50548-45-3|1-Bromodibenzo[b,d]furan| Ambeed

Structure of 50548-45-3

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Quality Control of [ 50548-45-3 ] Purity: 97% SDS Specification

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Product Details of [ 50548-45-3 ]

CAS No. :	50548-45-3
Formula :	C₁₂H₇BrO
M.W :	247.09
SMILES Code :	BrC1=C2C(OC3=CC=CC=C23)=CC=C1
MDL No. :	MFCD00094238
InChI Key :	WUYYVOWEBMOELQ-UHFFFAOYSA-N
Pubchem ID :	190542

Safety of [ 50548-45-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 50548-45-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	13
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	61.42
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	13.14 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.66
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	4.57
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	4.35
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	3.5
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	4.12
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.84

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.94
Solubility	0.00285 mg/ml ; 0.0000115 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-4.57
Solubility	0.00666 mg/ml ; 0.000027 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-5.82
Solubility	0.000374 mg/ml ; 0.00000151 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	Yes
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	Yes
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-4.56 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<2.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.72

Application In Synthesis of [ 50548-45-3 ]

* 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.

Downstream synthetic route of [ 50548-45-3 ]

[ 50548-45-3 ] Synthesis Path-Downstream 1~35

1
[ 50548-45-3 ]
[ 50548-40-8 ]

References: [1]Journal of the American Chemical Society,1939,vol. 61,p. 1365,1369.

2
[ 50548-45-3 ]
[ 54470-37-0 ]

References: [1]Journal of the American Chemical Society,1939,vol. 61,p. 1365,1369.

3
[ 50548-45-3 ]
[ 42747-98-8 ]

References: [1]Journal of the American Chemical Society,1939,vol. 61,p. 1365,1369.

4
[ 667937-51-1 ]
[ 50548-45-3 ]

References: [1]Journal of the American Chemical Society,1954,vol. 76,p. 5783,5784.

5
[ 50548-39-5 ]
[ 50548-45-3 ]

References: [1]Journal of the American Chemical Society,1939,vol. 61,p. 1365,1369.

Yield	Reaction Conditions	Operation in experiment
95%	With sodium hydride; In N,N-dimethyl-formamide; at 0 - 100℃; for 1.33333h;	General procedure: Compound A-2 (40.0 g, 132.7 mmol) was dissolved in distilled dimethylformamide (400 mL). It cooled to 0 ,Sodium hydride (3.5 g, 145.9 mmol) was slowly added dropwise thereto. The mixture was stirred for 20 minutes and then at 100 ° C for 1 hour. After completion of the reaction, the reaction mixture was cooled to room temperature,Ethanol (100 mL) was slowly added.The mixture was distilled under reduced pressure, and the resulting mixture was extracted with chloroform,And recrystallized from ethyl acetate to obtain Compound A-3 (30.3 g, yield 81percent).
95%	With sodium hydride; In N,N-dimethyl-formamide; at 0 - 100℃; for 1.3h;	General procedure: Compound A-2 (40.0 g, 132.7 mmol) was dissolved in distilled dimethylformamide (400 mL)Respectively. It cooled to 0 , sodium hydride here(3.5 g, 145.9 mmol) was slowly added dropwise.Stir for 20 minutes and then stir at 100 for 1 hour. After the reaction was completed, the reaction mixture was cooled to room temperature, and ethanol (100 mL) was slowly added thereto. The mixture was vacuum distilled, and the resulting mixture was recrystallized from chloroform and ethyl acetate to obtain Compound A-3 (30.3 g, yield 81percent)It was obtained.

7
2,3-diethynylbenzo[b]furan [ No CAS ]
[ 50548-45-3 ]

References: [1]Journal of Organic Chemistry,2005,vol. 70,p. 10482 - 10487.

8
[ 3693-22-9 ]
[ 50548-45-3 ]

References: [1]Journal of the American Chemical Society,1954,vol. 76,p. 5783,5784.

9
[ 50548-45-3 ]
[ 93533-84-7 ]

References: [1]Journal of the American Chemical Society,1939,vol. 61,p. 1365,1369.

10
[ 50548-45-3 ]
[ 107624-55-5 ]

References: [1]Journal of the American Chemical Society,1939,vol. 61,p. 1365,1369.

11
[ 50548-43-1 ]
[ 50548-45-3 ]

References: [1]Journal of the American Chemical Society,1939,vol. 61,p. 1365,1369.

12
dibenzofuran-4-carboxylic acid amide [ No CAS ]
[ 50548-45-3 ]

References: [1]Journal of the American Chemical Society,1939,vol. 61,p. 1365,1369.

13
[ 50548-37-3 ]
[ 50548-45-3 ]

References: [1]Journal of the American Chemical Society,1939,vol. 61,p. 1365,1369.
[2]Patent: JP2018/90561,2018,A .

