, 60% yield) as a white solid. -NMR (CD3OD, 400 MHz): delta 8.12 (s, 1H), 7.86 (dd, Ji=8.0 Hz, J2=1.6 Hz 1H), 7.48-7.42 (m, 2H), 6.35-6.34 (m, 1H), 4.39-4.36 (m, 2H), 4.00-3.97 (m, 2H), 3.93 (s, 3H), 2.62-2.59 (m, 2H).

Reference： [1]Patent: WO2016/100184,2016,A1 .Location in patent: Paragraph 00484

14
[ 550998-53-3 ]
7-cyclopropylbenzo[b]thiophene-2-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2016/100184,2016,A1

15
[ 550998-53-3 ]
methyl 7-(prop-1-an-2-yl)benzo[b]thiophene-2-carboxylate [ No CAS ]

Reference： [1]Patent: WO2016/100184,2016,A1

16
[ 550998-53-3 ]
7-isopropylbenzo[b]thiophene-2-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2016/100184,2016,A1

17
[ 550998-53-3 ]
methyl 7-(tetrahydro-2H-pyran-4-yl)benzo[b]thiophene-2-carboxylate [ No CAS ]

Reference： [1]Patent: WO2016/100184,2016,A1

18
[ 550998-53-3 ]
7-(tetrahydro-2H-pyran-4-yl)benzo[b]thiophene-2-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2016/100184,2016,A1

19
[ 550998-53-3 ]
methyl 7-(2,2,2-trifluoroethyl)benzo[b]thiophene-2-carboxylate [ No CAS ]

Reference： [1]Patent: WO2016/100184,2016,A1

20
[ 550998-53-3 ]
7-(2,2,2-trifluoroethyl)benzo[b]thiophene-2-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2016/100184,2016,A1

21
[ 550998-53-3 ]
7-(dimethylamino)benzo[b]thiophene-2-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2016/100184,2016,A1

22
[ 550998-53-3 ]
methyl 7-(thiazol-2-yl)benzo[b]thiophene-2-carboxylate [ No CAS ]

Reference： [1]Patent: WO2016/100184,2016,A1

23
[ 550998-53-3 ]
7-(thiazol-2-yl)benzo[b]thiophene-2-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2016/100184,2016,A1

24
[ 550998-53-3 ]
methyl 7-(1-methylcyclopropyl)benzo[b]thiophene-2-carboxylate [ No CAS ]

Reference： [1]Patent: WO2016/100184,2016,A1

25
[ 550998-53-3 ]
7-(1-methylcyclopropyl)benzo[b]thiophene-2-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2016/100184,2016,A1

26
[ 550998-53-3 ]
7-(methylsulfonyl)benzo[b]thiophene-2-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2016/100184,2016,A1

27
[ 550998-53-3 ]
7-morpholinobenzo[b]thiophene-2-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2016/100184,2016,A1

28
[ 550998-53-3 ]
methyl 7-(3-(trifluoromethyl)-4,5-dihydro-3H-pyrazol-3-yl)benzo[b]thiophene-2-carboxylate [ No CAS ]

Reference： [1]Patent: WO2016/100184,2016,A1

29
[ 550998-53-3 ]
methyl 7-(1-(trifluoromethyl)cyclopropyl)benzo[b]thiophene-2-carboxylate [ No CAS ]

Reference： [1]Patent: WO2016/100184,2016,A1

30
[ 550998-53-3 ]
7-(1-(trifluoromethyl)cyclopropyl)benzo[b]thiophene-2-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2016/100184,2016,A1

31
[ 550998-53-3 ]
(R)-N-(2,2-dimethylquinuclidin-3-yl)-7-isopropylbenzo[b]thiophene-2-carboxamide hydrochloride [ No CAS ]

