[ CAS No. 15764-16-6 ] {[proInfo.proName]}

Name: 15764-16-6|2,4-Dimethylbenzaldehyde|95%
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Product Citations

Selective and Cell-Active PBRM1 Bromodomain Inhibitors Discovered through NMR Fragment Screening

Shifali Shishodia ; Raymundo Nuñez ; Brayden P. Strohmier , et al. J. Med. Chem.,2022,65(20):13714-13735. DOI: 10.1021/acs.jmedchem.2c00864 PubMed ID: 36227159

Abstract: PBRM1 is a subunit of the PBAF chromatin remodeling complex that uniquely contains six bromodomains. PBRM1 can operate as a tumor suppressor or tumor promoter. PBRM1 is a tumor promoter in prostate cancer, contributing to migratory and immunosuppressive phenotypes. Selective chemical probes targeting PBRM1 bromodomains are desired to elucidate the association between aberrant PBRM1 chromatin binding and cancer pathogenesis and the contributions of PBRM1 to immunotherapy. Previous PBRM1 inhibitors unselectively bind SMARCA2 and SMARCA4 bromodomains with nanomolar potency. We used our protein-detected NMR screening pipeline to screen 1968 fragments against the second PBRM1 bromodomain, identifying 17 hits with Kd values from 45 μM to >2 mM. Structure–activity relationship studies on the tightest-binding hit resulted in nanomolar inhibitors with selectivity for PBRM1 over SMARCA2 and SMARCA4. These chemical probes inhibit the association of full-length PBRM1 to acetylated histone peptides and selectively inhibit growth of a PBRM1-dependent prostate cancer cell line.

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Product Details of [ 15764-16-6 ]

CAS No. :	15764-16-6	MDL No. :	MFCD00003340
Formula :	C₉H₁₀O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GISVICWQYMUPJF-UHFFFAOYSA-N
M.W :	134.18	Pubchem ID :	61814
Synonyms :

Calculated chemistry of [ 15764-16-6 ] Expand+

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	41.76
TPSA :	17.07 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.26 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.87
Log Po/w (XLOGP3) :	2.62
Log Po/w (WLOGP) :	2.12
Log Po/w (MLOGP) :	2.1
Log Po/w (SILICOS-IT) :	2.92
Consensus Log Po/w :	2.32

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.7
Solubility :	0.267 mg/ml ; 0.00199 mol/l
Class :	Soluble
Log S (Ali) :	-2.63
Solubility :	0.316 mg/ml ; 0.00235 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.09
Solubility :	0.11 mg/ml ; 0.000818 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.0

Safety of [ 15764-16-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 15764-16-6 ]

* 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 [ 15764-16-6 ]
Downstream synthetic route of [ 15764-16-6 ]

[ 15764-16-6 ] Synthesis Path-Upstream 1~3

1
[ 15764-16-6 ]
[ 16308-92-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: With sodium tetrahydroborate In methanol at 0℃; for 1 h;	Reference Example 58 (2,4-dimethylphenyl)methanol To a solution (100 mL) of 2,4-dimethylbenzaldehyde (10.4 g) in methanol was added sodium borohydride (0.83 g) at 0°C. The reaction mixture was stirred at 0°C for 1 hr, and the reaction mixture was concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound as a colorless oil (yield 10.8 g, yield quantitative). ¹H-NMR (CDCl₃) δ: 1.55 (1H, t, J = 5.4 Hz), 2.31 (3H, s), 2.33 (3H, s), 4.64 (2H, d, J = 5.4 Hz), 6.98-7.00 (2H, m), 7.19-7.22 (1H, m).

Reference： [1] Patent: EP1787991, 2007, A1, . Location in patent: Page/Page column 45
[2] Journal of the Chemical Society, 1907, vol. 91, p. 759
[3] Advanced Synthesis and Catalysis, 2007, vol. 349, # 10, p. 1633 - 1636
[4] Patent: EP1510512, 2005, A1, . Location in patent: Page/Page column 5-6
[5] Chemistry Letters, 2010, vol. 39, # 5, p. 500 - 501

2
[ 15764-16-6 ]
[ 16308-92-2 ]
[ 611-01-8 ]

Reference： [1] Gazzetta Chimica Italiana, 1902, vol. 32 II, p. 467
[2] Journal of the American Chemical Society, 1901, vol. 23, p. 600

3
[ 15764-16-6 ]
[ 1685-81-0 ]

Reference： [1] Monatshefte fur Chemie, 1996, vol. 127, # 2, p. 185 - 200
[2] Journal of Heterocyclic Chemistry, 1987, vol. 24, # 3, p. 677 - 682
[3] Bulletin de la Societe Chimique de France, 1965, p. 785 - 787
[4] Patent: US2011/53974, 2011, A1,

[ 15764-16-6 ] Synthesis Path-Downstream 1~98

1
[ 15764-16-6 ]
[ 528-44-9 ]

Yield	Reaction Conditions	Operation in experiment
91%		Comparative Example 5 Liquid-phase air oxidation was conducted in the same manner as in Comparative Example 3 except that the 50 mass% aqueous solution of FeBr3 was not used. As a result, trimellitic acid was obtained in 91% yield, a trimellitic acid bromide was obtained in 0.8% yield, dicarboxymethylbenzenes were obtained in 0.4% yield, trimellides were obtained in 2.1% yield, phthalic acid was obtained in 0.1% yield, and pyromellitic acid was obtained in 0.1% yield. In addition, a bromide ion residual ratio was 56%. Table 2 shows the results.

Reference： [1]Patent: EP1167335,2002,A2 .Location in patent: Page 4
[2]Patent: EP1167335,2002,A2 .Location in patent: Page 5
[3]Patent: EP1167335,2002,A2 .Location in patent: Page 5
[4]Patent: EP2269973,2011,A1 .Location in patent: Page/Page column 7
[5]Patent: EP1167335,2002,A2 .Location in patent: Page 5
[6]Patent: EP1167335,2002,A2 .Location in patent: Page 5

2
[ 16308-92-2 ]
[ 15764-16-6 ]

Yield	Reaction Conditions	Operation in experiment
	With tert.-butylhydroperoxide; In acetonitrile; at 60℃; for 2.5h;	(a) Oxidation of two alcohols, 4-methyl benzyl alcohol and <strong>[16308-92-2]2,4-dimethyl benzyl alcohol</strong> were studied using the copper(II) metallatriangles as catalyst, heterogeneously in acetonitrile at 60C. The time duration was 2.5h and ratio of catalyst: substrate: oxidant was fixed as 1:60:60 for each reaction. The progress of reaction was monitored by TLC. The catalyst was filtered, dried and washed with acetonitrile after each reaction and reutilized for the next reaction. The products formed were analyzed by GCMS. (b) The kinetics of the conversion of 4-methylbenzyl alcohol to 4-methylbenzaldehyde was studied spectrophotometrically. 0.16mmol of 4-methylbenzyl alcohol was mixed with 0.0042mmol of the copper(II) metallatriangle (1) in 10ml acetonitrile in the presence of 0.16 mmoles of tert.butyl hydroperoxide (TBHP) at 60C with rapid stirring. After every 5min, 20muL solution from the reaction mixture was taken in a quartz cuvette containing 2.0mL acetonitrile ant the solution scanned in the UV-range for the development of any new band. It is found that a new band immediately starts to arise at ?255nm. This band grows in intensity for nearly two hours and also splits into two bands viz at ?246 and 255nm suggesting the formation of 4-methylbenzoic acid after >1h of reaction. This procedure was repeated with different amount of catalyst (0.0014 and 0.0028 mmol) keeping the amount of 4-methylbenzyl alcohol same (i.e. 0.16 mmol). The rate of formation of 4-methylbenzaldehyde was determined by initial rate method this was obtained from the plot of concentration of aldehyde formed versus time.
>99%Chromat.	With oxygen; potassium carbonate; In toluene; at 90℃;Catalytic behavior;	General procedure: In a 5 ml glass flask, catalyst (10 mg, containing 0.2 mol% Pd), alcohol(0.5 mmol), K2CO3 (104 mg, 0.75 mmol) and H2O or toluene(2 mL) were added and reaction mixture was stirred continuously at90 C for the desired time under O2 atmosphere (from a balloon). Then,in the case of water as solvent, products were extracted with ethylacetate and the catalyst was recovered by an external magnet. Yields ofdesired products were determined by gas chromatography.

