175278-30-5|4-Bromo-2-ethyl-1-iodobenzene| Ambeed

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Quality Control of [ 175278-30-5 ] Purity: 98% SDS Specification

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Product Details of [ 175278-30-5 ]

CAS No. :	175278-30-5
Formula :	C₈H₈BrI
M.W :	310.96
SMILES Code :	IC1=CC=C(Br)C=C1CC
MDL No. :	MFCD00221458
InChI Key :	JWKQXPHYKRQLEJ-UHFFFAOYSA-N
Pubchem ID :	2761396

Safety of [ 175278-30-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 175278-30-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.25
Num. rotatable bonds	1
Num. H-bond acceptors	0.0
Num. H-bond donors	0.0
Molar Refractivity	56.63
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	0.0 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.74
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	4.06
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.62
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.	4.53
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	4.26
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.	-4.7
Solubility	0.00615 mg/ml ; 0.0000198 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.	-3.76
Solubility	0.0535 mg/ml ; 0.000172 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	-4.97
Solubility	0.00329 mg/ml ; 0.0000106 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	Low
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	No
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	No
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	Yes
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	Yes
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.	-5.31 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	1.0
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	1.0 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<1.0
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)	1.92

Application In Synthesis of [ 175278-30-5 ]

* 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 [ 175278-30-5 ]

[ 175278-30-5 ] Synthesis Path-Downstream 1~35

1
[ 121-43-7 ]
[ 175278-30-5 ]
[ 1046861-62-4 ]

Yield	Reaction Conditions	Operation in experiment
		Step 2: Preparation of 4-bromo-2-ethylphenylboronic acidTo a solution of <strong>[175278-30-5]4-bromo-2-ethyl-1-iodobenzene</strong> (80 g, 0.25 mol) in tetrahydrofuran (800 ml) at - 75 0C is added n-butyl lithium (1.6 M in hexanes, 188 ml, 0.3 mol) dropwise maintaining the temperature of the reaction mixture below -70 °C. When the addition is complete the mixture is stirred at -75 0C for an additional 30 minutes and then trimethyl borate (153.7 g, 1.48 mol) is added dropwise. After the addition is complete the reaction is stirred at -75 0C for 1 hour, then allowed to come to room temperature and stirred for 2 hours, followed by cooling in an ice bath and acidification with 0.5 N aqueous hydrochloric acid. The mixture is extracted with ethyl acetate (3 x 500 ml) and the organic fractions are combined, washed with brine, then dried over anhydrous sodium sulphate. The mixture is filtered and the filtrate is evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give 4-bromo-2- ethylphenylboronic acid (26 g) as a white solid.

References: [1]Patent: WO2009/74314,2009,A1 .Location in patent: Page/Page column 165.

2
[ 121-43-7 ]
[ 175278-30-5 ]
[ 1160561-22-7 ]

Yield	Reaction Conditions	Operation in experiment
		Step 2: Preparation of 4-bromo-2,6-diethylphenylboronic acidTo a solution of 4-bromo-2,6-diethyl-1-iodobenzene (1O g, 0.029 mol) in tetrahydrofuran (100 ml) at -75 °C is added n-butyl lithium (1.6 M in hexanes, 22.2 ml, 0.035 mol) dropwise maintaining the temperature of the reaction mixture below -70 0C. When the addition is complete the mixture is stirred at -75 °C for an additional 30 minutes and then trimethyl borate (17.98 g, 0.17 mol) is added dropwise. After the addition is complete the reaction is stirred at -75 0C for 1 hour, then allowed to come to room temperature and stirred for 2 hours, followed by cooling in an ice bath and acidification with 0.5 N aqueous hydrochloric acid. The mixture is extracted with ethyl acetate (3 x 300 ml) and the organic fractions are combined, washed with brine, dried over anhydrous sodium sulphate. The mixture is filtered and the filtrate is evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give 4-bromo-2,6- diethylphenylboronic acid ( 5 g) as a white solid.

References: [1]Patent: WO2009/74314,2009,A1 .Location in patent: Page/Page column 167.