14
[ 50548-38-4 ]
[ 50548-45-3 ]

References: [1]Journal of the American Chemical Society,1939,vol. 61,p. 1365,1369.
[2]Patent: JP2018/90561,2018,A .

15
[ 50548-45-3 ]
[ 73183-34-3 ]
2-(dibenzo[b,d]furan-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; for 24h;Reflux;	31.3 g (126.7 mM) of <strong>[50548-45-3]1-bromodibenzo[b,d]furan</strong>, (<strong>[50548-45-3]1-bromodibenzo[b,d]furan</strong>),190.0 g (190.0 mM) bis (pinacolato) diboron, 4.6 g (6.3 mM) PdCl2(dppf) 37.3 g (380.1 mM) of KOAc was dissolved in 300 mL of 1,4-dioxane and refluxed for 24 hours. After the reaction was completed, distilled water and DCM (dichloromethane) were added at room temperature. The organic layer was dried with MgSO 4 and the solvent was removed by a rotary evaporator. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized from methanol to obtain the desired compound 1-5-3 37 g (quant.).
98%	With palladium diacetate; calcium acetate; In N,N-dimethyl-formamide; at 80℃;Inert atmosphere;	101g (410 mmol) of <strong>[50548-45-3]1-bromodibenzofuran</strong> was added to 500 ml flask under protectivegas, 273 g (1055 mmol) of bis (pinacolato) diborane (CAS 73183-34-3) wasdissolved in in 1500 ml dry DMF and degassed for 30 minutes. 121 g (1229 mmol) Calciumacetate and 8.4 g (37 mmol) palladium acetate are added subsequently, and thebatch was heated overnight at 80C . When the reaction was complete, themixture was diluted with 300 ml of toluene, and extracted with water. Thesolvent was removed in rotary evaporator, and the product was thenrecrystallized from heptane. Yield: 118 g (401mmol), 98% theory.
70%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; for 10h;Reflux;	500ml round bottom flask reactor, <strong>[50548-45-3]1-bromodibenzofuran</strong>(20.0g, 0.081mmol), bis(pinacolato)diboron (26.7g, 0.105mol), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (1.3g, 0.002mol), potassium acetate (19.9g, 0.202mol), into a 1,4-dioxane 200ml were stirred for 10 hours under reflux after completion of the reaction was filtered a pad of celite. Filtrate was concentrated under a reduced pressure was separated and then the column was recrystallized from dichloromethane and heptane to give a intermediate 4-a> (17.0g, 70%).

70%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; for 10h;Reflux;	500ml round bottom flask reactor1-Bromo-dibenzofuran (20.0g, 0.081mmol), Bis (pinacolato) diboron (26.7g, 0.105mol),[1,1'-bis (diphenylphosphino) ferrocene] palladium in a Dijk (1.3g, 0.002mol),Potassium acetate (19.9g,0.202mol), into a 1,4-dioxane 200ml were stirred for 10 hours under reflux. After the completion of the reaction was filtered a pad of Celite. femaleAfter concentration under reduced pressure they were separated by liquid column and recrystallized with dichloromethane-heptane to give a (17.0g, 70%).
70%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; for 10h;Reflux;	<strong>[50548-45-3]1-bromodibenzofuran</strong> (20.0 g, 0.081 mmol) was charged in a 500 ml round bottom flask reactor,Bis (pinacol) diboron (26.7 g, 0.105 mol)[1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (1.3 g, 0.002 mol)Potassium acetate (19.9 g, 0.202 mol), 200 ml of 1,4-dioxane and stirred under reflux for 10 hours.After the reaction was complete, the diatomaceous earth liner was filtered. The filtrate was concentrated under reduced pressure and then separated by column,And recrystallized from dichloromethane and heptane to obtain (17.0 g, 70%).
70%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; for 1h;Reflux;	In a 500-mL round-bottom flask reactor, <strong>[50548-45-3]1-bromodibenzofuran</strong> (20.0 g, 0.081 mmol), bis(pinacolato)diboron (26.7 g, 0.105 mol), [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium (1.3 g, 0.002 mol), potassium acetate (19.9 g, 0.202 mol), and 1,4-dioxane (200 ml) were stirred together for hrs under reflux. After completion of the reaction, filtration was performed through a celite pad. The filtrate was concentrated in a vacuum, purified by column chromatography, and recrystallized in dichloromethane and heptane to afford <Intermediate 4-a> (17.0 g, 70%).
70%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; for 10h;Reflux;	In a 500-mL round-bottom flask reactor, <strong>[50548-45-3]1-bromodibenzofuran</strong> (20.0 g, 81 mmol), bis(pinacolato)diboron (26.7 g, 105 mmol), [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium (1.3 g, 0.002 mol), potassium acetate (19.9 g, 202 mmol), and 1,4-dioxane (200 ml) were stirred together for 10 hrs under reflux. Concentration in a vacuum was followed by column chromatographic purification. Recrystallization in dichloromethane and heptane afforded (17.0 g, 70%).
70%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; for 10h;Reflux;	Intermediate 8-a was synthesized according to Scheme 60 below:<strong>[50548-45-3]1-bromodibenzofuran</strong> (20.0g, 0.081mmol), bis (pinacolato) diboron (26.7g, 0.105mol) in 500ml round bottom flask reactor,200 ml of [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (1.3 g, 0.002 mol), potassium acetate (19.9 g, 0.202 mol) and 1,4-dioxane were added and stirred under reflux for 10 hours. . After the reaction was completed, the celite pad was filtered. The filtrate was concentrated under reduced pressure and column separatedRecrystallization from dichloromethane and heptane gave

