[ CAS No. 50551-57-0 ]

Name: 50551-57-0|Ethyl 6-methoxybenzofuran-2-carboxylate|97%
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Quality Control of [ 50551-57-0 ]

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Product Details of [ 50551-57-0 ]

CAS No. :	50551-57-0	MDL No. :	MFCD14279719
Formula :	C₁₂H₁₂O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VBJGXQIHVLKHCT-UHFFFAOYSA-N
M.W :	220.22 g/mol	Pubchem ID :	11830962
Synonyms :

Calculated chemistry of [ 50551-57-0 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.25
Num. rotatable bonds :	4
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	58.79
TPSA :	48.67 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) :	-5.5 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.89
Log Po/w (XLOGP3) :	3.02
Log Po/w (WLOGP) :	2.62
Log Po/w (MLOGP) :	1.37
Log Po/w (SILICOS-IT) :	2.6
Consensus Log Po/w :	2.5

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.26
Solubility :	0.121 mg/ml ; 0.000549 mol/l
Class :	Soluble
Log S (Ali) :	-3.71
Solubility :	0.0432 mg/ml ; 0.000196 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.9
Solubility :	0.0275 mg/ml ; 0.000125 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.66

Safety of [ 50551-57-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 50551-57-0 ]

* 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 [ 50551-57-0 ]

[ 50551-57-0 ] Synthesis Path-Downstream 1~55

1
[ 50551-57-0 ]
[ 50551-61-6 ]

Yield	Reaction Conditions	Operation in experiment
91%		To a stirred solution of Product of Step B (0.25 g, 1.21 mmol) in a mixture of THF, MeOH and H2O (5 ml : 2 ml : 1 ml), LiOH (0.145 g, 6 mmol) in H2O (0.5 ml) was added and the mixture was stirred for 3 h at room temp. The solvents were distilled off and the residue was portioned between EtOAc (20 ml) and 1 M HCI (2 ml). The organic layer was washed with H2O, dried over MgSO4 and filtered. The filtrate was evaporated to dryness to give the title compound (0.21 g, 91 %), as a colourless solid. 1H-NMR (DMSO-de) 7.61 (d, 1 H, J = 8.67 Hz); 7.54 (s, 1 H); 7.24 (d, 1 H, J = 1 .59 Hz); 6.93 (dd, 1 H, J = 8.67, 2.4 Hz); 3.8 (s, 3H).
83%	With sodium hydroxide; In 1,4-dioxane; at 40℃; for 0.5h;	Compound 38 (1.1 g, 5 mmol)was dissolved in 20mL of dioxane,and 8.0 mL of 1 N NaOH was added. The solution initially becameturbid but clarified upon completion of the reaction after 30 min.The dioxane was removed by distillation under reduced pressure,and the remaining productwas dissolved inwater. The solutionwasmixed with dichloromethane and after stratification, the organicphase was discarded, and the aqueous phase was adjusted to pH = 3 with 10% HCl. The precipitate was collected and recrystallizedin dry methanol. Finally, 0.51 g (yield of 83%) of solid wasobtained. m.p: 195-196 C. 1H NMR (600 MHz, DMSO-d6) delta (ppm):3.84 (s, 3H), 6.97 (dd, J1=9.0 Hz, J2 = 1.8 Hz, 1H), 729 (d, J=1.8 Hz,1H), 7.59 (s, 1H), 7.64 (d, J= 9.0 Hz, 1H), 13.32 (s, 1H).
79%	With sodium hydroxide; In 1,4-dioxane; at 20℃; for 2h;	The ice bath condition 2- Hdroxyl ,-4- methoxybenzaldehyde,and anhydrous K2c03 ( 2.2g15.6mmo 1) Dissolved inDMF(30ml) slowlydripping bromo Ethylacetate(2.2g13mmo 1)drippingis finished 0C stirring , 30min, then at 60C oil bath reaction 12h Thereaction liquid is poured into the ice waterfilter chloroform soluble solidsanhydrousNa2s04 drying, filtration, rotary dry solvent silica gel column chromatographyseparation , get yellow solid 2.31g , 2.31g (yield as 80%), will it,soluble Dioxane,[20ml]added sodium hydroxide solution [12ml] normalatmospheric temperature stir 2Hours Dioxane steameddry, The remaining liquid is poured intoice water. use dichloromethanewashing adjustingPHValue to 2 filter collect solid1.64g (yield as 79%), dissolve it in dichloromethane (30ml)addedN.N Diisopropylcarbodiimide(DIC)(1.06g8.41mmol) normal atmospherictemperature stirring 1 hour after added ,-4-Dimethylaminopyridine (DMAP0.17g1.39mmo l) Diethyl(hydroxymethyl)phosphonate 1.44g,8.57mmo I)Heating reflux 6 hours after usewith full water and edible salt washingreaction solutionanhydrous magnesium sulphate dry filtering after steam drying, Ethyl acetatepetroleum ether system recrystallization obtainedproduct -6-methoxy benzofurane,-2-carboxylic acid (2?_Diethylphosphonatemethyl ester products 2.48g (yield for 85%).