3
[ 175278-30-5 ]
[ 68-12-2 ]
[ 1114808-89-7 ]

Yield	Reaction Conditions	Operation in experiment
86%	With isopropylmagnesium chloride; In tetrahydrofuran; at -15 - 25℃; for 3h;Inert atmosphere;	full text is not avalable from article
		Example R: Preparation of 4-bromo-2-ethylbenzaldehydeTo a solution of <strong>[175278-30-5]4-bromo-2-ethyl-1-iodobenzene</strong> (75 g, 0.24 mol) in tetrahydrofuran (375 ml) at - 75 0C is added n-butyl lithium (1.6 M in hexanes, 196 ml, 0.31 mol) dropwise, maintaining the temperature of the reaction mixture below -70 °C. When the addition is complete the mixture is stirred at -75 0C for an additional 30 minutes and then lambda/,lambda/-dimethylformamide (70.7 g, 0.97 mol) is added dropwise. After the addition is complete the reaction is stirred at -75 °C for 2 hours, then allowed to warm to room temperature for 2 hours. The mixture is cooled in an ice bath and acidified with 0.5 N aqueous hydrochloric acid. The mixture is extracted with ethyl acetate (3 x 500 ml) and the organic fractions are combined, washed with brine, and dried over anhydrous sodium sulphate. The mixture is filtered and the filtrate is evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give 4-bromo-2- ethylbenzaldehyde (48 g) as an oil.

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2016,vol. 55B,p. 854 - 881.
[2]Patent: WO2009/74314,2009,A1 .Location in patent: Page/Page column 170.

4
[ 45762-41-2 ]
[ 175278-30-5 ]

Yield	Reaction Conditions	Operation in experiment
		Step 1: Preparation of 4-bromo-2-ethyl-1-iodobenzene <n="166"/>To a stirred mixture of 4-bromo-2-ethylaniline (80 g, 0.4 mol) in distilled water (400 ml) is added concentrated sulphuric acid (80 ml), followed by brief heating to 60 0C for 1 hour until dissolution is complete. The mixture is allowed to cool to room temperature then further cooled to approximately 0 0C in an ice/salt bath. To this slurry is added an aqueous solution of sodium nitrite (28 g, 0.4 mol) in distilled water (140 ml) dropwise over 15 minutes, maintaining the temperature below 5 0C, followed by additional stirring for 30 minutes. The reaction mixture is allowed to come to room temperature and then a solution of aqueous potassium iodide (199 g, 1.2 mol) in distilled water (200 ml) is added dropwise at room temperature. After the addition is complete the solution is briefly heated to 80 0C then allowed to cool to room temperature again. The reaction mixture is extracted with ethyl acetate (1000 ml x 3) and the organic phase is washed with 1M aqueous hydrochloric acid (500 ml) and aqueous sodium thiosulfate (2 x 250 ml). The organic phase is dried over anhydrous sodium sulphate, filtered and the filtrate is concentrated under reduced pressure. The residue is purified by column chromatography on silica gel to give 4-bromo-2-ethyl-1-iodobenzene (84.6 g) as an orange liquid.

References: [1]Patent: WO2009/74314,2009,A1 .Location in patent: Page/Page column 164-165.
[2]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 3766 - 3773.

5
[ 98-01-1 ]
[ 175278-30-5 ]
[ 1237529-61-1 ]

Yield	Reaction Conditions	Operation in experiment
		Example 6 : Preparation of 2-r4-(4-chlorophenoxy)-2-ethylphenyl1cvclopentane-1 ,3-dioneStep 1 : Preparation of (4-bromo-2-ethylphenyl)furan-2-yl methanolMagnesium turnings (1.16g, 0.048mol) are stirred under a nitrogen atmopsphere for 30 minutes, followed by dropwise addition of <strong>[175278-30-5]4-bromo-2-ethyl-1-iodobenzene</strong> (15.Og, 0.048mol) as a solution in anhydrous tetrahydrofuran (40ml), until the magnesium is just covered. A crystal of iodine is added and the reaction heated to reflux. After initiation begins external heating is stopped and the remaining aryl halide solution is added at such a rate as to maintain a controlled reflux. Once addition is complete the reaction is heated at reflux for 1 hour and the mixture is then cooled to room temperature. A solution of furan-2-carbaldehyde (4.0ml, 0.048mol) in anhydrous tetrahydrofuran (10ml) is then added dropwise, and the suspension is then stirred at room temperature for 20 hours. The reaction is quenched with saturated ammonium chloride (200ml) and extracted with ethyl acetate (200ml). The organic phase is separated, dried over anhydrous magnesium sulfate then evaporated under reduced pressure. The crude product is purified by flash column chromatography (1 :4 ethyl acetate/hexane eluant) to afford (4-bromo-2-ethyl- phenyl)furan-2-yl methanol as a brown oil.

