[ CAS No. 550998-58-8 ] {[proInfo.proName]}

Name: 550998-58-8|Methyl 6-methoxybenzo[b]thiophene-2-carboxylate|95%
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SKU: A758835
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3d Animation Molecule Structure of 550998-58-8

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Quality Control of [ 550998-58-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 550998-58-8 ]

SDS Specification

Alternatived Products of [ 550998-58-8 ]

Product Details of [ 550998-58-8 ]

CAS No. :	550998-58-8	MDL No. :	MFCD07371543
Formula :	C₁₁H₁₀O₃S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VMGJIYVZMYUFSI-UHFFFAOYSA-N
M.W :	222.26	Pubchem ID :	53486111
Synonyms :

Calculated chemistry of [ 550998-58-8 ] Expand+

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.18
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	59.6
TPSA :	63.77 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) :	-5.45 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.65
Log Po/w (XLOGP3) :	3.1
Log Po/w (WLOGP) :	2.7
Log Po/w (MLOGP) :	1.94
Log Po/w (SILICOS-IT) :	3.48
Consensus Log Po/w :	2.77

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.42
Solubility :	0.0851 mg/ml ; 0.000383 mol/l
Class :	Soluble
Log S (Ali) :	-4.11
Solubility :	0.0174 mg/ml ; 0.0000781 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-3.55
Solubility :	0.0621 mg/ml ; 0.000279 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.24

Safety of [ 550998-58-8 ]

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 [ 550998-58-8 ]

* 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 [ 550998-58-8 ]

[ 550998-58-8 ] Synthesis Path-Downstream 1~22

1
[ 59812-35-0 ]
[ 550998-58-8 ]
dimethyl 6,6'-dimethoxy-3,3'-bi(1-benzothiophene)-2,2'-dicarboxylate [ No CAS ]

Reference： [1]Collection of Czechoslovak Chemical Communications,2003,vol. 68,p. 1020 - 1038

2
[ 331-64-6 ]
[ 2365-48-2 ]
[ 550998-58-8 ]

Yield	Reaction Conditions	Operation in experiment
84%	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].
21%	With triethylamine; In N,N-dimethyl-formamide; at 100℃; for 72h;	6-Methoxy-benzo[Z>]thiophene-2-carboxylic acid methyl ester (141-B).; To a solution of compound 141-A (21.4 g; 139 mmol) in anhydrous DMF (165 mL) was added triethylamine (25.2 mL; 181 mmol) followed methyl thioglycolate (5.3 mL; 278 mmol) and the reaction was heated at 100 C for 72 h. The reaction was cooled, partitioned between EtOAc and H2O, the layers separated, the aqueous phase extracted with EtOAc, the organic extracts combined, washed with 3N NaOH, H2O, brine, dried over Na2SO4, filtered, and the solvent evaporated under reduced pressure. The crude residue was triturated with CH2Cl2-heptanes, filtered, and the solid washed with heptanes and dried overnight to afford compound 141-B. The filtrate was evaporated and purified by flash column chromatography (SiO2) eluting with a heptane-EtOAc <n="214"/>gradient to afford a second crop of compound 141-B. The combined yield of the two crops afforded a white solid (6.55 g, 21%). 1H-NMR (DMSO-d6): delta 3.85 (s, 3H), 3.86 (s, 3H), 7.07-7.10 (m, IH), 7.63 (s, IH), 7.89-7.91 (d, IH), 8.11 (s, IH); MS: m/z 223.0 (MH+).
21%	With triethylamine; In N,N-dimethyl-formamide; at 100℃; for 72h;	Example 6 6-methoxy-benzo[b]thiophene-2-carboxylic acid methyl ester (141-B). To a solution of compound 141-A (21.4 g; 139 mmol) in anhydrous DMF (165 mL) was added triethylamine (25.2 mL; 181 mmol) followed methyl thioglycolate (5.3 mL; 278 mmol) and the reaction was heated at 100 C. for 72 h. The reaction was cooled, partitioned between EtOAc and H2O, the layers separated, the aqueous phase extracted with EtOAc, the organic extracts combined, washed with 3N NaOH, H2O, brine, dried over Na2SO4, filtered, and the solvent evaporated under reduced pressure. The crude residue was triturated with CH2Cl2-heptanes, filtered, and the solid washed with heptanes and dried overnight to afford compound 141-B. The filtrate was evaporated and purified by flash column chromatography (SiO2) eluting with a heptane-EtOAc gradient to afford a second crop of compound 141-B. The combined yield of the two crops afforded a white solid (6.55 g, 21%). 1H-NMR (DMSO-d6): delta 3.85 (s, 3H), 3.86 (s, 3H), 7.07-7.10 (m, 1H), 7.63 (s, 1H), 7.89-7.91 (d, 1H), 8.11 (s, 1H); MS: m/z 223.0 (MH+).