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 7507 - 7510
[2]Advanced Synthesis and Catalysis,2019,vol. 361,p. 2262 - 2267
[3]Synlett,2005,p. 607 - 610
[4]Monatshefte fur Chemie,1996,vol. 127,p. 185 - 200
[5]Chemische Berichte,1888,vol. 21,p. 3085
[6]Zeitschrift fur Naturforschung, B: Chemical Sciences,2006,vol. 61,p. 326 - 330
[7]Zeitschrift fur Naturforschung, B: Chemical Sciences,2006,vol. 61,p. 326 - 330
[8]Inorganica Chimica Acta,2013,vol. 399,p. 36 - 44
[9]Applied Catalysis A: General,2018,vol. 563,p. 185 - 195
[10]European Journal of Organic Chemistry,2019,vol. 2019,p. 3190 - 3194

3
[ 15764-16-6 ]
[ 16308-92-2 ]

Yield	Reaction Conditions	Operation in experiment
100%		Reference Example 58 (2,4-dimethylphenyl)methanol To a solution (100 mL) of 2,4-dimethylbenzaldehyde (10.4 g) in methanol was added sodium borohydride (0.83 g) at 0C. The reaction mixture was stirred at 0C for 1 hr, and the reaction mixture was concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound as a colorless oil (yield 10.8 g, yield quantitative). 1H-NMR (CDCl3) delta: 1.55 (1H, t, J = 5.4 Hz), 2.31 (3H, s), 2.33 (3H, s), 4.64 (2H, d, J = 5.4 Hz), 6.98-7.00 (2H, m), 7.19-7.22 (1H, m).
	With hydrogen;Ru/C; In tetrahydrofuran; at 100℃; under 30003.0 Torr; for 5h;Product distribution / selectivity;	COMPARATIVE EXAMPLE 2Direct hydrogenation of aromatic aldehyde using Ru-carbon catalyst; Into a 100-mL shaking autoclave, were charged 4.0 g of 2,4-dimethylbenzaldehyde, 0.8 g of a Ru-carbon powdery catalyst having a water content of 50% (5% by weight of 2,4-dimethylbenzaldehyde in terms of Ru) and 32 g of tetrahydrofuran, and the inner atmosphere was replaced with nitrogen gas twice and then with hydrogen gas three times. After adjusting the hydrogen pressure to 4.0 MPa, the temperature was raised to proceed the hydrogenation at 100C for 300 min. The reaction product solution taken out of the autoclave was filtered by a vacuum filter having a 1.0 mum PTFE membrane filter to remove the catalyst, thereby obtaining a colorless transparent filtrate. The filtrate was distilled by a rotary evaporator to remove tetrahydrofuran, and the residue was analyzed by gas chromatography. The conversion of 2,4-dimethylbenzaldehyde was 99%, and 2,4-dimethylbenzyl alcohol was obtained in a selectivity of 95%. No 2,4-dimethylcyclohexylaldehyde as the aimed product was obtained.

Reference： [1]Patent: EP1787991,2007,A1 .Location in patent: Page/Page column 45
[2]Journal of the Chemical Society,1907,vol. 91,p. 759
[3]Advanced Synthesis and Catalysis,2007,vol. 349,p. 1633 - 1636
[4]Patent: EP1510512,2005,A1 .Location in patent: Page/Page column 5-6
[5]Chemistry Letters,2010,vol. 39,p. 500 - 501

4
[ 15764-16-6 ]
[ 16308-92-2 ]
[ 611-01-8 ]

Reference： [1]Gazzetta Chimica Italiana,1902,vol. 32 II,p. 467

5
[ 3511-34-0 ]
[ 15764-16-6 ]
[ 71381-16-3 ]

Yield	Reaction Conditions	Operation in experiment
59%	With toluene-4-sulfonic acid In benzene for 0.5h; Heating;

Reference： [1]Galdino, Suely Lins; Da Rocha Pitta, Ivan; Luu-Duc, Cuong; Lucena, Beatriz; Olivera Correa Lima, Rosalia Maria [European Journal of Medicinal Chemistry, 1985, vol. 20, # 5, p. 439 - 442]

6
[ 141-82-2 ]
[ 15764-16-6 ]
[ 117391-54-5 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium acetate In ethanol for 6h; Heating;

Reference： [1]Rault, Sylvain; Dallemagne, Patrick; Robba, Max [Bulletin de la Societe Chimique de France, 1987, # 6, p. 1079 - 1083]

7
[ 70591-20-7 ]
[ 15764-16-6 ]
(Z)-2-(Benzhydrylidene-amino)-3-(2,4-dimethyl-phenyl)-acrylonitrile [ No CAS ]

Reference： [1]Journal of Chemical Research, Miniprint,1995,p. 1601 - 1638

8
[ 15764-16-6 ]
[ 134-81-6 ]
[ 111318-28-6 ]

Yield	Reaction Conditions	Operation in experiment
79%	With vanadatesulfuric acid; ammonium acetate; at 80℃; for 1h;	General procedure: In a round-bottom flask, the aldehyde (1 mmol), benzil or benzoin (1 mmol), ammonium acetate (2 mmol for 2,4,5-trisubstituted imidazoles and 1 mmol for 1,2,4,5-tetrasubstituted imidazoles) or aniline (1 mmol for 1,2,4,5-tetrasubstituted imidazoles) and VSA (10 mol %) were mixed thoroughly. The flask was heated at 80C under continuous stirring. After the its completion, the reaction as monitored by TLC (eluent/EtOAc/hexane = 1 : 4 vol.), acetone (10 mL) was added and the solid catalyst was then filtered and separated. The solvent was evaporated and the crude products were purified by column chromatography or recrystallization from ethanol (Tables 2 and 3). Then, the products were characterized by IR, 1H NMR, 13CNMR and also the comparison of their melting points with those reported in literature.