References: [1]Patent: WO2010/89210,2010,A1 .Location in patent: Page/Page column 66.

6
[ 98-01-1 ]
[ 175278-30-5 ]
[ 1112412-95-9 ]

Yield	Reaction Conditions	Operation in experiment
		4-Bromo-2-iodoethyl benzene (50.0 g, 160.8 mmol) is dissolved in anhydrous tetrahydrofuran (250 ml) and cooled to -7O0C under an atmosphere of nitrogen, lsopropylmagnesium chloride (2M solution in THF, 100 ml, 200 mmol) is added dropwise with vigorous stirring over 40 minutes, maintaining the internal temp below -6O0C by external cooling. When the addition is complete, the reaction is stirred at -7O0C for 20 minutes then allowed to warm to room temperature over 1 h 20 minutes. The reaction mixture is then cooled to -7O0C and a solution of 2-furaldehyde (16 ml, 18.6 g, 190 mmol) in tetrahydrofuran (50 ml) is added dropwise over 40 minutes. On completion of the addition, the reaction is allowed to warm to room temperature and stirred at room temperature for 3 hours. Saturated aqueous ammonium chloride solution (-500 ml) is added and the mixture is extracted into ethyl acetate. The organic solutions are combined, washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue is further purified by column chromatography on silica gel to give (5-bromo-2- ethylphenyl)furan-2-ylmethanol (40.7 g).

References: [1]Patent: WO2010/102848,2010,A1 .Location in patent: Page/Page column 54-55.

7
[ 175278-30-5 ]
[ 7390-62-7 ]
[ 1360066-70-1 ]

Yield	Reaction Conditions	Operation in experiment
49%	With copper(l) iodide; tetrabutylammomium bromide; sodium t-butanolate; In N,N-dimethyl-formamide; at 150℃; for 1.5h;Sealed tube; Microwave irradiation;	General procedure: In a conical-bottomed microwave vial, the mixture of 8 mercaptoadenine (0.1 mmol), respective aryl iodide (0.1 mmol), Cul (0.02 mmol), NaO?-Bu (0.3 mmol) and ?-butyl ammonium bromide (0.02 mmol) in DMF (2 mL) was charged. The sealed vial was irradiated in the microwave for 1.5 h at 150 °C. After cooling, the reaction mixture was condensed under reduced pressure and purified by flash chromatography (CH2Cl2:MeOH:AcOH, 20: 1 :0.5). [0216] 8-((4-Bromo-2-ethylphenyl)thio)-9H-purin-6-amine (2a). Obtained by method B as a light yellow solid in 49 percent yield. MS (ESI): m/z 351.8 [M + H]+.

References: [1]Synlett,2011,p. 3008 - 3012.
[2]Patent: WO2015/23976,2015,A2 .Location in patent: Paragraph 0215-0216.

8
[ 175278-30-5 ]
[ 1408285-51-7 ]
[ 1452670-53-9 ]

References: [1]Organic Letters,2013,vol. 15,p. 4666 - 4669.

9
[ 175278-30-5 ]
[ 202522-04-1 ]

References: [1]Patent: WO2013/149997,2013,A1 .
[2]Patent: WO2013/149997,2013,A1 .
[3]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2016,vol. 55B,p. 854 - 881.
[4]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2016,vol. 55B,p. 854 - 881.
[5]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2016,vol. 55B,p. 854 - 881.
[6]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2016,vol. 55B,p. 854 - 881.

