98545-64-3|Methyl 4-amino-2-bromobenzoate| Ambeed

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Quality Control of [ 98545-64-3 ] Purity: 95% SDS Specification

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Product Details of [ 98545-64-3 ]

CAS No. :	98545-64-3
Formula :	C₈H₈BrNO₂
M.W :	230.06
SMILES Code :	O=C(OC)C1=CC=C(N)C=C1Br
MDL No. :	MFCD00859376
Boiling Point :	No data available
InChI Key :	KZOQVTUWEHNNMH-UHFFFAOYSA-N
Pubchem ID :	5244418

Safety of [ 98545-64-3 ]

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

Computational Chemistry of [ 98545-64-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.12
Num. rotatable bonds	2
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	49.83
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	52.32 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.83
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	1.82
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.83
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.	2.06
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	1.65
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.84

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.65
Solubility	0.514 mg/ml ; 0.00223 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.	-2.54
Solubility	0.666 mg/ml ; 0.00289 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	-2.97
Solubility	0.244 mg/ml ; 0.00106 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	No
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	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.	-6.41 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	0.0
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)	1.55

Application In Synthesis of [ 98545-64-3 ]

* 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 [ 98545-64-3 ]

[ 98545-64-3 ] Synthesis Path-Downstream 1~35

1
[ 100959-22-6 ]
[ 98545-64-3 ]

Yield	Reaction Conditions	Operation in experiment
94.2%	With tin(II) chloride dihdyrate; In ethyl acetate; for 4h;Reflux;	To a solution of compound 20 (4.5g, 17.0mmol) in EtOAc (100mL) was added SnCl2·2H2O (38.3g, 0.17mol). The mixture was heated to reflux and stirred for 4h. The mixture was poured into saturated NaHCO3 (500mL) and EtOAc (370mL). The organic layer was washed with brine (300mL), and dried over anhydrous MgSO4. The residue after rotary evaporation was purified by column chromatography over silica gel to give compound 21 as a solid (3.68g, 94.2% yield). 1H NMR (400MHz, CDCl3): delta 7.75 (d, J=8.5 Hz, 1H), 6.92 (d, J=2.2Hz, 1H), 6.57 (dd, J=8.5, 2.2Hz, 1H), 4.04 (brs, 2H) and 3.86 (s, 3H) ppm; mp: 96-98C.
		To a suspension of 2-bromo-4-nitro-benzoic acid methyl ester [100959-22-6] (350 mg, 1.35 mmol) in MeOH (60 mL) were subsequently added tin powder (1.6 g, 13.5 mmol) and 3N aqueous HCI (27.8 mL, 83 mmol). The mixture was stirred overnight at RT. The liquid phase was decanted from the excess tin and neutralized by adding a saturated aqueous NaHC03 solution. An equal amount of water by volume was added and the water phase was extracted with EtOAc (3x). The combined organics were dried (Phase Separator) and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (eluent: EtOAc/c-hexane 1 :4) to give the title compound as yellow solid. MS (LC/MS): 230 [M+H]+; tR (HPLC conditions b): 2.89 min.

References: [1]Organic Letters,2013,vol. 15,p. 3234 - 3237.
[2]Chinese Chemical Letters,2011,vol. 22,p. 1411 - 1414.
[3]European Journal of Medicinal Chemistry,2014,vol. 81,p. 59 - 75.
[4]Organic Process Research and Development,2019,vol. 23,p. 1686 - 1694.
[5]Academia Republicii Populare Romine, Baza de Cercetari Stiintifice, Timisoara, Studii si Cercetari, Stiinte Chimice,1956,vol. 4,p. 175,178.
[6]Patent: WO2012/93101,2012,A1 .Location in patent: Page/Page column 236-237.