Reference： [1]Chemical Papers,2015,vol. 69,p. 1491 - 1499
[2]Bollettino Chimico Farmaceutico,1999,vol. 138,p. 24 - 29
[3]Letters in Organic Chemistry,2012,vol. 9,p. 351 - 355

9
[ 68039-49-6 ]
[ 15764-16-6 ]

Yield	Reaction Conditions	Operation in experiment
	at 280℃; substance of bp : 94 degree-96 degree;

Reference： [1]Holmes et al. [Canadian Journal of Research, Section B: Chemical Sciences, 1948, vol. 26, p. 248,252]

10
[ 15764-16-6 ]
[ 84-11-7 ]
2-(2,4-dimethylphenyl)-1H-phenanthro[9,10-d]imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With vanadatesulfuric acid; ammonium acetate; at 80℃; for 0.583333h;	General procedure: In a round-bottom flask, the aldehyde (1 mmol), benzil or benzoin (1 mmol), ammonium acetate (2 mmol for 2,4,5-trisubstituted imidazoles and 1 mmol for 1,2,4,5-tetrasubstituted imidazoles) or aniline (1 mmol for 1,2,4,5-tetrasubstituted imidazoles) and VSA (10 mol %) were mixed thoroughly. The flask was heated at 80C under continuous stirring. After the its completion, the reaction as monitored by TLC (eluent/EtOAc/hexane = 1 : 4 vol.), acetone (10 mL) was added and the solid catalyst was then filtered and separated. The solvent was evaporated and the crude products were purified by column chromatography or recrystallization from ethanol (Tables 2 and 3). Then, the products were characterized by IR, 1H NMR, 13CNMR and also the comparison of their melting points with those reported in literature.

Reference： [1]Heterocyclic Communications,2011,vol. 17,p. 79 - 81
[2]Chemical Papers,2015,vol. 69,p. 1491 - 1499
[3]Bollettino Chimico Farmaceutico,1999,vol. 138,p. 453 - 456

11
[ 15764-16-6 ]
benzaldehyde (1-methyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yl)-hydrazone [ No CAS ]
2-benzyl-3-(2,4-dimethylphenyl)-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57.21%	With piperidine; acetic acid; In N,N-dimethyl-formamide; isopropyl alcohol; at 120℃;	To a mixture containing 0.51 g (3.78 mmol) of 6-(N"- benzylidene-hydrazino)-3-me thyl-1H-pyrimidine-2,4-dione in 30 ml of N,N-dimethylformamide and 16 ml of isopropanol was added 0.77 g (3.15 mnol) of <strong>[15764-16-6]2,4-dimethyl benzaldehyde</strong> followed by 0.31 ml (3.15 mmol) of piperidine and 0.036 ml (0.63 mmol) of acetic acid. The reaction was heated to 120C under a nitrogen atmosphere overnight. The reaction was diluted with ethyl acetate and washed with water. The organic phase was dried over magnesium sulfate. Filtration, removal of solvent and purification of the residue via biotage eluting with 50% ethyl acetate/hexanes gave 0.68 g (57.21%) of product as a white solid. ¹H NMR (CDC13) No.: 2. 02 (s, 3H) , 2.39 (s, 3H) , 3. 31 (s, 3H) , 5.15 (ABq, J = 18.8 Hz, 2H), 7.03 - 7 .14 (m, 5H), 7.23 - 7 . 27 (m, 3H) , 9. 83 (s, 1H). MS Calcd. : 360; Found: 361 (M+H).

Reference： [1]Patent: WO2005/99688,2005,A2 .Location in patent: Page/Page column 150-151

12
[ 15764-16-6 ]
[ 1811-85-4 ]

Reference： [1]Molecules,2004,vol. 9,p. 449 - 458
[2]Monatshefte fur Chemie,1996,vol. 127,p. 185 - 200
[3]Journal of Heterocyclic Chemistry,1987,vol. 24,p. 677 - 682
[4]Gazzetta Chimica Italiana,1904,vol. 34 II,p. 121
[5]Justus Liebigs Annalen der Chemie,1906,vol. 347,p. 353
[6]Bulletin de la Societe Chimique de France,1965,p. 785 - 787
[7]Patent: US2011/53974,2011,A1

13
[ 15764-16-6 ]
[ 1685-81-0 ]

Reference： [1]Monatshefte fur Chemie,1996,vol. 127,p. 185 - 200
[2]Journal of Heterocyclic Chemistry,1987,vol. 24,p. 677 - 682
[3]Bulletin de la Societe Chimique de France,1965,p. 785 - 787
[4]Patent: US2011/53974,2011,A1

14
[ 15764-16-6 ]
[ 1439-36-7 ]
[ 70233-10-2 ]

Yield	Reaction Conditions	Operation in experiment
94%	In dichloromethane; at 60℃; for 20h;	1-Triphenylphosphoranilidene-2-propanone (49.08 g, 0.225mol) was added to a solution of <strong>[15764-16-6]2,4-dimethylbenzaldehyde</strong> (15.08 g, 0.112 mol) in dichloromethane (100 mL), and the mixture was heated at 60C for 20 hours. The reaction mixture was evaporated as it was. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane= 1:5) to give the title compound (18.32 g, 94%). 1H NMR (400MHz, CDCl3) delta 2.33 (s, 3H), 2.37 (s, 3H), 2.42 (s, 3H), 6.62 (d, J = 16.1 Hz, 1H), 7.00-7.08 (m, 2H), 7.48 (d,J = 8.4 Hz, 1H), 7.79 (d, J = 16.1 Hz, 1H).

Reference： [1]Patent: EP1364952,2003,A1 .Location in patent: Page/Page column 35
[2]Frontiers in Neural Circuits,2016,vol. 10

15
[ 51114-94-4 ]
[ 15764-16-6 ]
[ 20883-81-2 ]

Yield	Reaction Conditions	Operation in experiment
54%	With potassium tert-butylate; In tetrahydrofuran; at 0℃; for 3.16667h;	(Reference example 6) 4-(2,4-Dimethylphenyl)butyric acid (2-Carboxyethyl)triphenylphosphonium bromide (150 g, 361 mmol) was suspended in tetrahydrofuran (500 mL) and 2,4-dimethylbenzaldehyde (55.4 mL, 397 mmol) was added thereto. A solution of potassium t-butoxide (81.1 g, 722 mmol) in tetrahydrofuran (300 mL) was added thereto under nitrogen atmosphere over 10 minutes and the mixture was stirred under ice-cooling for 3 hours. Water was added to the reaction mixture to stop the reaction and the temperature of the liquid was returned to room temperature. The mixture was concentrated under reduced pressure, a 8N aqueous sodium hydroxide solution was added thereto to bring pH to 11 and ether was added thereto to separate it. A 12N aqueous hydrochloric acid solution was added to an aqueous phase to bring pH to 2 and ethyl acetate was added thereto to separate it. The thus obtained organic phase was separated, washed with water and a saturated aqueous NaCl solution and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (hexane:ethyl acetate, 10:1-6:1) to obtain 4-(2,4-dimethylphenyl)-3-butenoic acid (37.0 g, yield: 54percent). 10percent Palladium-carbon (7.96 g, 50percent hydrous) was added to a solution of the obtained 4-(2,4-dimethylphenyl)-3-butenoic acid (37.0 g, 195 mmol) in methanol (400 mL) and the mixture was stirred at room temperature under a hydrogen atmosphere for 3 hours. After the palladium-carbon in the reaction mixture was Celite-filtered, the filtrate was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate, 10:1) to obtain the title compound (64.4 g, yield: 84percent).

Reference： [1]Patent: EP1733724,2006,A1 .Location in patent: Page/Page column 55

16
[ 454-92-2 ]
[ 29022-11-5 ]
[ 15764-16-6 ]
[ 204316-32-5 ]
[ 439150-41-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5455 - 5461

17
[ 454-92-2 ]
[ 35661-39-3 ]
[ 15764-16-6 ]
[ 204316-32-5 ]
[ 957147-65-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5455 - 5461

18
[ 454-92-2 ]
[ 35661-38-2 ]
[ 15764-16-6 ]
[ 204316-32-5 ]
[ 957147-64-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5455 - 5461

19
[ 15764-16-6 ]
[ 363191-25-7 ]
C₁₈H₂₈N₂O₄ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5455 - 5461

20
[ 15764-16-6 ]
[ 141304-07-6 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; hydroxylamine hydrochloride; In methanol; at 20℃;	A solution of <strong>[15764-16-6]2,4-dimethylbenzaldehyde</strong> (10.0 g; 74.5 mmol), hydroxylamine hydrochloride (7.73 g; 111 mmol) and pyridine (10 mL) in MeOH (75 mL) was stirred at room temperature overnight. The solvent was evaporated and the crude mixture was dissolved in CH2CI2 (150 mL), washed with water (4 x 25 mL) and dried (Na2SO4). The solvent was evaporated to furnish 10.1 g of a transparent oil which solidified at room temperature and was used in the next step. MS m/z 150 [m+1].