10
[ 175278-30-5 ]
[ 1187028-46-1 ]

11
[ 4394-85-8 ]
[ 175278-30-5 ]
[ 1114808-89-7 ]

Yield	Reaction Conditions	Operation in experiment
62%		Method 1 : To a solution of <strong>[175278-30-5]4-bromo-2-ethyliodobenzene</strong> (1 .61 mmol, 0.5 g) dissolved in anhydride THF (6 mL) at -785C was added 2.5 M n-butyllithium solution in hexane (1 .9 mmol, 0.77 mL) dropwise. The mixture was stirred 30 min at -78 5C before /V-formylmorpholine (3.69 mmol, 0.37 mL) was added and the reaction stirred at this temperature for 1 h. The reaction was quenched with aqueous 1 N HCI and extracted with EtAcO. The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. Purification of the crude material by flash chromatography on silica gel using an elution of 3percent ethylacetate in hexanes afforded the title compound (21 1 mg, 62percent). 1 H (400 MHz, CDCI3) delta 10.24 (1 H, s), 7.69 (1 H, d, J = 8.4 Hz), 7.51 (1 H, dd, J = 8.4 & 2 Hz), 7.48 (1 H, d, J = 2 Hz), 3.05 (2H, q, J = 7.6 Hz), 1 .28 (3H, t, J = 7.6 Hz). LC-MS: tR = 3.67 [M+H]+= 213/215 (method 3)
62%		full text is not avalable from article

References: [1]Patent: WO2013/149997,2013,A1 .Location in patent: Page/Page column 51.
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2016,vol. 55B,p. 854 - 881.

12
[ 175278-30-5 ]
[ 7390-62-7 ]
C₁₈H₁₈BrN₅S [ No CAS ]
8-((4-bromo-2-ethylphenyl)thio)-9-(pent-4-yn-1-yl)-9H-purin-6-amine [ No CAS ]

References: [1]Patent: WO2015/23976,2015,A2 .

Yield	Reaction Conditions	Operation in experiment
4 g		General procedure: Step-1 :- Preparation of 3-chloro-4-iodobenzonitrile A mixture of 4-amino-3-chlorobenzonitrile (3.0 g, 19.66 mmol), /?-toluenesulfonic acid (11.20 g, 55.98 mmol) in acetonitrile (30 mL) was stirred at RT for 4 h. To this mixture, aq. solution of NaN02 (2.03 g, 29.49 mmol in 7 mL water) and KI (4.89 g, 29.49 mmol) was added at 0°C and stirred further for 1 h. After the reaction completion, the reaction mixture was quenched with water, washed with an aqueous solution of NaHS03 and extracted with EtOAc. The organic layer was washed with water, brine, dried over Na2S04 and concentrated to afford 4.0 g of the title product. 1H NMR (300 MHz, CDClj ): delta 8.02-7.99 (d, = 8.4 Hz, 1H), 7.71 (s, 1H), 7.23-7.21 (d, = 8.1 Hz, 1H).

14
[ 175278-30-5 ]
C₃₁H₃₇BO₇ [ No CAS ]
C₃₃H₃₃BrO₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
6 g	With tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene;Inert atmosphere; Reflux;	6c: 50 of distilled water and 25 of ethanol are added to 6b solution (9.00 g, 15.0 mmol) in 100 toluene and4- bromo -2- ethyl iodobenzene (4.98 g, 16.0 mmol). Potassium carbonate (4.24g, 40.0 mmol) is subsequently added. The generated suspension is carefully degassedwith argon. Thereafter, tetrakis (trip henylphosphine) palladium (0) (0.66 g,0.57 mmol) is added. The reaction mixture is heated up under reflux and it isstirred overnight. After the reaction mixture is cooled at room temperature, itis carefully neutralized to become pH7 with 6 M HCl acid. The aqueous phase wasextracted in the ethyl acetate. The organic phase is added and it is washed by saturationaqueous solution of NaCl and it is dried on the sodium sulfate. After thesolvent is removed in vacuum, it is refined by a column chromatography using heptane / ethyl acetate (6:1) as aneluent to provide 6c as yellow oil (6.0 g).

