1571-08-0|Methyl 4-formylbenzoate| Ambeed

Structure of Methyl 4-formylbenzoate
CAS No.: 1571-08-0

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Quality Control of [ 1571-08-0 ] Purity: 98% SDS Specification

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Product Details of [ 1571-08-0 ]

CAS No. :	1571-08-0
Formula :	C₉H₈O₃
M.W :	164.16
SMILES Code :	C1=C(C(OC)=O)C=CC(=C1)C=O
MDL No. :	MFCD00006950
InChI Key :	FEIOASZZURHTHB-UHFFFAOYSA-N
Pubchem ID :	15294

Safety of [ 1571-08-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H312-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 1571-08-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.11
Num. rotatable bonds	3
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	43.11
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	43.37 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.71
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	1.49
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.29
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.	1.28
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	1.85
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.52

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.97
Solubility	1.77 mg/ml ; 0.0108 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.01
Solubility	1.61 mg/ml ; 0.00981 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	-2.41
Solubility	0.634 mg/ml ; 0.00386 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	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	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.	-6.24 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	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)	1.04

Application In Synthesis of [ 1571-08-0 ]

* 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.

Upstream synthesis route of [ 1571-08-0 ]
Downstream synthetic route of [ 1571-08-0 ]

[ 1571-08-0 ] Synthesis Path-Upstream 1~3

1
[ 67-56-1 ]
[ 120-61-6 ]
[ 23405-32-5 ]
[ 6908-41-4 ]
[ 75164-88-4 ]
[ 1571-08-0 ]

References: [1] Chemistry Letters, 1980, p. 483 - 486.

2
[ 2031-62-1 ]
[ 1571-08-0 ]
[ 146781-28-4 ]

Yield	Reaction Conditions	Operation in experiment
94%	Stage #1: With dicarbonyl(pentamethylcyclopentadienyl)(4-methoxyphenyl)iron In dichloromethane for 4 h; Inert atmosphere; Irradiation; Schlenk technique Stage #2: With sodium hydroxide In methanol; waterSchlenk technique; Inert atmosphere	General procedure: In a Schlenk tube under 1 atm of argon, a solution of the substrate (2 mmol, 1 equiv), the precatalyst (0.04 mmol, 0.02 equiv), and the silane (3 mmol, 1.5 equiv) in methylene chloride (15 mL) was irradiated for 4h. After removal of the solvent, methanol (5 mL) and aqueous NaOH solution (2.5 M, 5 mL) were added and the resulting suspension was stirred overnight. Neutralization with aqueous HCl solution (2 M, 30 mL) and brine (20 mL) followed by standard workup gave the desired products as pure yellow oils.

References: [1] Tetrahedron Letters, 2012, vol. 53, # 37, p. 5015 - 5018.

3
[ 1571-08-0 ]
[ 1403783-31-2 ]

References: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 9891 - 9899.

[ 1571-08-0 ] Synthesis Path-Downstream 1~42

1
[ 67-56-1 ]
[ 120-61-6 ]
[ 23405-32-5 ]
[ 6908-41-4 ]
[ 75164-88-4 ]
[ 1571-08-0 ]

References: [1]Chemistry Letters,1980,p. 483 - 486.

2
[ 109-97-7 ]
[ 1571-08-0 ]
[ 22112-83-0 ]