With sodium hydroxide; In water; N,N-dimethyl-formamide; at 60℃; for 0.5h;

General procedure: To a solution of intermediates 3a-3q (1mmol) in 10ml DMF, 2.0mL of 20% sodium hydroxide solution was dropped at 60C to carry out the ester hydrolysis reaction for 30min. Afterwards, the mixture was cooled to room temperature, and the PH value of the solution was adjusted to 2 using 10% hydrochloric acid, then the mixture was extracted with ethyl acetate. The organic phase was combined and condensed by vacuum concentration to afford the crude product, which was purified by recrystallization to give the designed compounds (4a-4q).

Reference： [1]Patent: WO2010/43000,2010,A1 .Location in patent: Page/Page column 94
[2]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 4939 - 4946
[3]Journal of Medicinal Chemistry,2017,vol. 60,p. 5472 - 5492
[4]European Journal of Medicinal Chemistry,2020,vol. 200
[5]Patent: CN103130705,2016,B .Location in patent: Paragraph 0174-0176
[6]Journal of the Chemical Society,1940,p. 787,791
[7]Journal of Medicinal Chemistry,1984,vol. 27,p. 570 - 576
[8]Journal of the American Chemical Society,1996,vol. 118,p. 7101 - 7107
[9]European Journal of Medicinal Chemistry,2020,vol. 190

2
[ 76322-06-0 ]
[ 50551-57-0 ]

Yield	Reaction Conditions	Operation in experiment
77%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; at 160℃; for 3h;	A mixture of the product of Step A (1 .28 g, 5.37 mmol) and DBU (0.3 ml) was heated for 3 h at 160 5C with stirring, cooled to room temperature and dissolved in EtOAc: MeOH mixture (99:1 ). The mixture was filtered through the silica bead and the filtrate was evaporated to give the title compound (1 .1 1 g; 77%), as colourless solid. 1H- NMR (CDCI3) 1.40 (tr, 3H, J = 7.13 Hz); 3.85 (s, 3H); 4.40 (q, 2H, J = 7.13, 14.25 Hz); 4.45 (s, 1 H); 6.91 (dd, 1 H, J = 2.25, 8.68 Hz); 7.04 (d, 1 H, J = 1.87 Hz); 7.51 (d, 1 H, J = 5.17 Hz),
77%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; at 160℃; for 3h;	mixture of the product of Step A (1 .28 g, 5.37 mmol) and DBU (0.3 ml) was heated for 3 h at 160 5C with stirring, cooled to room temperature and dissolved in EtOAc : MeOH mixture (99:1 ). The mixture was filtered through the silica bead and the filtrate was evaporated to give the title compound (1 .1 1 g; 77%), as colourless solid. 1H- NMR (CDCI3) 1.40 (tr, 3H, J = 7.13 Hz); 3.85 (s, 3H); 4.40 (q, 2H, J = 7.13, 14.25 Hz); 4.45 (s, 1 H); 6.91 (dd, 1 H, J = 2.25, 8.68 Hz); 7.04 (d, 1 H, J = 1 .87 Hz); 7.51 (d, 1 H, J = 5.17 Hz),
	With potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 3h;	General procedure: Compound 2a-2q(1 mmol) and K2CO3 (3 mmol) were suspended in DMF (10 mL), and the reaction mixture was warmed upto 120 C and refluxed for 3h, and then cooled to room temperature. The precipitation was separated out and purified by recrystallization to get the products 3a-3q.

