129540-24-5|2-(2-Bromophenyl)pyrrolidine| Ambeed

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Quality Control of [ 129540-24-5 ] Purity: 97% SDS Specification

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Product Details of [ 129540-24-5 ]

CAS No. :	129540-24-5
Formula :	C₁₀H₁₂BrN
M.W :	226.11
SMILES Code :	BrC1=CC=CC=C1C2NCCC2
MDL No. :	MFCD02663433
InChI Key :	BSLGMIVYENBFFY-UHFFFAOYSA-N
Pubchem ID :	3299348

Safety of [ 129540-24-5 ]

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

Computational Chemistry of [ 129540-24-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.4
Num. rotatable bonds	1
Num. H-bond acceptors	1.0
Num. H-bond donors	1.0
Molar Refractivity	58.13
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	12.03 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.53
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	2.5
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.17
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.	2.8
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	3.18
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.64

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.12
Solubility	0.171 mg/ml ; 0.000757 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.4
Solubility	0.904 mg/ml ; 0.004 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	-4.19
Solubility	0.0147 mg/ml ; 0.000065 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	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	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	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.	-5.9 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<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)	1.97

Application In Synthesis of [ 129540-24-5 ]

* 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 [ 129540-24-5 ]

[ 129540-24-5 ] Synthesis Path-Downstream 1~35

1
[ 129540-26-7 ]
[ 129540-24-5 ]

Yield	Reaction Conditions	Operation in experiment
		Compound 10 2(2-Bromophenyl)pyrrolidine 5-(2-Bromophenyl)-3,4-dihydro-2H-pyrrole (compound 8; 393 mmol, 88 g) was dissolved in methanol (1300 mL), then the acetic acid (330 mL) was added and the solution cooled to -65 C. under a nitrogen atmosphere. Sodium borohydride (589 mmol, 22.28 g) was added portionwise over 1 hour. The reaction was stirred at -65 C. for 30 minutes, then the cooling bath was removed and the reaction mixture temperature was allowed to rise to room temperature. The bulk of the methanol was removed under vacuum then 5N HCl (950 mL) was added and the solution extracted with ether (2×500 mL). The aqueous solution was then basified with sodium hydroxide pellets (310 g) with ice-bath cooling, maintaining the reaction temperature less than 30 C. The basified aqueous was then extracted with ethyl acetate (3×800 mL), the combined organics washed with brine (800 mL), dried with sodium sulfate, evaporated and chromatographed on 1 Kg of silica gel eluting with 19:1 to 9:1 methylene chloride-ethanol to give 2-(2-bromophenyl)pyrrolidine (68.5 g).
	With methanol; sodium tetrahydroborate; acetic acid; at -65℃; for 1.5h;Inert atmosphere;	Compound 10; 2-(2-Bromophenyl)pyrrolidine5-(2-Bromophenyl)-3,4-dihydro-2H-pyrrole (compound 8; 393 mmol, 88 g) was dissolved in methanol (1300 ml_), then the acetic acid (330 ml_) was added and the solution cooled to -65 0C under a nitrogen atmosphere. Sodium borohydride (589 mmol, 22.28 g) was added portionwise over 1 hour. The reaction was stirred at -65 0C for 30 minutes, then the cooling bath was removed and the reaction mixture temperature was allowed to rise to room temperature. The bulk of the methanol was removed under vacuum then 5N HCI (950 ml_) was added and the solution extracted with ether (2 x 500 ml_). The aqueous solution was then basified with sodium hydroxide pellets (310 g) with ice-bath cooling, maintaining the reaction temperature less than 30 0C. The basified aqueous was then extracted with ethyl acetate (3 x 800 ml_), the combined organics washed with brine (800 ml_), dried with sodium sulfate, evaporated and chromatographed on 1 Kg of silica gel eluting with 19:1 to 9:1 methylene chloride- ethanol to give 2-(2-bromophenyl)pyrrolidine (68.5 g).

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2793 - 2797.
[2]Patent: US2010/113493,2010,A1 .Location in patent: Page/Page column 8.
[3]Patent: WO2010/52198,2010,A1 .Location in patent: Page/Page column 19.

2
[ 109086-16-0 ]
[ 129540-24-5 ]
1-[2-(2-Bromo-phenyl)-pyrrolidin-1-yl]-2-hydroxy-2-(4-methylsulfanyl-phenyl)-ethanone [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2793 - 2797.

3
[ 6091-64-1 ]
[ 129540-24-5 ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2793 - 2797.

4
[ 129540-24-5 ]
10-Bromo-6-(4-methylsulfanyl-phenyl)-2,3,6,10b-tetrahydro-1H-pyrrolo[2,1-a]isoquinolin-5-one [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2793 - 2797.

5
[ 129540-24-5 ]
[ 129540-07-4 ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2793 - 2797.

6
[ 129540-24-5 ]
[ 129540-07-4 ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2793 - 2797.

7
[ 129540-24-5 ]
[ 129540-08-5 ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2793 - 2797.