Reference： [1]Patent: WO2009/90239,2009,A1 .Location in patent: Page/Page column 19
[2]RSC Advances,2015,vol. 5,p. 90408 - 90421
[3]European Journal of Organic Chemistry,2019,vol. 2019,p. 3190 - 3194
[4]International Journal of Pharmacy and Pharmaceutical Sciences,2019,vol. 11,p. 1 - 7

21
[ 79-24-3 ]
[ 15764-16-6 ]
[ 1006060-12-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With C19H20F2N2O4; neodymium(III) chloride hexahydrate; sodium t-butanolate; In tetrahydrofuran; at -40℃; for 20h;Inert atmosphere; Sealed tube;	General procedure: To a flame dried test tube (20 mL) equipped with a magnetic stirring bar and 3-way glass stopcock was charged with NdCl3?6H2O (4.3 mg, 0.012 mmol), and dried under vacuum at room temperature. Ar was backfilled(evacuation/backfill was repeated for several times) to the test tube, and THF (100 muL) and ligand 1 (200 muL, 0.012 mmol, 0.6 M/THF were added successively by well-dried syringes and needles at room temperature. After stirring the resulting slightly cloudy solution at 60 C for 30 min, NaOtBu (36 muL, 0.072 mmol, 2.0 M/THF) was added dropwise at the same temperature. After stirring the resulting mixture at 60 C for 1 h (white precipitate appeared), the mixture was cooled to room temperature and nitroethane (3) (86 muL, 1.2 mmol) was added (the precipitate was partly dissolved). Self-assembly of Nd/Na catalyst initaiated in a few minutes and the resulting mixture was stirred at room temperature for 12 h to give a thick white suspension. The whole suspension was transferred to an Eppendorf tube and the tube was centrifuged at ca. 104 rpm for 30 sec. The supernatant was decanted and dry THF (1.2 mL) was added to the precipitate. The tube was agitated using a vortex mixer for 30 sec and the resulting tube was centrifuged again, then the supernatant was decanted (washing process). The resulting precipitate was agitated with dry THF (1.6 mL) and the resulting suspension was transferred to a flame-dried 20 mL test tube. After adding nitroethane (3) (286 muL, 4.0 mmol), the mixture was cooled to -40 C and benzaldehyde (2a) (41 muL, 0.4 mmol) was added dropwise. After stirring the reaction mixture at the same temperature for 20 h, 0.2 M AcOH/THF was added and the resulting mixture was extracted with EtOAc (x2). The combined organic layers were washed with sat. aq. NaHCO3, H2O, and brine, and dried over Na2SO4. After removal of volatiles under reduced pressure, the resulting residue was analyzed by 1H NMR to determine diastereomeric ratio of product 4a (anti/syn = >20/1). The crude product was purified by silica gel column chromatography (neutral SiO2 (Kanto Chemical 60N; spherical, 50-60 mumum), eluent: n-hexane/ethyl acetate 8/1) to give 4a (70 mg, 0.38 mmol, 96%). Enantiomeric excess was determined by HPLC analysis [93% ee, DAICEL CHIRALPAK IC (phi 0.46 cm x 25 cm), 2-propanol/n-hexane 1/20, flow rate 1.0 mL/min, detection at 254 nm, tR 11.3 min (anti major-enantiomer: (1R,2S)) and 14.4 min (anti minor-enantiomer: (1S,2R))]. Other runs in Table 3 were operated in a similar manner. DME was used as reaction solvents (after preparation of 6 mol% of the catalyst in THF) in Table 3, entries 8-10.

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 13860 - 13869
[2]Tetrahedron Letters,2016,vol. 57,p. 1815 - 1819

22
[ 15764-16-6 ]
[ 581078-85-5 ]
[ 1241906-84-2 ]

Yield	Reaction Conditions	Operation in experiment
45%	With potassium hydroxide; In methanol; water; at 65℃;	General procedure: Azaaurones were obtained by the condensation of indolinone A (Scheme 1) and substitutedbenzaldehydes [23]. Indolinone A was dissolved in MeOH (10 mL/mmol) and treated with KOH(50% in H2O, 1 mL/mmol). The solution was stirred at room temperature and allowed to reach 65 C progressively. The reaction was quenched when TLC indicated no reaction progression (3 to 24h). The solution was acidified by adding HCl (30 mL, 2 N), evaporated, and the crude was dissolvedin H2O and extracted with ethyl acetate. The organic solution was separated, dried over Na2SO4, and concentrated. The crude mixture was purified by flash chromatography over silica gel, eluted witha mixture of ethyl acetate:cyclohexane (1:2) to aord pure azaaurones. The synthesized compoundswere isolated in 96-98% pure form as evidenced by elemental analysis. For each azaaurone, carbon,hydrogen, and nitrogen atoms were analyzed and were found in nearly full (96-98%) agreementwith the expected values. The compounds were fully characterized by 1H NMR, 13C NMR, andhigh-resolution mass spectrometry (HRMS) (data shown in Supplementary Materials, Table S5).

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 5724 - 5731
[2]Molecules,2020,vol. 25

23
[ 15764-16-6 ]
[ 3478-88-4 ]

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

24
[ 15764-16-6 ]
triethyl phosphonoacetic acid [ No CAS ]
[ 61052-15-1 ]

Yield	Reaction Conditions	Operation in experiment
90%		(62A) Ethyl (2E)-3-(2,4-dimethylphenyl)acrylate Ethyl diethylphosphonoacetate (10.0 g, 44.7 mmol) was dissolved in tetrahydrofuran (100 mL), and sodium hydride (60%, 2.10 g, 55.9 mmol) was added thereto at 0 C., and then, the resulting mixture was stirred under a nitrogen atmosphere for 30 minutes. <strong>[15764-16-6]2,4-Dimethylbenzaldehyd</strong>e (5.00 g, 37.3 mmol) was added thereto at 0 C., and the resulting mixture was stirred under a nitrogen atmosphere for 1 hour. 1 N Hydrochloric acid was added thereto, and the organic matter was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution, then dried over anhydrous magnesium sulfate and filtered. Then, the solvent was distilled off under reduced pressure, whereby a crude product was obtained. This crude product was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 50:50 (v/v)), whereby the objective title compound was obtained as a colorless oily substance (6.87 g, yield: 90%). 1H NMR (CDCl3, 400 MHz): 1.34 (3H, d, J=7.0 Hz), 2.33 (3H, s), 2.41 (3H, s), 4.26 (2H, q, J=7.0 Hz), 6.33 (1H, d, J=16.0 Hz), 7.02 (1H, d, J=8.2 Hz), 7.03 (1H, s), 7.46 (1H, d, J=8.2 Hz), 7.94 (1H, d, J=16.0 Hz)

Reference： [1]Patent: US2011/53974,2011,A1 .Location in patent: Page/Page column 78