Yield	Reaction Conditions	Operation in experiment
39%	With acetic acid; for 4h;Reflux;	Meso-tetrakis[4-(methoxycarbonyl)phenyl]porphyrinwas made through modifying A. D. Adler-f. R. Longomethod [35]. First, 2.33mmol of freshly distilled pyrroleand 2.33mmol of p-methoxycarbonylbenzaldehyde wereadded in 200ml acetic acid in a typical reaction. Then, themixture was refluxed for 4h and cooled based on the roomtemperature. The mixture was added to 100ml methanolin an ice bath after cooling. The purple crystals were filtratedand washed through using methanol and hot distilledwater. In addition, column chromatography (Silica gel, ethylacetate/n-hexane = 20:1 as an eluent) was used for purifyingcrude product, which resulted in creating a desiredpurple solid of meso-tetrakis[4-(methoxycarbonyl)phenyl]porphyrin(H2TMCPP) (39%).
37%	With acetic acid; for 4h;Reflux;	Meso-tetrakis[4-(methoxycarbonyl)phenyl]porphyrin wasmade through modifying of A. D. Adler-F. R. Longo method[25]. Briefly, in a typical reaction, 2.33 mmol of freshly distilledpyrrole and 2.33 mmol of p-methoxycarbonylbenzaldehydewere added into 200 mL acetic acid. The mixturewas refluxed for 4 h and cooled based on the room temperature.After cooling, the mixture was added to 100 ml methanolin an ice bath. The purple crystals were filtrated andwashed with methanol and hot distilled water. Then, crudeproduct was purified by column chromatography (silica gel,ethyl acetate /n-hexane = 20:1 as an eluent), and a desiredpurple solid of meso-tetrakis[4-(methoxycarbonyl)phenyl]porphyrin was obtained (37%).
30%	With propionic acid; at 80 - 140℃; for 1h;	Methyl 4-formylbenzoate (2.5g, 15.24mmol) and propionic acid (70ml) were added toa 150ml three-necked flask and heated to 80. The freshly distilled pyrrole(1ml,14.41mmol, dissolved in 10ml propionic acid) was added into the flask dropwise andthen the mixture was heated to 140. After refluxing for 1h, the solution was cooled to room tempreture and mathanol(30ml) was added into the flask and put into thefreezer for overnight. The solids were filtered out and then applied to silica gelcolumn using CH2Cl2 as eluent. Meso-tetra(4-methoxycarbonylphenyl)porphyrin(TCMPP) was obtained and the yield was 30%.MS (ESI): m/z = 847.7 [M+H]+, calcd. for C52H38N4O8 : 846.8; 1H NMR ( 400 MHz,CDCl3, TMS) δ (ppm) = 8.92 (s, 8H, pyrrole ring), 8.17-8.25(d, 16H, -C6H4), 4.08(s,12H, -CH3), -2.90 (s, 2H, pyrrloe NH); IR (KBr) υ (cm-1) : 3320, 2947, 2894, 1720,1600, 1555, 1435, 963.