8
[ 24424-99-5 ]
[ 129540-24-5 ]
[ 1224945-44-1 ]

Yield	Reaction Conditions	Operation in experiment
98.1%	With dmap; triethylamine; In dichloromethane; at 20℃; for 16h;	A mixture solution of 2- (2-bromophenyl) pyrrolidine (1.13 g, 5 mmol), Boc 2O (2.16 g, 10 mmol), TEA (1.01 g, 10 mmol) and DMAP (cat) in DCM (20 mL) was stirred at room temperature for 16hrs. Then the mixture solution was concentrated, and the residue was purified by chromatography on silica-gel (eluting with 100%PE to PE /EA = 5 /1) to give the product (1.6 g, 98.1%) as a colorless oil. MS (ESI, m/e) [M+1] + 270.0, 272.0
	In tetrahydrofuran;	Compound 18 tert-Butyl <strong>[129540-24-5]2-(2-bromophenyl)pyrrolidine</strong>-1-carboxylate To a solution of <strong>[129540-24-5]2-(2-bromophenyl)pyrrolidine</strong> (compound 10; 257 mmol, 58 g) in dry tetrahydrofuran (870 mL), cooled with a water bath, was added di-tert-butyl dicarbonate (264 mmol, 57.7 g) in tetrahydrofuran (150 mL) dropwise over 30 minutes. The cooling bath was removed and the reaction stirred at room temperature for two days. The solvent was removed in vacuo and the residue taken up in methylene chloride (1 L), washed with 0.5M Citric acid (400 mL), brine (500 mL) and dried over sodium sulfate. Crystallisation from iso-hexane gave tert-butyl <strong>[129540-24-5]2-(2-bromophenyl)pyrrolidine</strong>-1-carboxylate (42 g) and further tert-butyl <strong>[129540-24-5]2-(2-bromophenyl)pyrrolidine</strong>-1-carboxylate (33 g) was obtained by chromatography of the mother liquors on 800 g silica gel, eluting with heptane-ethyl acetate 9:1 to 3:1.
	In tetrahydrofuran; at 20℃;Cooling with water bath;	Compound 18; tert-Butyl <strong>[129540-24-5]2-(2-bromophenyl)pyrrolidine</strong>-1 -carboxylateTo a solution of <strong>[129540-24-5]2-(2-bromophenyl)pyrrolidine</strong> (compound W; 257 mmol, 58 g) in dry tetrahydrofuran (870 ml_), cooled with a water bath, was added di-tert-butyl dicarbo- nate (264 mmol, 57.7 g) in tetrahydrofuran (150 ml.) dropwise over -30 minutes. The cooling bath was removed and the reaction stirred at room temperature for two days. The solvent was removed in vacuo and the residue taken up in methylene chloride (1 L), washed with 0.5M Citric acid (400 ml_), brine (500 ml_) and dried over sodium sulfate. Crystallisation from iso-hexane gave tert-butyl <strong>[129540-24-5]2-(2-bromophenyl)pyrrolidine</strong>-1 -carboxylate (42 g) and further tert-butyl <strong>[129540-24-5]2-(2-bromophenyl)pyrrolidine</strong>-1 -carboxylate (33 g) was obtained by chromatography of the mother liquors on 80Og silica gel, eluting with heptane-ethyl acetate 9:1 to 3:1.

References: [1]Patent: WO2019/210828,2019,A1 .Location in patent: Paragraph 0182; 0183; 0184.
[2]Patent: US2010/113493,2010,A1 .Location in patent: Page/Page column 9.
[3]Patent: WO2010/52198,2010,A1 .Location in patent: Page/Page column 21.

9
C₁₃H₁₃N₃O₅ [ No CAS ]
[ 129540-24-5 ]
3-{2-[2-(2-bromophenyl)pyrrolidin-1-yl]-2-oxoethyl}-1-[(4-nitrophenyl)methyl]-1-(prop-2-yn-1-yl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1499 mg	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 18h;	General procedure: Ethyl ester derivatives (1 eq.) were dissolved in a 1 :1 mixture of THF/MeOH and treated with LiOH monohydrate (5 eq.) dissolved in water (Water/THF/MeOH ratio: 1 :2:2). The reaction was kept under stirring at RT for 2 hours, then the reaction mixture was concentrated, diluted with water and washed with DCM. The aqueous phase was treated with 1 N aqueous HCI until acidic pH and extracted several times with EtOAc. The combined ethyl acetate organic phases were dried over MgS04, filtered, and evaporated to afford the desired products, which were used directly in the next step. 2-(2-Bromophenyl)- pyrrolidine (1 eq.), carboxylic acid derivatives (1.1 eq.) and HATU (1.4 eq.) were dissolved in DMF. DIPEA (1.5 eq.) was added and the reaction mixture was stirred at room temperature for 18 hours. After this time, the reaction mixture was diluted with EtOAc and washed with water and brine. The organic layer was dried over MgS04, filtered and concentrated in vacuo. The crude product was purified by flash column chromatography eluting with MeOH in DCM. The desired compounds were obtained as an oily product.

References: [1]Chemical Science,2019,vol. 10,p. 542 - 547.
[2]Patent: WO2020/43831,2020,A1 .Location in patent: Page/Page column 15; 18; 36.