Reference： [1]Patent: WO2010/43000,2010,A1 .Location in patent: Page/Page column 94
[2]Patent: WO2010/42998,2010,A1 .Location in patent: Page/Page column 67
[3]Journal of the Chemical Society,1940,p. 787,791
[4]European Journal of Medicinal Chemistry,2020,vol. 190

3
[ 673-22-3 ]
[ 685-87-0 ]
[ 50551-57-0 ]

Reference： [1]Journal of Medicinal Chemistry,1984,vol. 27,p. 570 - 576
[2]Journal of the American Chemical Society,1996,vol. 118,p. 7101 - 7107

4
[ 150-19-6 ]
[ 4504-12-5 ]
[ 50551-57-0 ]

Reference： [1]Australian Journal of Chemistry,1996,vol. 49,p. 1315 - 1323

6
[ 50551-57-0 ]
[ 178628-81-4 ]

Reference： [1]Journal of the American Chemical Society,1996,vol. 118,p. 7101 - 7107

7
[ 50551-57-0 ]
C₂₂H₂₂N₂O₉ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1996,vol. 118,p. 7101 - 7107

8
[ 50551-57-0 ]
[ 41910-91-2 ]

Reference： [1]Journal of Medicinal Chemistry,1984,vol. 27,p. 570 - 576

9
[ 50551-57-0 ]
6-Methoxy-2,3-dihydro-benzofuran-2-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1984,vol. 27,p. 570 - 576

10
[ 50551-57-0 ]
6-Methoxy-2,3-dihydro-benzofuran-2-carbonyl chloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1984,vol. 27,p. 570 - 576

11
[ 50551-57-0 ]
6-Methoxy-2,3-dihydro-benzofuran-2-carboxylic acid amide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1984,vol. 27,p. 570 - 576

12
[ 50551-57-0 ]
[ 89197-14-8 ]

Reference： [1]Journal of Medicinal Chemistry,1984,vol. 27,p. 570 - 576

13
[ 50551-57-0 ]
[ 89197-46-6 ]

Reference： [1]Journal of Medicinal Chemistry,1984,vol. 27,p. 570 - 576

14
[ 50551-57-0 ]
[ 860184-19-6 ]

Reference： [1]Journal of the Chemical Society,1940,p. 787,791

15
[ 50551-57-0 ]
[ 50963-49-0 ]

Reference： [1]Journal of the Chemical Society,1940,p. 787,791
[2]European Journal of Medicinal Chemistry,2020,vol. 200

16
[ 50551-57-0 ]
(6-methoxy-benzofuran-2-yl)-glyoxylonitrile [ No CAS ]

Reference： [1]Journal of the Chemical Society,1940,p. 787,791

17
[ 50551-57-0 ]
(6-methoxy-benzofuran-2-yl)-acetic acid [ No CAS ]

Reference： [1]Journal of the Chemical Society,1940,p. 787,791

18
[ 50551-57-0 ]
[ 859984-00-2 ]