23%	With propionic acid; at 60℃; for 24.5h;	After completely dissolving methyl-4-formylbenzoate (0.086 mol, 14.41 g) in propionic acid (250 mL) at 60C using a 500 mL 2-neck flask,Pyrrole (0.086 mol, 6.09 mL) dissolved in propionic acid (20 mL) was added dropwise over 30 minutes.Thereafter, the mixture was reacted by refluxing for 24 hours. After the reaction, the mixture was cooled to room temperature,Refrigerated for 2 hours. Then, the precipitate was recovered using suction filtration, and the recovered precipitate was ethanol,Washed with ethyl acetate and tetrahydrofuran (THF), respectively. The collected and washed precipitate was dried in an oven (70 C.) for 12 hours, As a pure product (TCPPCOOMe), a purple powder (4.9 mmol, 4.2 g, yield 23%) was obtained.
23%	With propionic acid; at 140℃; for 2h;Reflux; Darkness;	Pyrrole (0.69 mL, 0.01 mol), methyl p-formylbenzoate (1.64 g, 0.01 mol) and propionic acid (50 mL) were added in a three necked flask (100 mL). The resolutingsolution was refluxed for 2 h at 140 C in darkness. Then, solid powders wereobtained upon drying under vacuum. The final product was purified by columnchromatography to obtain a purple solid (0.48 g, 23%). 1H NMR (400 MHz, CDCl3 ):δ 8.83 (s, 8H), 8.46 (d, J = 10.4 Hz, 8H), 8.30 (d, J = 9.5 Hz, 8H), 4.12 (s, 12H), -2.78(s, 2H) (Fig. S1). m/z = 846.7 (Fig. S2).
21%	With propionic acid; for 12h;Reflux; Darkness;	pyrrole (3.0mL, 0.043mol) and methyl 4-formylbenzoate (6.9g, 0.042mol) were added to propionic acid (∼120mL) in a 500-mL flask, and the solution was refluxed for 12h in darkness. After that, the reaction mixture was cooled to room temperature and solids were collected by suction filtration and the washed with ethanol and methanol to give purple crystals (2g, 2.36mmol, 21 % yield).
20%	With propionic acid; at 150℃; for 12h;Darkness;	Methyl 4-formyl benzoate (2.5 g, 15.24mmol) in 25 mL of propionicacid, added pyrrole (1.02 g, 15.24 mmol) slowly in drops and it washeated (150 C) for 12 h (dark) and cooled followed by filtration to obtainedpurple solid which was purified by column chromatography.Yield (650 mg, 20%).1H NMR (CDCl3, 600 MHz), δ (ppm): -2.88 (s, 2H), 4.03 (s, 12H),8.20 (d, 8H), 8.36 (d, 8H), 8.73 (s, 8H) (Fig. S1). ESI-MS: m/z calcd.846.3, found 847.3 [M + H+] (Fig. S2).
	With propionic acid;Reflux;	General procedure: Porphyrin ligands were synthesized by the method of Alder with some modifications [25]. In a 100 mL of flask with three necks,0.015 mol of corresponding benzaldehyde was dissolved in 30 mL of propionic acid solution. The mixture was heated at reflux temperature with vigorous stirring. Subsequently, 0.015 mol of freshly distilled pyrrole solved in propionic acid solution (5 mL) was slowly added intothe above mixture. After a period of time of reaction, the mixture solution was cooled to room temperature and placed in the refrigerator overnight. Then the purple solid was filtered and washed with hot water and ethanol and dried at 80 C for 8 h. The crude product was purified via column chromatography using neutral alumina (100-200 mesh size) with chloroform or dichloromethane as eluent.
	In acetic anhydride; propionic acid;	General procedure: meso-5,10,15,20-tetraphenylporphyrins were prepared by following reported procedures24-28 via condensation reactions of the corresponding benzaldehyde with pyrrole in a mixed solvent of propionic acid and acetic anhydride. The amino functional group was obtained by reduction of nitro group using SnCl2/HCl. Carboxyl group was prepared by base-catalysed hydrolysis of ester functionality. A subsequent cobaltmetalation using Co(OAc)2•4H2O as the metal salt in DMF under reflux conditions afforded the desired cobalt complexes.
		In a reaction vessel,Pyrrole (1.48 g),Methyl terephthalaldehyde (3.60 g),Chloroform (600 mL) and ethanol (9 mL) were added.There,Boron trifluoride (0.94 g) was added dropwise,The mixture was stirred for 2 hours.To this solution,2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (3.74 g) was added,And the mixture was further stirred for 1 hour.The reaction solution was passed through Celite and silica gel,The filtrate was concentrated to obtain a crude product.This was developed and separated with a silica gel column,The product (5,10,15,20-tetrakis(4-methoxycarbonylphenyl)-21H, 23H-porphyrin, 0.45 g) was obtained.