Reference： [1]Patent: WO2016/100184,2016,A1

32
[ 550998-53-3 ]
potassium isopropenyltrifluoroborane [ No CAS ]
methyl 7-(prop-1-en-2-yl)benzo[b]thiophene-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With caesium carbonate; triphenylphosphine; palladium dichloride; In tetrahydrofuran; water; at 85℃; for 16h;Inert atmosphere;	A solution of potassium vinyltrifluoroborate (0.33 g, 2.2 mmol), palladium chloride (6.5 mg, 37 umol), triphenylphosphine (29 mg, 0.11 mmol), cesium carbonate (1.8 g, 5.5 mmol) and <strong>[550998-53-3]methyl 7-bromobenzo[b]thiophene-2-carboxylate</strong> (0.50 g, 1.8 mmol) in tetrahydrofuran (9 mL) and water (1 mL) was stirred under nitrogen at 85 C for 16 hours. On completion, the mixture was cooled to room temperature, diluted with water (10 mL) and extracted with dichloromethane (3 x 10 mL). The combined organic layers were washed with water (10 mL) and brine (10 mL) and concentrated in vacuo. The residue was purified by silica gel column chromatography [petroleum ether: ethyl acetate = 100: 1] to give compound B-206 (0.30 g, 70% yield) as an oil. LCMS (B): (ES+) m/z (M+H)+ = 233.0, tR=0.997.

Reference： [1]Patent: WO2016/100184,2016,A1 .Location in patent: Paragraph 00473-00474

33
[ 550998-53-3 ]
[ 73183-34-3 ]
methyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophene-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 100℃;Inert atmosphere;	To a mixture of <strong>[550998-53-3]methyl 7-bromobenzo[b]thiophene-2-carboxylate</strong> (1.0 g, 3.7 mmol) in N, N-dimethylformamide (10 mL) under nitrogen was added 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2- dioxaborolane) (1.9 g, 7.4 mmol), [l,l'-bis(diphenylphosphino)ferrocene]dichloropalladium (0.27 g, 0.37 mmol) and potassium acetate (1.1 g, 11 mmol). The mixture was stirred at 100 C overnight. On completion, the mixture was poured into water (20 mL) and extracted with ethyl acetate (2 chi 50 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography [petroleum ether: ethyl acetate = 20: 1] to give compound B-224 (1.0 g, 55% yield) as a white solid. LCMS (DD): tR=1.182 min., (ES+) m/z (M+H) =319.1.

Reference： [1]Patent: WO2016/100184,2016,A1 .Location in patent: Paragraph 00509-00510

34
[ 550998-53-3 ]
[ 506-59-2 ]
methyl 7-(dimethylamino)benzo[b]thiophene-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; XPhos; In 1,4-dioxane; at 120℃; for 4h;Microwave irradiation; Inert atmosphere;	Methyl 7-bromobenzothiophene-2-carboxylate (600 mg, 2.2 mmol), cesium carbonate (2.2 g, 6.6 mmol), tris(dibenzylideneacetone)dipalladium(0) (405 mg, 0.44 mmol), 2- (dicyclohexylphosphino)-2',4',6'-triisopropylbiphenyl (421 mg, 0.88 mmol), and N- methylmethanamine hydrochloride (1.1 g, 13 mmol) in dioxane (10 mL) were placed in a microwave reaction vessel. The mixture was degassed by bubbling nitrogen through it for 6 min. The reaction was heated by microwave irradiation at 120 C for 4 hours. On completion, the solvent was evaporated. The residue was purified by silica gel column chromatography [petroleum ether] to give compound B-227 (1.0 g, crude) as a green solid.

Reference： [1]Patent: WO2016/100184,2016,A1 .Location in patent: Paragraph 00515-00516

35
[ 550998-53-3 ]
[ 20277-69-4 ]
methyl 7-(methylsulfonyl)benzo[b]thiophene-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With copper(l) iodide; In 1-methyl-pyrrolidin-2-one; at 140℃; for 8h;Inert atmosphere;	A mixture of methyl 7-bromobenzo[6]thiophene-2-carboxylate (1.0 g, 3.7 mmol), sodium methanesulfinate (1.7 g, 17 mmol) and copper iodide (3.2 g, 17 mmol) in N-methyl-2-pyrrolidone (25 mL) was de-gassed and then heated to 140 C for 8 hours under nitrogen. The mixture was diluted with ethyl acetate (500 mL), filtered, washed with brine (6 chi 50 mL), dried with anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography [petroleum ether: ethyl acetate = 5: 1 to 10: 1] to afford compound B-296 (0.42 g, 42% yield) as a yellow solid. -NMR (CD3OD, 400 MHz): 8.28 (d, J=8.0 Hz, IH), 8.24 (s, IH), 8.10 (d, J=8.0 Hz, IH), 7.69 (t, J=8.0 Hz, IH), 3.95 (s, 3H), 3.20 (s, 3H).