25
[ 15764-16-6 ]
[ 77640-03-0 ]
[ 1292769-13-1 ]

Yield	Reaction Conditions	Operation in experiment
92%	With 40% potassium fluoride/alumina In ethanol at 80℃; for 0.166667h; Microwave irradiation;
	In ethyl methyl ether for 2h; Reflux;

Reference： [1]Location in patent: experimental part Feng, Guo-Liang; Zhang, Hong-Li; Geng, Li-Jun; Zhang, Yu-Mei [Journal of Chemical Research, 2011, vol. 35, # 5, p. 302 - 303]
[2]Location in patent: experimental part Feng, Guo-Liang; Zhang, Hong-Li; Geng, Li-Jun [Journal of Chemical Research, 2011, vol. 35, # 2, p. 121 - 123]

26
[ 2234-20-0 ]
[ 50-00-0 ]
[ 15764-16-6 ]

Reference： [1]Catalysis Letters,2011,vol. 141,p. 1355 - 1363

27
[ 15764-16-6 ]
[ 109-77-3 ]
[ 99-07-0 ]
[ 1006703-17-8 ]

Yield	Reaction Conditions	Operation in experiment
89%		General procedure: A stirring mixture of an active carbonyl compound (aldehyde 1 or isatin 7, 1mmol), malononitrile 2 (1.2mmol), magnetic catalytic system ([PEISi-MNPs], 5mg) and ethylene glycol/water (EG/H2O 20/80, 2mL) were sonicated for one minute. To this stirred mixture, an enolizable compounds (3-(dimethylamino)phenol 3, 4-hydroxycoumarin 5 or dimedone 10, 1mmol) was added. The reaction mixture was heated at appropriate temperature as mentioned in Table 1. The progress of the reaction was monitored by TLC. After completion of the reaction (as shown in Tables 2-4), the reaction mixture was allowed to cool at room temperature and diluted with ethyl acetate and the catalyst was easily separated from the reaction mixture with an external magnet and washed twice with ethyl acetate. The combined organic layers were concentrated in vacuum and the residue was purified by crystallization from ethanol. All compounds gave satisfactory spectral data and they were identical with those reported in the literature [29,31-37].

Reference： [1]Journal of Magnetism and Magnetic Materials,2014,vol. 375,p. 217 - 226
[2]Medicinal Chemistry,2011,vol. 7,p. 466 - 472

28
[ 1779-49-3 ]
[ 15764-16-6 ]
[ 2234-20-0 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 11900 - 11903

29
[ 15764-16-6 ]
[ 1811-85-4 ]
[ 150254-19-6 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 11900 - 11903

30
[ 141-84-4 ]
[ 15764-16-6 ]
[ 4818-22-8 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium <i>tert</i>-butylate In ethanol for 19h; Inert atmosphere; Reflux;	3 To a reaction container purged with nitrogen, rhodanine (5.33 g), 2,4-dimethylbenzaldehyde (5.37 g) and ethanol (40 ml) were placed and stirred. tert-Butoxy potassium (1.12 g) and ethanol (20 ml) were added and the mixture was heated under reflux for 19 hours while stirring. The mixture was cooled to room temperature and precipitated crystal was collected by filtration and then subjected to soak cleaning in ethanol to obtain Exemplary Compound No. 28 (8.5 g (yield 85%)) as a slightly yellowish white crystal.

Reference： [1]Current Patent Assignee: HODOGAYA CHEMICAL CO LTD - US2012/315576, 2012, A1 Location in patent: Page/Page column 24

31
[ 75-52-5 ]
[ 15764-16-6 ]
[ 1056474-39-5 ]

Yield	Reaction Conditions	Operation in experiment
84%		General procedure: Method B: A 3.5 M solution of NaOH was dropped into a cooled solution of nitromethane and aromatic aldehyde in methanol at 10C. After the mixture was stirred for 15 min, crushed ice was added until the solid was completely dissolved. The clear solution was dropped into a vigorously stirred solution of 5 M HCl and some solid product appeared. Then the mixture was kept in the refrigerator for another 4 h to generate more solid. The solid product, obtained by filtration, washed with water, dried under vacuum, was finally recrystallized.

Reference： [1]Tetrahedron,2013,vol. 69,p. 4749 - 4757

32
[ 1263324-41-9 ]
[ 15764-16-6 ]
[ 1407708-64-8 ]

Yield	Reaction Conditions	Operation in experiment
66%	With 2,3-diazobicyclo[2.2.1]heptane bis-hydrochloride; In 1,2-dichloro-ethane; at 90℃;	To hydrazine 11 2HCI (2.6 mg, 0.015 mmol, 0.1 equivalent), a solution of <strong>[15764-16-6]2,4-dimethylbenzaldehyde</strong> (40.2 mg, 0.3 mmol, 2 equivalents) was added in 0.5 ml DCE, followed by a solution of cyclopropene 10 (42 mg, 0.15 mmol, 1 equivalent) in 0.25 ml DCE. The reaction was heated to 90C for 48 hours. Upon cooling to room temperature, the reaction mixture was diluted with DCM, washed with 1 M NaOH, extracted into DCM, dried with sodium sulfate, and concentrated. The product was purified by column chromatography on Si (5% EtOAc/hex) to yield the compound as a clear oil (40.6mg, 0.1 mmol, 66% yield). 1H NMR (300 MHz, CDCl3) delta 9.63 (s, 1 H), 7.29-7.34 (m, 1 1 H), 6.96 (m, 2H), 6.66 (d, 1 H, J=16.5Hz), 6.96 (d, 1 H, J=16.5Hz), 4.55 (s, 4H), 3.87 (dd, 4H, J=9.1 Hz), 2.29 (s, 3H), 2.24 (s, 3H); 13C NMR (CDCl3, 75 MHz): 200.79, 138.17, 137.73, 135.19, 133.19, 131 .33, 131 .14, 128.48, 127.75, 126.96, 125.62, 125.18, 73.73, 70.25, 57.95, 21 .18, 19.74; (APCI+) exact mass calculated for C28H31O3+ (MH+) requires m/z 415.22, found m/z 415.13

Reference： [1]Patent: WO2014/22454,2014,A1 .Location in patent: Paragraph 099; 0165

33
[ 15764-16-6 ]
[ 188945-44-0 ]
[ 1499179-46-2 ]

Yield	Reaction Conditions	Operation in experiment
94%		General procedure: Triton B (40% in MeOH, 7.30 mL, 17.5 mmol) was added dropwise to a solution of ethyl 2-[bis(2-isopropylphenoxy) phosphoryl]acetate (5.30 g, 13.1 mmol) in THF (150 mL) at -78 C under Ar. After 15 min of stirring, a solution of 2-methylbenzaldehyde (59) (1.50 g, 12.5 mmol) in THF (50 mL) was added dropwise to the solution. After 10 h of stirring, the mixture was quenched with satd. aq. NH4Cl (30 mL) and extracted with EtOAc (3 x 30 mL). The organic layer was washed successively with H2O, satd. aq. (20 mL) NaHCO3 (20 mL) and brine (20 mL), then dried (MgSO4), filtered and concentratedin vacuo.; Z-selective olefination of <strong>[15764-16-6]2,4-dimethylbenzaldehyde</strong> (95) wasperformed using the procedure described above to provide (Z)-ethyl 3-(2,4-dimethylphenyl)acrylate (cis-151) (94%, Z only, determinedby 1H-NMR spectrum) (silica gel CC, EtOAc/hexane, 10:90)as a colorless oil: 1H-NMR (CDCl3, 270 MHz) d: 1.18 (t, J = 7.0 Hz,3H, -CH3), 2.25, 2.31 (s, each 3H, Ar-CH3), 4.10 (q, J = 7.0 Hz, 2H,-CH2-), 5.97 (d, J = 12.2 Hz, 1H, CH-CO2-), 6.95-6.99 (m, 2H,Ar-H), 7.08 (d, J = 12.2 Hz, 1H, Ar-CH), 7.26 (d, J = 7.8 Hz, 1H,Ar-H).