References: [1]Patent: KR2016/15166,2016,A .Location in patent: Paragraph 1522-1526.

15
[ 175278-30-5 ]
(rac)-3-ethyl-4-((3aS,4S,9bR)-3a,4,5,9b-tetrahydro-8-methyl-3H-cyclopenta[c]quinolin-4-yl)benzoic acid [ No CAS ]
(rac)-3-ethyl-4-((3aS,4R,9bR)-3a,4,5,9b-tetrahydro-8-methyl-3H-cyclopenta[c]quinolin-4-yl)benzoic acid [ No CAS ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2016,vol. 55B,p. 854 - 881.
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2016,vol. 55B,p. 854 - 881.
[3]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2016,vol. 55B,p. 854 - 881.
[4]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2016,vol. 55B,p. 854 - 881.

16
[ 175278-30-5 ]
3-ethyl-4-(8-methoxy-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinolin-4-yl)benzoic acid [ No CAS ]
3-ethyl-4-(8-methoxy-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinolin-4-yl)benzoic acid [ No CAS ]

17
[ 175278-30-5 ]
C₃₄H₄₂O [ No CAS ]

References: [1]Patent: JP2017/25007,2017,A .

18
[ 175278-30-5 ]
C₃₄H₄₄O [ No CAS ]

References: [1]Patent: JP2017/25007,2017,A .

19
[ 175278-30-5 ]
C₂₆H₃₄O [ No CAS ]

References: [1]Patent: JP2017/25007,2017,A .
[2]Patent: CN107108457,2017,A .

20
[ 175278-30-5 ]
C₂₆H₃₆O [ No CAS ]

References: [1]Patent: JP2017/25007,2017,A .

21
[ 175278-30-5 ]
C₂₅H₃₅BO₂ [ No CAS ]

References: [1]Patent: JP2017/25007,2017,A .

22
[ 175278-30-5 ]
C₃₆H₄₆O₂ [ No CAS ]

References: [1]Patent: JP2017/25007,2017,A .

23
[ 175278-30-5 ]
[ 136321-96-5 ]
C₂₅H₃₃Br [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; potassium carbonate; In water; isopropyl alcohol; toluene; at 80℃; for 6h;	The compound (T-90) (21.1 g), tetrakistriphenylphosphine palladium (0.74 g), potassium carbonate (17.7 g), tetrabutylammonium bromideBromo-2-ethyl-1-iodobenzene (20.0 g),Toluene (200 ml), IPA (150 ml) and H2O (50 ml) were placed in the reactor and stirred at 80 ° C for 6 hours.After the insolubles were removed, the reaction mixture was poured into water and the aqueous layer was extracted with toluene.The organic layer formed simultaneously with water washing was dried over anhydrous magnesium sulfate.The solution was concentrated under reduced pressure and the residue was purified by silica gel chromatography (volume ratio, heptane: toluene = 4: 1) to obtain compound (T-91) (22.6 g; 85percent).
80%	With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; potassium carbonate; In water; isopropyl alcohol; toluene; at 90℃; for 5h;	Compound (T-1) (10.0 g), <strong>[175278-30-5]4-bromo-2-ethyl-1-iodobenzene</strong> (13.6 g), Tetrakis (triphenylphosphine) palladium(2.1 g), potassium carbonate (10.1 g), tetrabutylammonium bromide (1.18 g) and toluene (300 ml), IPA (80 ml) and pure water (20 ml) were charged into a reactor And the mixture was stirred at 90 ° C. for 5 hours. The reaction mixture was poured into water and the aqueous layer was extracted with toluene. The combined organic layers were washed with brine and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, heptane: toluene = 4: 1). (T-2) (12.6 g; 80percent) was obtained by further recrystallization from a mixed solvent of heptane and toluene (volume ratio, 4: 1).

References: [1]Patent: CN107108457,2017,A .Location in patent: Paragraph 0790; 0792; 0793.
[2]Patent: JP2017/25007,2017,A .Location in patent: Paragraph 0160-0161.

24
[ 175278-30-5 ]
[ 943741-74-0 ]