Reference： [1]Patent: WO2016/100184,2016,A1 .Location in patent: Paragraph 00653-00654

36
[ 550998-53-3 ]
[ 1011460-68-6 ]
methyl 7-(3,3,3-trifluoroprop-1-en-2-yl)benzo[b]thiophene-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium phosphate; chloro(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1'-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) methyl tert-butyl ether; In tetrahydrofuran; water; at 60℃; for 12h;Inert atmosphere;	To a mixture of methyl 7-bromobenzo[6]thiophene-2-carboxylate (0.60 g, 2.2 mmol) in tetrahydrofuran (20 mL) and water (6 mL) under nitrogen was added 4,4,6-trimethyl-2 -(3,3,3- trifluoroprop-l-en-2-yl)-l,3,2-dioxaborinane (0.59 g, 2.7 mmol), potassium phosphate (0.94 g, 4.4 mmol) and [2-(2-aminophenyl)phenyl]-chloro-palladium;dicyclohexyl-[3-(2,4,6- triisopropylphenyl)phenyl]phosphane (87 mg, 0.11 mmol). The mixture was stirred at 60 C for 12 hours, then added into water (10 mL) and extracted with ethyl acetate (2 chi 20 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography [petroleum ether: ethyl acetate = 20: 1] to give compound B- 304 (0.60 g, 95% purity, 90% yield) as a yellow solid. LCMS (B): tR=0.906 min., (ES+) m/z (M+H)+ =287.1

Reference： [1]Patent: WO2016/100184,2016,A1 .Location in patent: Paragraph 00669-00670

37
[ 550998-53-3 ]
[ 411235-57-9 ]
methyl 7-cyclopropylbenzo[b]thiophene-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In 1,4-dioxane; water; at 100℃; for 4h;Inert atmosphere;	A mixture of <strong>[550998-53-3]methyl 7-bromobenzo[b]thiophene-2-carboxylate</strong> (1.0 g, 3.7 mmol), cyclopropylboronic acid (0.38 g, 4.4 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.26 g, 0.37 mmol) and potassium carbonate (1.5 g, 11 mmol) in dixoane (15 mL) and water (3 ml) was stirred at 100 C under nitrogen for 4 hours. On completion, the solution was diluted with water (20 mL) and extracted with ethyl acetate (2 chi 40 mL). The combined organic layers were concentrated in vacuo to give compound B-204 (0.70 g, crude) as a yellow solid, used for the next step without further purification.

Reference： [1]Patent: WO2016/100184,2016,A1 .Location in patent: Paragraph 00469-00470