	With propionic acid; at 128℃; for 1.5h;	a.5,10,15,20-tetrakis(4-carboxymethyl ester)phenylporphyrinSynthesis:First, freshly steamed pyrrole and propionic acid by distillation under reduced pressure. In a 500 ml three-necked flask, 7.5 g (45 mmol) of methyl p-formylbenzoate and 200 mL of propionic acid were added.Magnetically stir and heat to 128 C, dissolve 3.1 mL (45 mmol) of pyrrole in 10 mLPropionic acid, slowly added to the propionic acid solution by drop using a constant pressure dropping funnel (about 10 min),The reaction was about 1.5 h. Stop heating, when the reaction system is cooled to below 80 C,With sufficient agitation, add 200 mL of absolute ethanol.Put it in the refrigerator and cool it overnight, and filter it to obtain a purple-black crude product.The crude product was washed several times with secondary water and absolute ethanol, respectively.Drying at 40 C under vacuum, and then separating the crude product on a silica gel column.After the first green ribbon is removed with dichloromethane as the eluent,Then use dichloromethane: ethyl acetate 2:20 as the eluent,The purple first ribbon was collected and dried to give a bright purple product.
	With propionic acid; at 145℃; for 2h;Inert atmosphere; Darkness;	General procedure: Tetraphenylporphyrin (TPP), tetrakis(2-chlorophenyl)porphyrin (T(2-Cl)PP), tetrakis(3-chlorophenyl)porphyrin (T(3-Cl)PP), tetrakis(4-chlorophenyl)porphyrin (T(4-Cl)PP), tetrakis(4-fluorophenyl)porphyrin (T(4-F)PP), tetrakis(4-methylphenyl)porphyrin (T(4 CH3)PP), tetrakis(4-methoxyphenyl)porphyrin (T(4 OCH3)PP), tetrakis(naphthalen-2-yl)porphyrin (T(2-Na.)P) and tetrakis(4-methoxycarbonylphenyl)porphyrin (T(4 COOCH3)PP) were synthesizedthrough condensation of the corresponding aromatic aldehydewith freshly distilled pyrrole in propionic acid according to the Adler-Longo method after some modifications (Eq. 1 in Scheme 1) [74-76].In the synthesis process, aromatic aldehyde (100 mmol) was dissolved inpropionic acid (300 mL) with stirring at the room temperature under theatmosphere of nitrogen. Then, the resultant solution was heated torefluxing (145 C), and freshly distilled pyrrole (100 mmol) was addeddropwise. After stirring and refluxing for 2.0 h under the protection oftin foil from ambient light, the resultant reaction mixture was cooled toroom temperature and kept standing at room temperature for 24.0 h.The collected precipitate from suction filtration was suspended inmethanol (200 mL) with stirring at room temperature for 6.0 h andwashed with methanol (2 × 100 mL) successively. At last, silica columnchromatography was employed for further purification using themixture of cyclohexane and dichloromethane as eluent (Vcyclohexane :Vdichloromethane = 6 : 1). All the obtained porphyrins were dried at 75 C for12.0 h under reduced pressure and characterized through FT-IR, 1HNMR, 13C NMR and ESI-MS. Details could be seen in the ElectronicSupplementary Information.
	In propionic acid; at 150℃; for 12h;	Pyrrole (3.0g, 0.043mol) and methyl p-formylbenzoate (6.9g, 0.042mol) were put into a 250ml Pyrrole (3.0g, 0.043mol), methyl p-formylbenzoate (6.9g, 0.042mol) and propionic acid (100mL) were added into a three-neck flask (250mL). The reaction was conducted at 150C for 12h. After reaction, the reaction mixture was cooled to room temperature, yielding black solid. After filtration, the solid was washed with ethanol and dried in vacuum to obtain purple porphyrin ester precursor. The precursor (1.95g) was dissolved in a mixed solvent (120mL, tetrahydrofuran / methanol=1:1). 60ml 2M KOH aqueous solution was added into the mixed solvent. The mixture was heated at 80Cfor 12h. After cooling to room temperature, the mixture was acidified with 1M HCl solution until no solid was produced. Meso-tetra(4-carboxyphenyl) porphyrin was obtained through washing operation and drying treatment. Meso-tetra(4-carboxyphenyl) porphyrin (violet crystal, 32.3%).
	In propionic acid; at 130℃; for 2h;Inert atmosphere;	Under N2 atmosphere, dissolve methyl p-formylbenzoate (8.2g) in propionic acid (150mL), turn on the stirring, and add the solution The temperature was raised to 130C, and newly distilled pyrrole (3.4 mL) was added dropwise. After the addition was completed, stirring was continued for 2 hours. It can be observed that the solution gradually changed from colorless to purple-black during the reaction. Then, it was cooled to room temperature, filtered to obtain a black precipitate, washed with methanol (100 mL) three times, filtered, and dried. Purified 5,10,15,20-(4-methyl formate phenyl) porphyrin was obtained by chromatography column method.
	With propionic acid; for 12h;Reflux;	Methyl p-formylbenzoate (6 mmol) was added to propionicacid (26 mL) in a 100-mL three-necked flask that covered with aluminumfoil. Distillated pyrrole (6 mmol) was added dropwise, andthe mixture was refluxed for 12 h. The participate was separatedby filtration and washed with methanol, ethyl acetate and THF.After drying, a purple solid was obtained as the pure product. Inthis study the concentration of the S1 in ethanol was 0.0007 M. (Scheme 2.). IR (KBr) (mmax/cm1): 3422, 3316, 2945, 1723, 1276,1105 cm1, 1H NMR (CDCl3, 300 MHz): d = 8.82 (s, 8H), 8.45 (d,J = 8.4 Hz, 8H), 8.30 (d, J = 8.4 Hz, 8H), 4.12 (s, 12H), 2.80 (s,2H) ppm.