Reference： [1]Journal of the Chemical Society,1940,p. 787,791

19
[ 673-22-3 ]
[ 105-36-2 ]
[ 50551-57-0 ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 60℃; for 12.5h;	The ice bath condition 2- Hdroxyl ,-4- methoxybenzaldehyde,and anhydrous K2c03 ( 2.2g15.6mmo 1) Dissolved inDMF(30ml) slowlydripping bromo Ethylacetate(2.2g13mmo 1)drippingis finished 0C stirring , 30min, then at 60C oil bath reaction 12h Thereaction liquid is poured into the ice waterfilter chloroform soluble solidsanhydrousNa2s04 drying, filtration, rotary dry solvent silica gel column chromatographyseparation , get yellow solid 2.31g , 2.31g (yield as 80%), will it,soluble Dioxane,[20ml]added sodium hydroxide solution [12ml] normalatmospheric temperature stir 2Hours Dioxane steameddry, The remaining liquid is poured intoice water. use dichloromethanewashing adjustingPHValue to 2 filter collect solid1.64g (yield as 79%), dissolve it in dichloromethane (30ml)addedN.N Diisopropylcarbodiimide(DIC)(1.06g8.41mmol) normal atmospherictemperature stirring 1 hour after added ,-4-Dimethylaminopyridine (DMAP0.17g1.39mmo l) Diethyl(hydroxymethyl)phosphonate 1.44g,8.57mmo I)Heating reflux 6 hours after usewith full water and edible salt washingreaction solutionanhydrous magnesium sulphate dry filtering after steam drying, Ethyl acetatepetroleum ether system recrystallization obtainedproduct -6-methoxy benzofurane,-2-carboxylic acid (2?_Diethylphosphonatemethyl ester products 2.48g (yield for 85%).
68%	With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 60℃; for 11h;	General procedure: To a mixture of 30 (2.09 g, 10 mmol) and anhydrous potassium carbonate (1.66 g, 12 mmol) in DMF at 0 C, ethyl thioglycolate (1.44 g, 12 mmol) was added dropwise. The system was stirred at 0 C for 1 h and then at 60 C for 10 h. The solution was filtered and concentrated under vacuum. The residue was then dissolved in chloroform (80 mL x 2), washed with water (160 mL x 3), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography over silica gel to afford the title compound (2.50 g, 95%) as a white solid
48%		A solution was prepared by adding 2-hydroxy-4-methoxybenzaldehyde (1 kg, 6.57 mol) to N,N-dimethylformamide (7 L). Molecular sieves 4 A (330 g) and potassium carbonate (2 kg, 14.47 mol) were added thereto, followed by stirring at room temperature (the color of the solution changed from red to orange when potassium carbonate was added). Ethyl bromoacetate (1.46 L, 13.14 mol) was slowly added to the resulting mixture, followed by further stirring for 30 minutes at room temperature. The reaction solution was further stirred by refluxing the solution for 1 hr at 175 C (white solid was formed). The completion of the reaction was observed by thin layer chromatography, and then the resulting solution was added with potassium carbonate (2 kg, 14.47 mol), stirred at reflux for 2 hrs. The reaction solution was cooled down to room temperature, and filtered to remove impurities. The filtrate was extracted with EtOAc and water, and the organic layer was separated, dried over Na2S04, and concentrated under reduced pressure. The resulting residue was solidified by diethyl ether, and filtered to obtain the title compound (684 g, 48%). NMR (DMSO-i/<5, 300 MHz) delta 7.66 (s, 1H), 7.64 (d, 1 H), 7.30 (d, 1 H), 6.97 (dd, 1H), 4.32 (q, 2H), 3.82 (s, 3H), 1.31 (t, 3H)

48%

With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 175℃; for 3.5h;Molecular sieve;

A solution was prepared by adding 2-hydroxy-4-methoxybenzaldehyde (1 kg, 6.57 mol) to N,N-dimethylformamide (7 L). Molecular sieves 4 A (330 g) and potassium carbonate (2 kg, 14.47 mol) were added thereto, followed by stirring at room temperature (the color of the solution changed from red to orange when potassium carbonate was added). Ethyl bromoacetate (1.46 L, 13.14 mol) was slowly added to the resulting mixture, followed by further stirring for 30 minutes at room temperature. The reaction solution was further stirred by refluxing the solution for 1 hr at 175 C. (white solid was formed). The completion of the reaction was observed by thin layer chromatography, and then the resulting solution was added with potassium carbonate (2 kg, 14.47 mol), stirred at reflux for 2 hrs. The reaction solution was cooled down to room temperature, and filtered to remove impurities. The filtrate was extracted with EtOAc and water, and the organic layer was separated, dried over Na2SO4, and concentrated under reduced pressure. The resulting residue was solidified by diethyl ether, and filtered to obtain the title compound (684 g, 48%). 1H NMR (DMSO-d6, 300 MHz) delta 7.66 (s, 1H), 7.64 (d, 111), 7.30 (d, 1H), 6.97 (dd, 1H), 4.32 (q, 2H), 3.82 (s, 3H), 1.31 (t, 3H)

Reference： [1]Patent: CN103130705,2016,B .Location in patent: Paragraph 0174-0176
[2]European Journal of Medicinal Chemistry,2015,vol. 96,p. 151 - 161
[3]Organic and Biomolecular Chemistry,2017,vol. 15,p. 1530 - 1536
[4]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 4939 - 4946
[5]Journal of Medicinal Chemistry,2017,vol. 60,p. 5472 - 5492
[6]Patent: WO2013/147568,2013,A1 .Location in patent: Page/Page column 12; 13
[7]Patent: US2015/65494,2015,A1 .Location in patent: Paragraph 0089; 0090; 0091
[8]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 5591 - 5593

20
[ 50551-57-0 ]
[ 208842-22-2 ]