References: [1]Patent: KR101959821,2019,B1 .Location in patent: Paragraph 0280-0283.
[2]Patent: KR2016/28524,2016,A .Location in patent: Paragraph 0254-0256.
[3]Patent: KR2015/130206,2015,A .Location in patent: Paragraph 0561-0567.
[4]Patent: KR2016/13678,2016,A .Location in patent: Paragraph 0591-0597.
[5]Patent: CN107207454,2017,A .Location in patent: Paragraph 0306; 0307; 0308; 0310; 0311.
[6]Patent: US2018/233669,2018,A1 .Location in patent: Paragraph 0213-0217.
[7]Patent: US2018/319776,2018,A1 .Location in patent: Paragraph 0171-0172.
[8]Patent: KR2019/111856,2019,A .Location in patent: Paragraph 0591-0597.

16
[ 50548-45-3 ]
C₂₀H₁₃BrO₃ [ No CAS ]

References: [1]Patent: KR2015/130206,2015,A .

17
[ 50548-45-3 ]
[ 5419-55-6 ]
[ 7732-18-5 ]
dibenzo[b,d]furan-1-yl-boronic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%		Sub 1-4-1 (4.94, 20mmol) was dissolved in anhydrous ether, lowering the temperature of the reaction to -78 °C, and dropwise addition of n-BuLi (2.5M in hexane) (1.4g, 22mmol) slowly, and after the reaction was stirred for 30 minutes. After lowering the temperature of the reaction back to -78 °C and dropwise added triisopropylborate (5.6g, 30mmol). Stirring at room temperature, diluted with water and it binds the 2N HCl. After the reaction was completed, the organic layer was dried and extracted with water and ethyl acetate with MgSO4 and concentrated and to the resulting organics silicagel column and recrystallized to obtain 3.14g of Sub 1(33) (yield: 74percent).
72.8%		Into a 1 L four-necked round bottom flask equipped with a stirrer, a Liebig condenser fitted with a calcium chloride tube, a nitrogen inlet tube, a 200 mL isobaric dropping funnel and a thermometer, 34.5 g of the bromide obtained in the above (139.6 mmol) of dehydrated THF and 325 mL of dehydrated THF, and the mixture was cooled to -60 ° C. or lower in an acetone-dry ice bath under a nitrogen stream. Subsequently, 106 mL (167.6 mmol) of n-BuLi was added dropwise at -50 ° C. or lower, then the isobaric dropping funnel was washed with 100 mL of THF and added to the reaction solution. Subsequently, after postreaction at -50 ° C. or lower for 1 hour, 43 mL (181.6 mmol) of [B (i-PrO) 3] was added dropwise at -45 ° C. or lower. Subsequently, the isobaric dropping funnel was washed with 80 mL of THF and added to the reaction solution, followed by stirring at -45 ° C. or lower for 30 minutes. The acetone-dry ice bath was removed, the temperature was returned to room temperature, and the reaction was continued for additional 20 hours to obtain boron To obtain a reaction solution.Next, 24 mL of concentrated hydrochloric acid and 241 mL of water were placed in a 1 L four-necked round bottom flask equipped with a stirring device, a Liebig condenser (not required), a 1 L dropping funnel and a thermometer, ° C. Subsequently, the boron reaction solution was dropped at a temperature not exceeding 10 ° C., and the mixture was stirred at 10 ° C. or less for 1 hour, then returned to room temperature and stirred for 3 hours.The obtained reaction solution was transferred to a 1 L separating funnel, the organic layer was separated, and the aqueous layer was extracted with 340 mL of ethyl acetate. Next, the organic layers were combined and washed with saturated brine 240 mL, dried over magnesium sulfate, magnesium sulfate was removed by suction filtration, and the solvent was distilled off under reduced pressure. Subsequently, 220 mL of n-heptane was added to the obtained crude crystals, rinsed at 50 ° C. for 1 hour, cooled to room temperature and filtered by suction to obtain 21.6 g of the desired boronic acid (yield 72.8percent)

References: [1]Patent: KR2015/121337,2015,A .Location in patent: Paragraph 0115; 0116; 0117; 0118.
[2]Patent: JP2018/90561,2018,A .Location in patent: Paragraph 0079.

18
[ 50548-45-3 ]
C₄₂H₂₃N₃O [ No CAS ]