10
C₁₄H₁₆N₆O₅ [ No CAS ]
[ 129540-24-5 ]
3-{2-[2-(2-bromophenyl)pyrrolidin-1-yl]-2-oxoethyl}-1-[(1-methyl-1H-1,2,3-triazol-4-yl)methyl]-1-[(4-nitrophenyl)methyl]urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
311 mg	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 18h;	General procedure: Ethyl ester derivatives (1 eq.) were dissolved in a 1 :1 mixture of THF/MeOH and treated with LiOH monohydrate (5 eq.) dissolved in water (Water/THF/MeOH ratio: 1 :2:2). The reaction was kept under stirring at RT for 2 hours, then the reaction mixture was concentrated, diluted with water and washed with DCM. The aqueous phase was treated with 1 N aqueous HCI until acidic pH and extracted several times with EtOAc. The combined ethyl acetate organic phases were dried over MgS04, filtered, and evaporated to afford the desired products, which were used directly in the next step. 2-(2-Bromophenyl)- pyrrolidine (1 eq.), carboxylic acid derivatives (1.1 eq.) and HATU (1.4 eq.) were dissolved in DMF. DIPEA (1.5 eq.) was added and the reaction mixture was stirred at room temperature for 18 hours. After this time, the reaction mixture was diluted with EtOAc and washed with water and brine. The organic layer was dried over MgS04, filtered and concentrated in vacuo. The crude product was purified by flash column chromatography eluting with MeOH in DCM. The desired compounds were obtained as an oily product.

References: [1]Chemical Science,2019,vol. 10,p. 542 - 547.
[2]Patent: WO2020/43831,2020,A1 .Location in patent: Page/Page column 15; 18; 37.

11
C₁₃H₁₅N₇O₅ [ No CAS ]
[ 129540-24-5 ]
3-{2-[2-(2-bromophenyl)pyrrolidin-1-yl]-2-oxoethyl}-1-[(2-methyl-2H-1,2,3,4-tetrazol-5-yl)methyl]-1-[(4-nitrophenyl)methyl]urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
221 mg	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 18h;	General procedure: Ethyl ester derivatives (1 eq.) were dissolved in a 1 :1 mixture of THF/MeOH and treated with LiOH monohydrate (5 eq.) dissolved in water (Water/THF/MeOH ratio: 1 :2:2). The reaction was kept under stirring at RT for 2 hours, then the reaction mixture was concentrated, diluted with water and washed with DCM. The aqueous phase was treated with 1 N aqueous HCI until acidic pH and extracted several times with EtOAc. The combined ethyl acetate organic phases were dried over MgS04, filtered, and evaporated to afford the desired products, which were used directly in the next step. 2-(2-Bromophenyl)- pyrrolidine (1 eq.), carboxylic acid derivatives (1.1 eq.) and HATU (1.4 eq.) were dissolved in DMF. DIPEA (1.5 eq.) was added and the reaction mixture was stirred at room temperature for 18 hours. After this time, the reaction mixture was diluted with EtOAc and washed with water and brine. The organic layer was dried over MgS04, filtered and concentrated in vacuo. The crude product was purified by flash column chromatography eluting with MeOH in DCM. The desired compounds were obtained as an oily product.

References: [1]Chemical Science,2019,vol. 10,p. 542 - 547.
[2]Patent: WO2020/43831,2020,A1 .Location in patent: Page/Page column 15; 18; 38.

12
C₁₇H₂₀N₆O₇ [ No CAS ]
[ 129540-24-5 ]
C₂₇H₃₀BrN₇O₆ [ No CAS ]

References: [1]Chemical Science,2019,vol. 10,p. 542 - 547.

13
[ 129540-24-5 ]
[ 407-25-0 ]
1-(2-(2-bromophenyl)pyrrolidin-1-yl)-2,2,2-trifluoroethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
5 g	With triethylamine; In dichloromethane; at 0 - 20℃;Inert atmosphere;	Under inert N 2 atmosphere, to a solution of 2- (2-bromophenyl) pyrrolidine (4 g, 17.68 mmol) in DCM (100 mL) was added TEA (3.57 g, 35.36 mmol) at 0C and then trifluoroacetic anhydride (4.46 g, 21.22 mmol) dropwise. The mixture was stirred for overnight at room temperature. The reaction mixture was then poured into 100 mL of water, extracted with DCM (100 mL), washed with 50 mL of brine, dried over anhydrous Na 2SO 4. The solution was filtered and concentrated to give crude 1- (2- (2-bromophenyl) pyrrolidin-1-yl) -2, 2, 2-trifluoroethan-1-one (5.0 g) as a brown oil, which was used into next step without further purification.

References: [1]Patent: WO2019/210828,2019,A1 .Location in patent: Paragraph 0253; 0254; 0255.

14
[ 129540-24-5 ]
methyl 4'-(2-(2-cyclopropylphenyl)pyrrolidin-1-yl)-3-(5-((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[4,3-b]pyrrolo[3,2-e]pyridin-1(5H)-yl)-2',3',4',5'-tetrahydro[1,1'-biphenyl]-4-carboxylate [ No CAS ]