Yield	Reaction Conditions	Operation in experiment
100%		<strong>[50551-57-0]6-methoxy-2-ethoxycarbonyl benzofuran</strong> (309 g, 1.403 mol) obtained from Step 1 above and sodium borohydride (159.2 g, 4.209 mol) were dissolved in THF (6.2 L), and stirred at reflux for 1 hr. MeOH (1.2 L) was slowly added over 3 hrs, and the resulting solution was stirred at reflux, followed by cooling to room temperature. Water (4.8 L) was added thereto, and the resulting solution was stirred for 1 hr at room temperature, followed by extraction with EtOAc. The organic layer was separated, dried over Na2S04, and concentrated under reduced pressure to obtain the title compound (250 g, 100%). NMR (CDC13, 300 MHz) delta 7.41 -7.38 (d, 1H), 6.99 (s, 1H), 6.87-6.83 (dd, 1H), 6.57 (s, 1H), 4.72 (s, 2H), 3.84 (s, 3H)
100%	With sodium tetrahydroborate; In tetrahydrofuran; for 1h;Reflux;	<strong>[50551-57-0]6-methoxy-2-ethoxycarbonyl benzofuran</strong> (309 g, 1.403 mol) obtained from Step 1 above and sodium borohydride (159.2 g, 4.209 mol) were dissolved in THF (6.2 L), and stirred at reflux for 1 hr. MeOH (1.2 L) was slowly added over 3 hrs, and the resulting solution was stirred at reflux, followed by cooling to room temperature. Water (4.8 L) was added thereto, and the resulting solution was stirred for 1 hr at room temperature, followed by extraction with EtOAc. The organic layer was separated, dried over Na2SO4, and concentrated under reduced pressure to obtain the title compound (250 g, 100%). 1H NMR (CDCl3, 300 MHz) delta 7.41-7.38 (d, 1H), 6.99 (s, 1H), 6.87-6.83 (dd, 1H), 6.57 (s, 1H), 4.72 (s, 2H), 3.84 (s, 3H)

Reference： [1]Patent: WO2013/147568,2013,A1 .Location in patent: Page/Page column 13
[2]Patent: US2015/65494,2015,A1 .Location in patent: Paragraph 0092; 0093; 0094
[3]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 5591 - 5593

21
[ 50551-57-0 ]
[ 53860-74-5 ]

Yield	Reaction Conditions	Operation in experiment
76%		To a stirred slurry LiAIH4 (0.1 14 g, 3 mmol) in anhydrous Et2O (5 ml) was added drop wise the solution of ethyl-<strong>[50551-57-0]6-methoxybenzofuran-2-carboxylate</strong> (0.380 g, 1 .73 mmol) and stirring was continued for 0.5 h at room temperature. The reaction mixture was quenched with EtOAc:H2O:MeOH mixture (7:3:1 ), diluted to 20 ml with EtOAc and filtered through Celite. The filtrate was evaporated and the residue was dried in vacuo to give the creamy paste (0.324 g) which was used as such for next step. This (0.310 g) was dissolved in anhydrous dioxane (10 ml) and MnO2 (1 g, excess) was added to it. The suspension was stirred at reflux for 3 h, cooled to room temperature and filtered through Celite pad. The filtrate was evaporated to dryness and the residue was purified by FCC (SiO2, hexane: EtOAc; 70:30), to give the title compound (0.182 g; 76%), as light pink crystalline solid. 1H-NMR (CDCI3) 3.87 (s, 3H); 6.96 (dd, 1 H, J = 2.22, 8.73 Hz); 7.03 (d, 1 H, J = 1.83 Hz); 7.48 (s, 1 H); 7.59 (d, 1 H, J = 8.7 Hz); 9.74 (s, 1 H

Reference： [1]Patent: WO2010/42998,2010,A1 .Location in patent: Page/Page column 67
[2]Organic and Biomolecular Chemistry,2017,vol. 15,p. 1530 - 1536

22
[ 111-39-7 ]
[ 50551-57-0 ]
[ 1254572-49-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 7085 - 7091

23
[ 50551-57-0 ]
[ 107-15-3 ]
[ 1254572-48-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 7085 - 7091

24
[ 50551-57-0 ]
[ 4152-09-4 ]
[ 1254572-50-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 7085 - 7091

25
[ 673-22-3 ]
[ 105-39-5 ]
[ 50551-57-0 ]

Reference： [1]Chinese Chemical Letters,2010,vol. 21,p. 1439 - 1442

26
[ 50551-57-0 ]
[ 1462470-22-9 ]