Reference： [1]Phytochemistry,2013,vol. 96,p. 132 - 147

34
[ 134-32-7 ]
[ 542-92-7 ]
[ 15764-16-6 ]
cis-6-(2,4-dimethylphenyl)-6,6a,7,9a-tetrahydro-5H-benzo[h]cyclopenta[c]quinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With ytterbium(III) triflate; In toluene; at 50℃; for 0.666667h;Sonication; Irradiation; Inert atmosphere;	General procedure: For the ultrasound-assisted method, a mixture of Yb(OTf)3 (12.4mg, 0.02mmol), aryl amine (1.00mmol), aromatic aldehyde (1.00mmol) and freshly distilled cyclopentadiene or 1,3-cyclohexadiene (3.00mmol) in dry PhMe (3.00mL) was irradiated with ultrasound of low power (with a frequency of 35kHz and a nominal power of 230W) at 50C under a nitrogen atmosphere for 40min. The reaction flask was located at the maximum energy area in the cleaner and the surface of the reactants was placed slightly lower than the level of the water. The addition or removal of water controlled the temperature of the water bath. After completion of the reaction, as indicated by TLC monitoring, the reaction mixture was diluted with water (10mL) and extracted with ethyl acetate (3×10mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in a vacuum. The resulting product was purified by column chromatography over silica gel to afford the corresponding tetrahydroquinolines and hexahydrophenanthridines.

Reference： [1]Ultrasonics Sonochemistry,2014,vol. 21,p. 1600 - 1607

35
[ 15764-16-6 ]
[ 135-19-3 ]
[ 37097-00-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With vanadatesulfuric acid; In neat (no solvent); at 80℃; for 0.416667h;	General procedure: In a round-bottomed flask the aldehyde (1mmol),2-naphthol (2 mmol) and VSA (10 mol%) were mixed thoroughly. The flask was heated at 80 C with concomitant stirring. After completion of the reaction confirmed by TLC(eluent: EtOAc:n-hexane, 1:4), hot ethanol (10 mL) was added and filtered and separated solid catalyst. The solvent was evaporated and the crude products were recrystallized from ethanol, gave the pure products in 80-93% yields based on thestarting aldehyde (Table 2). The products were characterized by IR, 1H NMR, 13C NMR and via comparison of their melting points with the reported ones.
79%	With Nano alumina sulfuric acid; In neat (no solvent); at 120℃; for 0.166667h;Green chemistry;	General procedure: Nano-alumina sulfuric acid (0.05 g) was added to a mixtureof various aromatic aldehydes (1 mmol) and -naphthol(2 mmol, 0.288 g) which then heated at 120C in an oil bathwith stirring for appropriate time. After completion of thereaction, scrutinized by TLC (n-hexane: ethyl acetate = 5:2),hot ethanol was added and through a simple filtration, thecatalyst was extracted from the reaction mixture. Then, theobtained liquid evaporated gradually in the ambient temperatureto give the crude product by recrystallization from ethanol.The characteristics of the all known products were studiedby 1H NMR, 13C NMR, IR and melting points and werecompared with the reported ones in previous studies.

Reference： [1]Revue Roumaine de Chimie,2013,vol. 58,p. 27 - 35
[2]Letters in Organic Chemistry,2016,vol. 13,p. 58 - 66
[3]Letters in Organic Chemistry,2016,vol. 13,p. 58 - 66

36
[ 1618092-42-4 ]
[ 15764-16-6 ]
[ 1618092-44-6 ]

Yield	Reaction Conditions	Operation in experiment
72%		General procedure: 4.2.7. (4R)-4-Methyl-4-[(E)-2-phenylethenyl]-1,3-oxazolidin-2-one(9a) and (4S)-4-(diphenylphosphorylmethyl)-4-methyl-oxazolidin-2-one (13eo). Typical procedure of a Wittig reaction: To a suspensionof the phosphonium salt (13) (500 mg, 1.0 mmol, 2.0 equiv) in THF(5 mL) was added n-butyllithium (1.9 M in hexane, 1.0 mL,1.95 mmol, 3.9 equiv) at 78 C and then the solution was stirredfor 30 min at the same temperature. After the addition of benzaldehyde(54 mg, 0.5 mmol,1.0 equiv) at 78 C, the reaction mixturewas gradually warmed to ambient temperature and stirred for 2 h.After quenching with saturated aq NH4Cl (10 mL), the resultingbiphasic mixture was extracted with AcOEt (10 mL2). The combinedorganic layer was washed with water (10 mL) and brine(10 mL), dried over Na2SO4, filtered, and evaporated. Purification bysilica gel column chromatography (hexane:AcOEt3:1 to 1:1)provided 9a (101 mg, 99% yield, 98.6% ee) as a white solid, and 13-o(156 mg, 99% yield) as a white solid. The enantiomeric excess of 9awas determined by HPLC analysis by using the following condition.DAICEL CHIRALCEL IA column (4.6f150 mm), hexane:EtOH95:5(0 min)d50:50 (8.0 min), flow rate: 2.0 ml/min, temperature:25.0 C. The retention times of (S)-9a and (R)-9a were 4.6 min and5.3 min, respectively. (Compound 9a) mp: 155.6 C; [a]D20 61.0 (c0.27, CH3OH); 1H NMR (500 MHz, CDCl3) d ppm: 1.53 (s, 3H), 4.17 (d,1H, J8.3 Hz), 4.23 (d, 1H, J8.3 Hz), 5.09 (s, 1H), 6.21 (d, 1H,J16.1 Hz), 6.59 (d, 1H, J16.1 Hz), 7.26e7.36 (m, 5H); 13C NMR(126 MHz, CDCl3) d ppm; 25.6, 58.5, 76.5, 126.7, 128.3, 128.7, 130.1,131.2, 135.7, 159.0; IR (KBr) cm1: 3293, 1756, 1710, 1393, 1288, 1171,1042, 967, 751, 659; MS (ESI) m/z: 203 (M); Anal. Calcd forC12H13NO2: C, 70.92; H, 6.45; N, 6.89. Found: C, 70.80; H, 6.49; N,6.83. (Compound 13-o) mp: 181.4 C; [a]D20 9.1 (c 0.41, CH3OH); 1HNMR (500 MHz, CDCl3) d ppm: 1.34 (s, 3H), 4.09 (d, 1H, J8.8 Hz), 2.60e2.78 (m, 2H), 4.21 (d, 1H, J8.8 Hz), 6.44 (br s, 1H), 7.46e7.57(m, 5H), 7.67e7.71 (m, 2H), 7.78e7.82 (m, 2H); 13C NMR (126 MHz,CDCl3) d ppm; 26.7, 39.9 (d, J69.1 Hz), 57.3 (d, J4.8 Hz), 77.4 (d,J12.5 Hz), 128.9 (d, J3.6 Hz), 129.0 (d, J3.6 Hz), 130.3 (d,J9.5 Hz), 130.6 (d, J9.5 Hz), 132.2, 132.3, 132.8 (d, J90.6 Hz),133.6 (d, J93.0 Hz), 157.7; IR (KBr) cm1: 3308, 1758, 1439, 1255,1175, 1034, 930, 752, 699; HRMS (ESI): calcd for C17H19NO3P[MH] 316.1103; found 316.1105
72%		General procedure: Typical procedure of a Wittig reaction: To a suspension of the phosphonium salt (13) (500 mg, 1.0 mmol, 2.0 equiv) in THF(5 mL) was added n-butyllithium (1.9 M in hexane, 1.0 mL,1.95 mmol, 3.9 equiv) at 78 C and then the solution was stirred for 30 min at the same temperature. After the addition of benzaldehyde(54 mg, 0.5 mmol,1.0 equiv) at 78 C, the reaction mixture was gradually warmed to ambient temperature and stirred for 2 h. After quenching with saturated aq NH4Cl (10 mL), the resulting biphasic mixture was extracted with AcOEt (10 mL2). The combined organic layer was washed with water (10 mL) and brine(10 mL), dried over Na2SO4, filtered, and evaporated. Purification bysilica gel column chromatography (hexane:AcOEt3:1 to 1:1)provided 9a (101 mg, 99% yield, 98.6% ee) as a white solid, and 13-o(156 mg, 99% yield) as a white solid.