38
[ 149947-15-9 ]
[ 2365-48-2 ]
[ 550998-53-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 15h;	General procedure: To a stirred solution of compound 1a or 1b(9.90 mmol)in DMF(20 mL) was added methyl thioglycolate (10.9 mmol) and potassiumcarbonate (39.6 mmol). The resulting mixture was stirred at60 C for 15 h. The DMF was removed under reduced pressure,water (50 mL) was added and the mixture was extracted with ethylacetate (2 40 mL). The combined organic layers were dried withsodium sulfate, filtered, and the solvents were removed underreduced pressure to afford the title compound 2a or 2b.
94%	With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 15h;	General procedure: To a stirred solution of compound 1a-1n (9.90 mmol) in DMF (20 mL) were added methyl thioglycolate (10.9 mmol) and potassium carbonate (39.6 mmol). The resulting mixture was stirred at 60 C for 15 h. The DMF was removed under reduced pressure,water (50 mL) was added and the mixture was extracted with ethylacetate (2 x 40 mL). The combined organic layers were dried withsodium sulfate, filtered, and the solvents were removed under reduced pressure to afford the title compound 2a-2n [31,34].
61%		Methylthio glycolate 1,4 ml (15.96 mmol) to 30 ml of Nu, Nu-dimethylformamide to dissolve after which, 638 mg NaH (60%, 15.96 mmol) was added and stirring at room temperature for 30 minutes at 0 C was added 3-bromo-2-fluoro benzaldehyde 2.16 g (10.64 mmol) prepared in Step 1 up to room temperature and then stirred for 15 minutes and the mixture was stirred for one hour.It was added to 50 ml of water and stirred for 5 minutes.And extracted with 50 ml of ethyl acetate, the organic layer over anhydrous sodium sulfate (Na2S04dried) and concentrated under reduced pressure and the filtrate was purified by silica gel column chromatography (n nucleic acid: ethyl acetate, 50: 1, v / v) to give a white solid. to give the 1.75 g (6.45 mmol) of the desired compound in a yield of 61%,

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 125,p. 538 - 550
[2]European Journal of Medicinal Chemistry,2019,vol. 174,p. 236 - 251
[3]Patent: KR2015/117318,2015,A .Location in patent: Paragraph 0181; 0187; 0188; 0189

39
[ 1072-85-1 ]
[ 550998-53-3 ]

Reference： [1]Patent: KR2015/117318,2015,A

40
[ 550998-53-3 ]
7-((4-chlorophenyl)amino)benzo[b]thiophene-1,1-dioxide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 125,p. 538 - 550

41
[ 550998-53-3 ]
7-((3,5-dimethylphenyl)amino)benzo[b]thiophene-1,1-dioxide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 125,p. 538 - 550

42
[ 550998-53-3 ]
7-((perfluorophenyl)amino)benzo[b]thiophene-1,1-dioxide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 125,p. 538 - 550

43
[ 550998-53-3 ]
7-((3-fluorophenyl)amino)benzo[b]thiophene-1,1-dioxide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 125,p. 538 - 550

44
[ 550998-53-3 ]
7-(p-tolylamino)benzo[b]thiophene-1,1-dioxide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 125,p. 538 - 550

45
[ 550998-53-3 ]
7-((4-methoxyphenyl)amino)benzo[b]thiophene-1,1-dioxide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 125,p. 538 - 550

46
[ 550998-53-3 ]
7-((2-methoxyphenyl)amino)benzo[b]thiophene-1,1-dioxide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 125,p. 538 - 550

47
[ 550998-53-3 ]
7-((3,4-difluorophenyl)amino)benzo[b]thiophene-1,1-dioxide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 125,p. 538 - 550

48
[ 550998-53-3 ]
7-((3,4-dichlorophenyl)amino)benzo[b]thiophene-1,1-dioxide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 125,p. 538 - 550

49
[ 550998-53-3 ]
7-((2-(trifluoromethyl)phenyl)amino)benzo[b]thiophene-1,1-dioxide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 125,p. 538 - 550

50
[ 550998-53-3 ]
7-bromobenzo[b]thiophene-1,1-dioxide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 125,p. 538 - 550

51
[ 550998-53-3 ]
7-((3,4,5-trimethoxyphenyl)amino)benzo[b]thiophene-1,1-dioxide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 125,p. 538 - 550

52
[ 550998-53-3 ]
[ 1423-61-6 ]

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 125,p. 538 - 550

53
[ 550998-53-3 ]
7-((3-(trifluoromethyl)phenyl)amino)benzo[b]thiophene-1,1-dioxide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 125,p. 538 - 550

54
[ 550998-53-3 ]
7-((4-(trifluoromethoxy)phenyl)amino)benzo[b]thiophene-1,1-dioxide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 125,p. 538 - 550

55
[ 550998-53-3 ]
7-((4-(trifluoromethyl)phenyl)amino)benzo[b]thiophene-1,1-dioxide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 125,p. 538 - 550

56
[ 550998-53-3 ]
N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-bromo-1-benzothiophene-2-carboxamide [ No CAS ]