Step 1: a] 6-Methoxy-benzo[b]thiophene-2-carboxylic acid methyl ester To a solution of methyl thioglycolate (1.29 mL, 14 mmol, 1.1 eq.) in 22 mL of DMSO was added Nail 50% (0.972 g, 20 mmol, 1.56 eq.) and the mixture was stirred for 5 Min., before 2-fluoro-4-methoxybenzaldehyde (2.00 g, 13 mmol) was added (strongly exothermic). When the internal temperature had reached again 25 C., the reaction mixture was poured onto crashed ice and the precipitate filtered off, washed with water, and dried to obtain 1.896 g of the title compound as light yellow crystals.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 174,p. 236 - 251
[2]Patent: WO2009/12430,2009,A1 .Location in patent: Page/Page column 211-212
[3]Patent: US2012/190674,2012,A1 .Location in patent: Page/Page column 87
[4]Journal of Medicinal Chemistry,2007,vol. 50,p. 4793 - 4807
[5]Patent: US2009/29976,2009,A1 .Location in patent: Page/Page column 20

3
[ 550998-58-8 ]
[ 1029720-28-2 ]

Yield	Reaction Conditions	Operation in experiment
82.6%		Dissolve methyl 6-methoxybenzo [b] thiophene-2-carboxylate (0.25 g, 1.12 mmol) in dichloromethane (5 mL) in an argon atmosphere in a 100 mL round-bottom flask. 1M BBr3 in DCM (boron tribromide, 2.2 mL, 2.24 mmol) is added at 0 C, and the mixture is stirred at the same temperature for 2 hours. Thereafter it is stirred for 2 hours at room temperature. Methanol was added at 0 C. and stirred at room temperature for 30 minutes. After completion of the reaction, the mixture was extracted with ethyl acetate (30 mL x 3), Na2SO4 was added to remove water, the solvent was removed using a rotary concentrator, and the residue was separated by column chromatography (hexanes: ethyl acetate = 8: 1). Methyl 6-hydroxybenzo [b] thiophene-2-carboxylate (0.19 g, 0.91 mmol, 82.6%) was obtained.
		Step 2 6-Hydroxy-benzo[b]thiophene-2-carboxylic acid methyl ester The above prepared <strong>[550998-58-8]6-methoxy-benzo[b]thiophene-2-carboxylic acid methyl ester</strong> (0.200 g, 0.900 mmol) was dissolved in 5.5 mL of CH2Cl2, cooled to 0 C., and treated with BBr3 (1.90 mL of 1M solution in CH2Cl2, 2 eq.). After 3 additional h at ambient temperature, the reaction mixture was carefully poured onto crashed ice, twofold extracted with AcOEt, washed with water and brine, dried over magnesium sulfate, and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=8/2) gave 0.061 g of the title compound as light brown solid.

Reference： [1]Patent: KR101985005,2019,B1 .Location in patent: Paragraph 0088-0090; 0109-0110; 0112-0113
[2]Patent: US2009/29976,2009,A1 .Location in patent: Page/Page column 20

4
[ 550998-58-8 ]
[ 102539-79-7 ]

Yield	Reaction Conditions	Operation in experiment
98%		6-Methoxy-benzo[Z>]thiophene-2-carboxylic acid (141-C). ; To a solution of compound 141-B (6.55 g; 29.4 mmol) in methanol (100 mL) was added IN NaOH (44.2 mL; 44.2 mmol) and the reaction was heated at 65 C for 18 h. The reaction was cooled, the solvent evaporated under reduced pressure, the residue dissolved in H2O, cooled to 0 C, acidified with 2N HCl, and the solid filtered, washed with H2O, and dried in vacuo to afford compound 141-C as a white solid (6.01 g, 98%). 1H-NMR (DMSO-rfbeta): delta 3.84 (s, 3H), 7.05-7.08 (m, IH), 7.60-7.61 (d, IH), 7.87-7.89 (d, IH), 8.01 (s, IH), 13.24 (s, IH); MS: m/z 208.9 (MH+).
98%	With methanol; sodium hydroxide; at 65℃; for 18h;	6-methoxy-benzo[b]thiophene-2-carboxylic acid (141-C). To a solution of compound 141-B (6.55 g; 29.4 mmol) in methanol (100 mL) was added 1N NaOH (44.2 mL; 44.2 mmol) and the reaction was heated at 65 C. for 18 h. The reaction was cooled, the solvent evaporated under reduced pressure, the residue dissolved in H2O, cooled to 0 C., acidified with 2N HCl, and the solid filtered, washed with H2O, and dried in vacuo to afford compound 141-C as a white solid (6.01 g, 98%). 1H-NMR (DMSO-d6): delta 3.84 (s, 3H), 7.05-7.08 (m, 1H), 7.60-7.61 (d, 1H), 7.87-7.89 (d, 1H), 8.01 (s, 1H), 13.24 (s, 1H); MS: m/z 208.9 (MH+).
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].

Reference： [1]Patent: WO2009/12430,2009,A1 .Location in patent: Page/Page column 211-212
[2]Patent: US2012/190674,2012,A1 .Location in patent: Page/Page column 87
[3]European Journal of Medicinal Chemistry,2019,vol. 174,p. 236 - 251

5
[ 550998-58-8 ]
[ 1104630-87-6 ]