Reference： [1]Tetrahedron,2014,vol. 70,p. 5234 - 5241
[2]Tetrahedron,2014,vol. 70,p. 5234 - 5241

37
[ 110-89-4 ]
[ 15764-16-6 ]
[ 536-74-3 ]
N-[1-(2,4-dimethylphenyl)-3-phenyl-2-propynyl]piperidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With N,N'-ethylenebis(salicylideneiminato)copper(II); In neat (no solvent); at 80℃; for 3h;	General procedure: In a 5-ml round-bottomed flask containing Cu(salen) (0.01g, 3 mol%) in air, aldehyde (1 mmol), amine (1.2 mmol), and phenylacetylene (1.5 mmol) were added. The flask was then stoppered and the mixture was stirred at 80 C (oil bath temperature).The completion of the reaction was monitored byTLC or GC. After reaction completion and cooling to room temperature,diethyl ether (5 ml) was added and the Cu salen wasremoved by filtration. The solvent was evaporated under reducedpressure, and the residue was purified by flash columnchromatography on silica gel (eluent: hexane/ethyl acetate =10) to give the corresponding product.

Reference： [1]Cuihua Xuebao/Chinese Journal of Catalysis,2013,vol. 34,p. 2217 - 2222
[2]New Journal of Chemistry,2015,vol. 39,p. 1827 - 1839

38
[ 1380503-26-3 ]
[ 15764-16-6 ]
2-(2,4-dimethylbenzoyl)-1-(pyrimidin-2-yl)-1H-indole-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With tert.-butylhydroperoxide; palladium diacetate; In decane; ethyl acetate; at 125℃; for 24h;Inert atmosphere;	General procedure: To a 25-mL sealed tube were added indole (0.3 mmol), aldehyde (0.45 mmol), Pd(OAc)2 (6.72 mg,10 mmol%), TBHP (anhydrous, about 5M in decane) (4 equiv), EtOAc (2.0 mL). The tube wascapped and stirred under N2 at 125 C for 24 h. The reaction mixture was cooled to roomtemperature and diluted with CH2Cl2, filtered through a short pad of Celite, washed with brine andCH2Cl2 .The combined organic extracts were dried over Na2SO4, concentrated in vacuum, and theresulting residue was purified by silica gel column chromatography to afford the desired product.All compounds are characterized by 1H NMR, 13C NMR, LRMS/HRMS and their comparison toliterature values

Reference： [1]Synlett,2015,vol. 26,p. 771 - 778

39
[ 4783-68-0 ]
[ 15764-16-6 ]
(2,4-dimethylphenyl)(2-(pyridin-2-yloxy)phenyl)methanone [ No CAS ]

Reference： [1]Organometallics,2015,vol. 34,p. 953 - 966

40
[ 4885-02-3 ]
[ 108-38-3 ]
[ 21945-76-6 ]
[ 15764-16-6 ]
[ 1123-56-4 ]

Yield	Reaction Conditions	Operation in experiment
9.9%		General procedure: The appropriate benzene derivative (3.2-10.6 mmol) was dissolved in dry DCM (10-20 mL), purged with Ar, and cooled with an ice bath to 0 C. Next, TiCl4 (2.2 eq.) was added dropwise. The reaction mixture was stirred for 1 h. Afterwards, dichloromethyl methyl ether (1.1 eq.) was added, and the mixture was left to react for a further 45 min. As a reaction quencher, a saturated solution of NH4Cl (25 mL) was added. The mixture was then left for 2 h. The organic layer was separated and washed with 0.1 N HCl solution (3 × 50 mL) and brine (3 × 50 mL). The organic layer was dried over MgSO4 and filtered, and the solvent was evaporated under vacuum to furnish the desired aldehydes (Figure 1). The purified products were homogeneous by HPLC and were characterized and purified by using various physical techniques.

Reference： [1]Molecules,2015,vol. 20,p. 5409 - 5422

41
[ 3300-51-4 ]
[ 118-92-3 ]
[ 15764-16-6 ]
2-(2,4-dimethylphenyl)-3-(4-(trifluoromethyl)benzyl)quinazolin-4(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In ethyl acetate; at 20℃; for 4h;	General procedure: To a solution of anthranilic acid (1 mmol) in ethyl acetate (3 ml) solvent, triethyl amine (1.5 mmol) and T3P (2 mmol) was added and the resulting reaction mixture was stirred at room temperature for 1-2 hrs. The reaction was monitored by TLC, aldehyde (1 mmol) was added and stirred for 1-2 hrs. DDQ (1 mmol) was added to the reaction mixture and further stirred for 30 mins. After completion of the reaction, the mixture is diluted with (20 ml) water and neutralized with 10% NaHCO3 solution. The product was extracted with ethyl acetate (10 ml) and the combined organic phase was washed with water (10ml) and brine solution. The organic phase was dried over anhydrous Na2SO4. The solvent was dried under reduced pressure to afford a crude product, which was purified on silica gel using ethyl acetate and petroleum ether.

Reference： [1]Chinese Chemical Letters,2015,vol. 26,p. 963 - 968

42
[ 15764-16-6 ]
[ 28144-70-9 ]
2-(2,4-dimethylphenyl)-2,3-dihydroquinazolin-4(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With sulphonic acid functionalised Wang resin; In water; at 100℃; for 0.5h;Green chemistry;	General procedure: A mixture of 2-aminobenzamide 1 (1 mmol) and aldehyde 2 (2a-2v) or ketone 4 (1.2 mmol) was dissolved in 5 ml of water and Wang-OSO3H (10% w/w) was added under stirring condition at 100 C. Stirring was continued in for the stipulated period of time (Table 5). The progress of the reaction was monitored with TLC. After completion of the reaction, the reaction mixture was diluted with 1:9 mixture of methanol/ethyl acetate to dissolve the precipitated product and the catalyst was removed simply by filtration. The residual catalyst was repeatedly washed with ethyl acetate (35 volumes). The combined filtrate and washings, on evaporation, gave the desired product. This was further purified by column chromatography using silica gel (60-120 mesh) with ethyl acetate and hexane (4:6) as eluent to afford the desired product 3 (3a-3v) or 5.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 4714 - 4717

43
[ 645-00-1 ]
[ 15764-16-6 ]
4-methyl-2-(3-nitrobenzyl)benzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With palladium(II) trifluoroacetate; (S)-2-amino-N-(1-hydroxy-2-methylpropan-2-yl)-3-phenylpropanamide; silver trifluoroacetate; acetic acid; In water; at 90℃; for 12h;	General procedure: O-Tolualdehyde (0.24 mmol), iodobenzene (0.2 mmol), silver trifluoroacetate (0.3 mmol, 66 mg), palladium trifluoroacetate (0.02 mmol, 7 mg), Phe-Me2AA ligand (0.08 mmol, 19 mg), acetic acid (1.8 mL) and H2O (0.2 mL) were added to a vial. The mixture was heated to 90 C for 12 h. The reaction mixture was allowed to cool to room temperature and filtered through a silica gel pad, concentrated in vacuum. The desired product was isolated by a silica gel column chromatography or preparative TLC.