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[61]Journal of the Electrochemical Society,2018,vol. 165,p. H481 - H487.
[62]Patent: JP2015/86268,2015,A .Location in patent: Paragraph 0191-0193.
[63]Patent: CN108586469,2018,A .Location in patent: Paragraph 0025; 0027; 0028.
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3
[ 35661-51-9 ]
[ 1571-08-0 ]
[ 74105-62-7 ]

References: [1]Synthesis,1980,p. 244 - 245.

4
[ 1193-24-4 ]
[ 109-77-3 ]
[ 1571-08-0 ]
4-(7-amino-6-cyano-4-oxo-3,5-dihydro-4<i>H</i>-pyrano[2,3-<i>d</i>]pyrimidin-5-yl)-benzoic acid methyl ester [ No CAS ]

References: [1]Russian Chemical Bulletin,2004,vol. 53,p. 2342 - 2344.

5
[ 50488-44-3 ]
[ 1571-08-0 ]
[ 461665-75-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1865 - 1870.

6
[ 1571-08-0 ]
air [ No CAS ]
[ 22112-83-0 ]

References: [1]Tetrahedron,1997,vol. 53,p. 12339 - 12360.

7
[ 1571-08-0 ]
[ 22112-83-0 ]

References: [1]Journal of Organic Chemistry,1987,vol. 52,p. 827 - 836.
[2]Polyhedron,2017,vol. 128,p. 85 - 94.

8
[ 1075-35-0 ]
[ 144-55-8 ]
[ 1571-08-0 ]
[ 241498-13-5 ]

Yield	Reaction Conditions	Operation in experiment
1.98 g (63%)	With triethylsilane; trifluoroacetic acid; In dichloromethane; ethyl acetate;	EXAMPLE 88 4-[(1-benzhydryl-5-chloro-2-methyl-1H-indol-3-yl)methyl]benzoic acid Step 1 To an ice-cold (0 C.) solution of trifluoroacetic acid (1.7 ml, 15 mmol) and triethylsilane (4.8 ml, 30 mmol) in CH2Cl2 (20 mL) was added a solution of <strong>[1075-35-0]5-chloro-2-methylindole</strong> (1.66 g, 10 mmol) and methyl 4-formylbenzoate (1.8 g, 11 mmol) in CH2Cl2 (50 mL) over a period of 5 min. The resulting homogeneous solution was stirred at 0 C. for 1 h and rt for 2 h, at which time EtOAc (150 mL) and aqueous sodium bicarbonate (to pH=8) was added. The organic layer was washed with water and brine, dried over MgSO4 and concentrated. Flash chromatography (Hex/EtOAc, 4/1) gave 1.98 g (63%) of desired intermediate as a light-tan solid.