Yield	Reaction Conditions	Operation in experiment
36%	With sodium tetrahydroborate; nickel(II) acetate tetrahydrate; In water; acetonitrile; at 10 - 20℃;	General procedure: Variant C: Adapting a literature known protocol (Setamdideh, et al., Orient. J. Chem., 2011, 27(3), 991-996), to a solution of the aromatic nitro compound (10 mmol) in acetonitrile (MeCN) (20 mL) is added a solution of nickel(II) acetate tetrahydrate (Ni(OAc)2 4H20) (1.0 mmol) in water (2 mL). The reaction mixture is stirred vigorously at room temperature and subsequently cooled to about 10C (water/ice bath). Solid sodium borohydride (NaBH4) (40 mmol) is added in small portions upon which a black nickelboride precipitates (NiB2) (Note: The reaction is strongly exothermic and copious amounts of hydrogen gas are generated). The reaction mixture is stirred with warming to room temperature for 1-4 hours (TLC reaction control). Upon completion, the reaction mixture is diluted with ethyl acetate (EtOAc) (30 mL) and the organic solution is filtered over a short plug of Celite. The filtrate is washed with saturated aqueous sodium hydrogencarbonate (NaHC03) (1 x) and the aqueous layer is extracted with EtOAc (lx). The combined organic extracts are washed with brine, dried over anhydrous magnesium sulfate (MgS04), filtered, and the combined filtrates are evaporated under reduced pressure using a rotary evaporator. The crude material is purified as described under Variant A.; Following the General Procedure of Description 6 (Variant C), 4-ethyl-3-iodo- aniline (40b) was prepared from l-ethyl-2-iodo-4-nitro-benzene (40a) (9.0 g, 32.0 mmol), nickel(II) acetate tetrahydrate (Ni(OAc)2 4H20) (1.08 g, 4.3 mmol), and sodium borohydride (NaBH4) (7.0 g, 185 mmol) in a mixture of acetonitrile (MeCN)/water (110 mL, 10: 1, v/v). After extractive work-up and purification by silica gel column chromatography using an ethyl acetate (EtOAc)/hexane gradient as eluent (EtOAc/hexane = 1 :5? EtOAc/hexane = 1 :4, v/v), 5.2 g (65% yield) of the target compound (40b) were obtained as a yellow solid. M.p.: 35.2-38.0C. Rf. -0.30 (EtOAc/hexane = 1 :4, v/v). 1H MR (300 MHz, CDC13): delta 7.18 (d, J = 2.7 Hz, 1H), 6.98 (d, J= 8.4 Hz, 1H), 6.62 (dd, J= 8.1, 2.7 Hz, 1H), 2.62 (q, J= 7.5 Hz, 2H), 2.54 (br. s, 2H), 1.15 (t, J= 7.2 Hz, 3H) ppm. LC/MS: Rt = 2.040 min; -100% purity by AUC at lambda = 254 nm; ESI (pos.) mlz = 248.10 (M+H+)+.
		methyl 4-amino-2-bromobenzoate m.p. 93-95 C.

3
[ 100959-22-6 ]
[ 7439-89-6 ]
[ 98545-64-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With ammonium chloride; In aqueous 2-propanol;	Example 54C methyl-2-bromo-4-aminobenzoate A solution of methyl 2-bromo-4-nitrobenzoate (970 mg, 3.73 mmol), iron powder 1.25 g (22.4 mmol) and ammonium chloride (239 mg, 4.48 mmol) in aqueous 2-propanol (20%, 15 mL) was heated to reflux for 30 minutes, cooled, filtered, and concentrated under reduced pressure. The residue was partitioned between diethyl ether (20 mL) and water (5 mL). The organic layer was washed with brine (1*5 mL), dried (MgSO4), filtered, and concentrated to provide the titled compound (813 mg, 95%).

References: [1]Patent: US2002/35137,2002,A1 .

4
[ 181132-65-0 ]
[ 98545-64-3 ]
[ 200879-15-8 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; triethylamine; In dichloromethane;	Step b) Methyl 2-Bromo-4-[(2-pyridin-2-yl-benzoyl)amino]benzoate A solution of <strong>[98545-64-3]methyl 2-bromo-4-amino benzoate</strong> (3 g, 13 mmol) and triethylamine (2.5 ml, 18 mmol) in dichloromethane (50 ml) was cooled to 0 and was treated with a slurry of 2-(pyridin-2-yl)benzoyl chloride in dichloromethane (20 ml). Stirring at room temperature was maintained for 4 hours. The reaction was quenched with 20% acetic acid, wash sequentially with saturated aqueous sodium bicarbonate, water then saturated brine solution. The solution was dried (MgSO4), filtered and concentrated in vacuo to give 5.23 g of a white foam. MS (+FAB) m/z 411/413 (M+H)+. Analysis for: C20H15BrN2O3 Calcd: C, 58.41; H, 3.68; N, 6.81. Found: C, 57.73; H, 3.66; N, 6.54.
5.23 g (97%)	With acetic acid; triethylamine; In dichloromethane;	Step b) Methyl 2-Bromo-4-[(2-pyridin-2-yl-benzoyl)amino]benzoate A slurry of 2-(pyridin-2-yl)benzoyl chloride in dichloromethane (20 ml) was added to a solution of <strong>[98545-64-3]methyl 2-bromo-4-amino benzoate</strong> (3 g, 13 mmol) and triethylamine (2.5 ml, 18 mmol) in dichloromethane (50 ml) which was cooled to 0 C. Stirring at room temperature was maintained for 4 hours. The reaction was quenched with 20% acetic acid, wash sequentially with saturated aqueous sodium bicarbonate, water then saturated brine solution. The solution was dried (MGSO4), filtered and concentrated in vacuo to give 5.23 g (97%) of a colorless foam. MS (+FAB) m/z: 411/413 (M+H)+.
5.23 g (97%)	With acetic acid; triethylamine; In dichloromethane;	Step b) Methyl 2-Bromo-4-[(2-pyridin-2-yl-benzoyl)amino]benzoate A slurry of 2-(pyridin-2-yl)benzoyl chloride in dichloromethane (20 ml) was added to a solution of <strong>[98545-64-3]methyl 2-bromo-4-amino benzoate</strong> (3 g, 13 mmol) and triethylamine (2.5 ml, 18 mmol) in dichloromethane (50 ml) which was cooled to 0 C. Stirring at room temperature was maintained for 4 hours. The reaction was quenched with 20% acetic acid, wash sequentially with saturated aqueous sodium bicarbonate, water then saturated brine solution. The solution was dried (MgSO4), filtered and concentrated in vacuo to give 5.23 g (97%) of a colorless foam. MS (+FAB) m/z: 411/413 (M+H)+. Analysis for: C20H15BrN2O3 Calcd: C, 58.41; H, 3.68; N, 6.81. Found: C, 57.73; H, 3.66; N, 6.54.