Reference： [1]Patent: WO2013/147568,2013,A1
[2]Patent: US2015/65494,2015,A1

27
[ 50551-57-0 ]
[ 1089681-42-4 ]

Reference： [1]Patent: WO2013/147568,2013,A1
[2]Patent: US2015/65494,2015,A1

28
[ 50551-57-0 ]
[ 1089681-44-6 ]

Reference： [1]Patent: WO2013/147568,2013,A1
[2]Patent: US2015/65494,2015,A1

29
[ 50551-57-0 ]
[ 1462469-84-6 ]

Reference： [1]Patent: WO2013/147568,2013,A1
[2]Patent: US2015/65494,2015,A1

30
[ 50551-57-0 ]
[ 1462470-44-5 ]

Reference： [1]Patent: WO2013/147568,2013,A1
[2]Patent: US2015/65494,2015,A1

31
[ 50551-57-0 ]
[ 1089682-48-3 ]

Reference： [1]Patent: WO2013/147568,2013,A1
[2]Patent: US2015/65494,2015,A1

32
[ 50551-57-0 ]
[ 1089681-69-5 ]

Reference： [1]Patent: WO2013/147568,2013,A1
[2]Patent: US2015/65494,2015,A1

33
[ 50551-57-0 ]
[ 1462470-08-1 ]

Reference： [1]Patent: WO2013/147568,2013,A1

34
[ 50551-57-0 ]
(E)-6-(2-(3-oxazolidinyl)ethoxy)-2-(4-dimethylaminostyryl)benzofuran hydrochloride [ No CAS ]

Reference： [1]Patent: US2015/65494,2015,A1

35
[ 50551-57-0 ]
1-(6-methoxybenzofuran-2-yl)-2-(methylsulfinyl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With sodium hydride; dimethyl sulfoxide; In tetrahydrofuran; mineral oil; at 0 - 30℃; for 0.5h;Inert atmosphere;	General procedure: Sodium hydride (60%, 2.4 g, 60 mmol) was washed three times with petroleum ether, dried under vacuum, and then mixed with dry dimethyl sulfoxide (25 mL). The system was protected with nitrogen and heated to 70-75 C for 1.5 h [38]. The reaction system was cooled to 0 C, and 36 (2.2 g, 10 mmol) in 20 mL of dry tetrahydrofuran was added slowly. The reaction system was then stirred for 0.5 h at 30 C and quenched with 200 mL of ice-cold water. The pH of the solution was adjusted to 3-4 with 2 N HCl. The mixture was extracted with chloroform (80 mL x 2), washed with water (160 mL x 3), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography over silica gel to afford the title compound (1.91 g, 76%) as a yellow solid

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 96,p. 151 - 161

36
[ 50551-57-0 ]
(diethoxyphosphoryl)methyl 6-methoxybenzofuran-2-carboxylate [ No CAS ]

Reference： [1]Patent: CN103130705,2016,B
[2]European Journal of Medicinal Chemistry,2020,vol. 200

37
[ 50551-57-0 ]
6-methoxy-benzofuran-2-carboxylic acid phosphonomethyl ester [ No CAS ]

Reference： [1]Patent: CN103130705,2016,B
[2]European Journal of Medicinal Chemistry,2020,vol. 200

38
[ 150-19-6 ]
[ 50551-57-0 ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 1530 - 1536

39
[ 50551-57-0 ]
(S)-1-(6-methoxybenzofuran-2-yl)-2-nitroethanol [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 1530 - 1536

40
[ 50551-57-0 ]
[ 334022-87-6 ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 5472 - 5492

41
[ 50551-57-0 ]
6-[2-(methylcarbamoyl)pyridin-4-yl]oxy}benzofuran-2-carboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 5472 - 5492

42
[ 50551-57-0 ]
ethyl 6-[2-(methylcarbamoyl)pyridin-4-yl]oxy}benzofuran-2-carboxylate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 5472 - 5492

43
[ 50551-57-0 ]
(R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 6-methoxybenzofuran-2-carboxylate [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2020,vol. 190

44
[ 673-22-3 ]
[ 50551-57-0 ]

Reference： [1]European Journal of Medicinal Chemistry,2020,vol. 190

45
[ 50551-57-0 ]
sodium (2-((6-methoxybenzofuran-2-carbonyl)oxy)ethyl)phosphonate [ No CAS ]