References: [1]Patent: US6500853,2002,B1 .

9
[ 120-35-4 ]
[ 1571-08-0 ]
4-[(2-Methoxy-5-phenylcarbamoyl-phenylamino)-methyl]-benzoic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 221 4-[(2-Methoxy-5-phenylcarbamoyl-phenylamino)-methyl]-benzoic acid methyl ester The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide or 4-carbomethoxybenzaldehyde as starting materials, which are commercially available from Aldrich; m.p. 170-172 C.

References: [1]Patent: US6268387,2001,B1 .

10
[ 75-16-1 ]
[ 1571-08-0 ]
[ 84851-56-9 ]

Yield	Reaction Conditions	Operation in experiment
		Step 1: A solution of methyl 4-formylbenzoate (8 g, 48.7 mmol, 1 eq) in THF (150 ml_) was cooled to -78C. Methyl magnesium bromide (3M in Et2O, 16.2 ml_, 48.7 mmol, 1 eq) was added dropwise to the solution over 15 min. The resulting mixture was stirred 16h, allowing it to warm to room temperature. Upon quenching the reaction with saturated NH4CI, the organic layer was removed, washed with saturated NH4CI, dried over anhydrous MgSO4, filtered and evaporated to afford a crude yellow oil which was subjected to silica gel chromatography (0% to 50% EtOAc in hexanes) to afford the desired product as a free-flowing pale yellow oil.

References: [1]Organic process research and development,2020.
[2]Patent: WO2009/5646,2009,A2 .Location in patent: Page/Page column 159-160.

11
[ 1571-08-0 ]
[ 792-74-5 ]
[ 1233-73-4 ]

References: [1]Chemical Communications,2011,vol. 47,p. 2161 - 2163.

12
[ 62327-21-3 ]
[ 1571-08-0 ]
[ 683246-09-5 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of tert-butyl P,P-dimethylphosphonoacetate (Fluka, 1.43 g, 6.4 mmol) in THF (40 mL) was added NaH (Alderich, 60percent, 536 mg, 13.4 mmol) portionwise at rt over 30 min. Methyl 4-formylbenzoate (Alderich, 1.0 g, 6.09 mmol) was then added and the reaction mixture was stirred at rt for 4 hrs. The reaction was quenched with water and extracted with EtOAc. The organic layer was separated, and dried over Na2SO4. The mixture was then concentrated to give the crude 4-((E)-2-tert-butoxycarbonyl-vinyl)-benzoic acid methyl ester (1.89 g, 118percent).

References: [1]Patent: US2011/86854,2011,A1 .Location in patent: Page/Page column 23.

13
[ 2031-62-1 ]
[ 1571-08-0 ]
[ 146781-28-4 ]

Yield	Reaction Conditions	Operation in experiment
94%		General procedure: In a Schlenk tube under 1 atm of argon, a solution of the substrate (2 mmol, 1 equiv), the precatalyst (0.04 mmol, 0.02 equiv), and the silane (3 mmol, 1.5 equiv) in methylene chloride (15 mL) was irradiated for 4h. After removal of the solvent, methanol (5 mL) and aqueous NaOH solution (2.5 M, 5 mL) were added and the resulting suspension was stirred overnight. Neutralization with aqueous HCl solution (2 M, 30 mL) and brine (20 mL) followed by standard workup gave the desired products as pure yellow oils.

References: [1]Tetrahedron Letters,2012,vol. 53,p. 5015 - 5018.

14
[ 109-97-7 ]
[ 28785-06-0 ]
[ 1571-08-0 ]
5(p-methoxycarbonylphenyl)-10,15,20-tri(4-propylphenyl)porphyrin [ No CAS ]

References: [1]Chemistry - A European Journal,2012,vol. 18,p. 11388 - 11398,11.