In dichloromethane; at 0 - 20℃; for 4h;

A solution of <strong>[98545-64-3]methyl 2-bromo-4-amino benzoate</strong> (3 g, 13 mmol) and triethylamine (2.5 ml, 18 mmol) in dichloromethane (50 ml) was cooled to 0 and was treated with a slurry of 2-(pyridin-2-yl)benzoyl chloride in dichloromethane (20 ml). Stirring at room temperature was maintained for 4 hours. The reaction was quenched with 20% acetic acid, wash sequentially with saturated aqueous sodium bicarbonate, water then saturated brine solution. The solution was dried (MgSO4), filtered and concentrated in vacuo to give 5.23 g of a white foam. MS (+FAB) m/z 411/413 (M+H)+. Analysis for: C20H15BrN2O3 Calcd: C, 58.41; H, 3.68; N, 6.81. Found: C, 57.73; H, 3.66; N, 6.54

References: [1]Patent: US5880122,1999,A .
[2]Patent: US5700796,1997,A .
[3]Patent: US5753648,1998,A .
[4]Patent: EP1021444,2003,B1 .Location in patent: Page/Page column 29.

5
[ 696-59-3 ]
[ 98545-64-3 ]
[ 1344109-43-8 ]

Yield	Reaction Conditions	Operation in experiment
84.3%	In ethyl acetate; for 4h;Reflux;	To a solution of compound 21 (3g, 13.0mmol) in AcOH (50mL) was added 2,5-dimethoxytetrahydrofuran (2.15g, 16.3mmol). The mixture was heated to reflux and stirred for 4h. After evaporation, the mixture was dissolved in EtOAc, washed with saturated NaHCO3, and dried over anhydrous Na2SO4. The residue after rotary evaporation was purified by column chromatography over silica gel to give compound 22 as a solid (3.06g, 84.3% yield).1H NMR (400MHz, CDCl3): delta 7.92 (d, J=8.5Hz, 1H), 7.70 (d, J=2.3Hz, 1H), 7.35 (dd, J=8.5, 2.3Hz, 1H), 7.10 (t, J=2.2Hz, 2H), 6.38 (t, J=2.2Hz, 2H) and 3.93 (s, 3H) ppm; mp: 50-53C.

References: [1]Chinese Chemical Letters,2011,vol. 22,p. 1411 - 1414.
[2]European Journal of Medicinal Chemistry,2014,vol. 81,p. 59 - 75.

6
[ 7745-93-9 ]
[ 98545-64-3 ]

References: [1]Chinese Chemical Letters,2011,vol. 22,p. 1411 - 1414.
[2]European Journal of Medicinal Chemistry,2014,vol. 81,p. 59 - 75.

7
[ 16426-64-5 ]
[ 98545-64-3 ]

References: [1]Chinese Chemical Letters,2011,vol. 22,p. 1411 - 1414.
[2]Organic Letters,2013,vol. 15,p. 3234 - 3237.
[3]European Journal of Medicinal Chemistry,2014,vol. 81,p. 59 - 75.
[4]Patent: US2014/256817,2014,A1 .

8
[ 98545-64-3 ]
[ 1344109-47-2 ]

References: [1]Chinese Chemical Letters,2011,vol. 22,p. 1411 - 1414.
[2]European Journal of Medicinal Chemistry,2014,vol. 81,p. 59 - 75.

9
[ 98545-64-3 ]
[ 1344109-52-9 ]

References: [1]Chinese Chemical Letters,2011,vol. 22,p. 1411 - 1414.
[2]European Journal of Medicinal Chemistry,2014,vol. 81,p. 59 - 75.