15
[ 38956-79-5 ]
[ 1571-08-0 ]
C₁₄H₁₄N₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 60℃; for 0.5h;	General procedure: A mixture of corresponding hydrazinylpyridazine 1 or 5 (1 mmol) and aldehyde 2 (1.1 mmol) in ethanol (5 mL) was heated at 60 oC for 0.5 h. The formation of hydrazone was checked by TLC and the reaction mixture was cooled to rt. Oxone (1.5 mmol) was added to the mixture at rt followed by tetramethyl ammonium bromide (0.2 mmol) and the resulting mixture was heated at 60 oC for another 5 h. The mixture was cooled to rt and extracted with dichloromethane (2 × 25 mL), dried over anhydrous sodium sulphate and concentrated to obtain a residue which was purified by column chromatography using hexane/ethyl acetate as eluent to furnish the desired triazolopyridazines 4 and 7.
	In ethanol; at 60℃; for 0.5h;	General procedure: A mixture of corresponding hydrazinylpyridazine 1 or 5 (1 mmol) and aldehyde 2 (1.1 mmol) in ethanol (5 mL) was heated at 60 C for 0.5 h. The formation of hydrazone was checked by TLC and the reaction mixture was cooled to rt. Oxone (1.5 mmol) was added to the mixture at rt followed by tetramethyl ammonium bromide (0.2 mmol) and the resulting mixture was heated at 60 C for another 5 h. The mixture was cooled to rt and extracted with dichloromethane (2 × 25 mL), dried over anhydrous sodium sulfate and concentrated to obtain a residue which was purified by column chromatography using hexane/ethyl acetate as eluent to furnish the desired triazolopyridazines 4 and 7 (See reference no; 7 for supporting information).

References: [1]Journal of the Korean Chemical Society,2013,vol. 57,p. 606 - 611.
[2]Journal of the Korean Chemical Society,2014,vol. 58,p. 377 - 380.

16
[ 38956-79-5 ]
[ 1571-08-0 ]
methyl 4-(6-methyl[1,2,4]triazolo[4,3-b]pyridazin-3-yl)benzoate [ No CAS ]

References: [1]Journal of the Korean Chemical Society,2013,vol. 57,p. 606 - 611.
[2]Journal of the Korean Chemical Society,2014,vol. 58,p. 377 - 380.

17
[ 778531-36-5 ]
[ 22259-53-6 ]
[ 1571-08-0 ]
[ 1560895-57-9 ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 2334 - 2356.

18
[ 1560895-01-3 ]
[ 22259-53-6 ]
[ 1571-08-0 ]
methyl 4-(1-((1H-indol-3-yl)methyl)-4-hydroxy-3-isonicotinoyl-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)benzoate [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 2334 - 2356.

19
[ 1571-08-0 ]
[ 347174-05-4 ]
ethyl 4-(cyclohexylamino)-3-(4-(methoxycarbonyl)-benzylamino)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: SI, Figure 4. General procedure of the reductive amination reactions: synthesis of AA9-AA24 compounds (Tables 1 and 2). The <strong>[347174-05-4]ethyl 3-amino-4-(cyclohexylamino)benzoate</strong> (AA1) and derivatives (1 equiv.)and benzaldehyde (1 equiv) were heated in DCE for 1h at 80 oC in the presence of molecular sieves (4 A), then the mixture was cooled down to room temperature before addition of the NaBH(OAc)3 (1.6 equiv.) in small portions over 3h. The reaction mixture was stirred at room temperature under a nitrogen atmosphere for 17h. The reaction mixture was quenched with aqueous saturated NaHCO3, and the product was extracted with EtOAc. The EtOAc extract was dried (MgSO4), and the solvent was evaporated. The residue was purified by flash-column chromatography on silica gel, using a mixture of solvent of DCM: MeOH (50:1), to provide the desired AA9-AA24 compounds (Tables 1-2).

References: [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 5315 - 5320.

20
[ 1571-08-0 ]
[ 479353-63-4 ]