10
[ 98545-64-3 ]
[ 1344109-66-5 ]
[ 1344109-55-2 ]

References: [1]Chinese Chemical Letters,2011,vol. 22,p. 1411 - 1414.
[2]European Journal of Medicinal Chemistry,2014,vol. 81,p. 59 - 75.

11
[ 98545-64-3 ]
[ 1344109-58-5 ]
[ 1344109-67-6 ]

References: [1]Chinese Chemical Letters,2011,vol. 22,p. 1411 - 1414.
[2]European Journal of Medicinal Chemistry,2014,vol. 81,p. 59 - 75.

12
[ 98545-64-3 ]
[ 1344109-70-1 ]
[ 1344109-59-6 ]

References: [1]Chinese Chemical Letters,2011,vol. 22,p. 1411 - 1414.
[2]European Journal of Medicinal Chemistry,2014,vol. 81,p. 59 - 75.

13
[ 98545-64-3 ]
[ 1344109-62-1 ]

References: [1]Chinese Chemical Letters,2011,vol. 22,p. 1411 - 1414.
[2]European Journal of Medicinal Chemistry,2014,vol. 81,p. 59 - 75.

14
[ 98545-64-3 ]
[ 1344109-64-3 ]

References: [1]Chinese Chemical Letters,2011,vol. 22,p. 1411 - 1414.
[2]European Journal of Medicinal Chemistry,2014,vol. 81,p. 59 - 75.

15
[ 856794-72-4 ]
[ 98545-64-3 ]

References: [1]Chinese Chemical Letters,2011,vol. 22,p. 1411 - 1414.
[2]European Journal of Medicinal Chemistry,2014,vol. 81,p. 59 - 75.

16
[ 98545-64-3 ]
[ 1440546-78-0 ]

References: [1]Organic Letters,2013,vol. 15,p. 3234 - 3237.
[2]Patent: US2014/256817,2014,A1 .

17
[ 98545-64-3 ]
[ 1440546-89-3 ]

References: [1]Organic Letters,2013,vol. 15,p. 3234 - 3237.

18
[ 98545-64-3 ]
[ 101085-03-4 ]

Yield	Reaction Conditions	Operation in experiment
41.1%	With sulfuric acid; sodium nitrite; In water; ethyl acetate;	Finally, a solution of sulfuric acid (98%, 6 mL) in H2O (75 mL) was added to <strong>[98545-64-3]methyl 4-amino-2-bromobenzoate</strong> (1.23 g, 5.38 mmol) and the resulting suspension was heated to 90 C., then stirred for 5 h at this temperature. The reaction mixture was cooled to 0 C. and a solution of NaNO2 (384 mg, 5.57 mmol) in H2O (5 mL) was added dropwise, then the reaction was allowed to warm to ambient temperature. The reaction mixture was then added to a solution of sulfuric acid (98%, 6 mL) in H2O (75 mL) that had been preheated to 90 C. The reaction mixture was stirred at 90 C. for 1 h, and then allowed to cool. The reaction mixture was partitioned between EtOAc (200 mL) and aqueous solution. The organic layer was collected, dried over anhydrous Na2SO4, filtered, concentrated and purified by silica column chromatography (35% EtOAc in hexanes) to afford compound 10 in 41.1% (508 mg) yield as a light brown solid. 1H-NMR (CDCl3, 400 MHz) delta 7.76 (1H, d, J=8.8 Hz, Ar), 7.09 (1H, s, Ar), 6.75 (1H, d, J=8.8 Hz, Ar), 3.84 (3H, s, OCH3); 13C-NMR (CDCl3, 100 MHz) delta 166.2, 160.3, 133.5, 123.4, 122.1, 121.4, 114.3, 52.1; MS (ESI) m/z Calcd for C8H7BrO3 (M+): 230.0, Found: 231.0 (M+H+).

References: [1]Organic Process Research and Development,2019,vol. 23,p. 1686 - 1694.
[2]Organic Letters,2013,vol. 15,p. 3234 - 3237.
[3]Patent: US2014/256817,2014,A1 .Location in patent: Page/Page column.

19
[ 98545-64-3 ]
[ 17100-65-1 ]

References: [1]Organic Letters,2013,vol. 15,p. 3234 - 3237.
[2]Patent: US2014/256817,2014,A1 .

20
[ 98545-64-3 ]
[ 1440546-79-1 ]

References: [1]Organic Letters,2013,vol. 15,p. 3234 - 3237.
[2]Patent: US2014/256817,2014,A1 .

21
[ 98545-64-3 ]
[ 1440546-80-4 ]

References: [1]Organic Letters,2013,vol. 15,p. 3234 - 3237.
[2]Patent: US2014/256817,2014,A1 .

22
[ 98545-64-3 ]
[ 1615684-94-0 ]