Reference： [1]Science,2016,vol. 351,p. 252 - 256
[2]Tetrahedron,2018,vol. 74,p. 2048 - 2055

44
[ 15764-16-6 ]
[ 73258-94-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With C17H17BrClN2RuSe(1+)*F6P(1-); hydroxylamine hydrochloride; sodium hydroxide; In toluene; at 100℃; for 12h;	General procedure: In an oven-dried 100mL two-neck round bottom flask, amixture of aryl-aldehyde (1.0 mmol), NH2OH.HCl (1.0 mmol), NaOH (1.0 mmol), catalyst (0.1 mol%) and solvent (5 ml) were heated at 100 C with continuous stirring for 12 h in air. The progress of the reaction was continuously monitored by TLC until the maximum conversion of an aldehyde to the desired product observed. After completion, the reaction mixture was cooled to room temperature and extracted in ethyl acetate (2 25 mL). This extract was further washed with water and dried over anhydrous Na2SO4. The product was purified by column chromatography after removing the solventon a rotary evaporator under reduced pressure. All the desired product obtained as white solid was authenticated by HR-MS, 1H,and 13C{1H} NMR spectroscopy.

Reference： [1]Journal of Organometallic Chemistry,2019,vol. 879,p. 69 - 77
[2]New Journal of Chemistry,2016,vol. 40,p. 1626 - 1632

45
[ 141-97-9 ]
[ 15764-16-6 ]
3-methyl-4-(2,4-dimethylphenyl)methylene-isoxazole-5(4H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With Ag/SiO2; hydroxylamine hydrochloride; In water; at 20℃; for 1h;Green chemistry;	General procedure: To equimolar ratios of hydroxylamine (1.1 mmol), ethylacetoacetate (1 mmol) and aldehyde (1 mmol) dissolved in water (10 ml) at room temperature (RT) using Ag/SiO2 (30 mg) as catalyst. The reaction mixture was stirred continuously for 1 h at RT, (Scheme 1) using a magnetic stirrer. The progress of the reaction was monitored by thin-layer chromatography (TLC). The reaction mixture was then filtered, and the filtrate was subsequently extracted with ethyl acetate and evaporated under reduced pressure to obtain the crude product. Further, the crude product was purified with a 4:6 ratio of EtOAc:Hexane mobile solvent to afford pure products (4a-m). The recovered catalyst was subjected to washing with ethanol, dried, and could be reused for up to seven cycles.
91%	With N,N,N?,N?-tetramethyl-N,N?-bis(sulfo)ethane-1,2-diaminium mesylate; hydroxylamine hydrochloride; at 70℃; for 0.666667h;	General procedure: A mixture of ethyl acetoacetate (1 mmol, 0.130 g), hydroxylamine hydrochloride (1.2 mmol, 0.083 g) and [TMBSED][OMs]2 (0.1 mmol, 0.047 g) was stirred at 70 C for 1 min. Then, aldehyde (1 mmol) was added to it, and the resulting mixture was stirred at the same temperature. After the reaction was completed (as monitored by TLC), the mixture was cooled to room temperature, and the resulting precipitate was washed by water (2 x 2 mL), dried under vacuum, and recrystallized from methanol to give the pure product.

Reference： [1]Research on Chemical Intermediates,2016,vol. 42,p. 2553 - 2566
[2]Research on Chemical Intermediates,2018,vol. 44,p. 6253 - 6266

46
[ 15764-16-6 ]
[ 137-07-5 ]
[ 902086-26-4 ]

Yield	Reaction Conditions	Operation in experiment
81%	With air; In dimethyl sulfoxide; at 60℃; for 6h;	General procedure: 2-Aminothiophenol (0.5 mmol; 1.0 equiv) and aromatic aldehydes (0.6 mmol; 1.2 equiv)were dissolved in DMSO (3 mL). Then, the reaction mixture was stirred at 60 C for 6 h. Afterthe reactionH2O was added to the mixture. The mixture was extracted with AcOEt (20 mL x 3).The combined organic layers were then washed with saturated aq. NaCl (30 mL). The solutionwas dried with anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude residue waspurified with silica gel chromatography (AcOEt- PE130) to give pure product.

Reference： [1]Synlett,2016,vol. 27,p. 1387 - 1390

47
[ 696-62-8 ]
[ 15764-16-6 ]
2-(4-methoxybenzyl)-4-methylbenzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With 3 wt% Pd/gamma-Al2O3; silver trifluoroacetate; acetic acid hydrazide; In acetic acid; at 130℃; for 48h;	General procedure: In a typical reaction, o-methyl benzaldehyde(0.10 mmol), iodobenzene (0.30 mmol), acetohydrazide (0.03 mmol), silver trifluoroacetate (0.30 mmol), catalyst(25 mg), and the solvent AcOH : HFIP =3:1 (2.0 mL) were charged in a 25 mL oven dried reaction tube. Reactionwas carried out 130 for 48 h in an oil bath under air condition. After being cooled to room temperature, thereaction solution was evaporated in vacuo. The residue was purified by flash column chromatography (silica gel,ethyl acetate/petroleum ether = 1:15~1:30 as an eluent) to afford the desired product 3. All the products were alsoconfirmed by comparing the 1H NMR and 13C NMR data with authentic samples.
	With silver(I) acetate; palladium diacetate; acetic acid hydrazide; In water; acetic acid; at 110℃; for 24h;	General procedure: A flask (10 mL) with magnetic stir bar was charged with s1 (1.2 equiv.), s2 (1 equiv.), Pd(OAc)2 (0.1 equiv.), acetohydrazide (0.2 equiv.), AgOAc (2 equiv.), AcOH (5 mL) and H2O (5 mL). Theflask was allowed to stir at r.t. for 20 minutes, and then heated to 110 C for 24 hours. After completion of the reaction, the mixture was cooled to r.t., filtered and concentrated in vacuum.The crude reaction mixture was purified by silica gel column chromatography to afford the corresponding aldehyde s3.5

Reference： [1]Organic Letters,2016,vol. 18,p. 2708 - 2711
[2]Advanced Synthesis and Catalysis,2020,vol. 362,p. 133 - 138
[3]Chinese Chemical Letters,2020
[4]Synthetic Communications,2020
[5]Synthesis,2017,vol. 49,p. 1884 - 1888

48
[ 15764-16-6 ]
[ 109-77-3 ]
[ 591-24-2 ]
2-amino-4-(2,4-dimethylphenyl)-7-methyl-5,6,7,8-tetrahydronaphthalene-1,3-dicarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium hydroxide; In water; at 20℃; for 0.25h;Sonication; Green chemistry;	General procedure: A 100-mL reaction flask was charged with aromatic aldehyde (1.0 mmol) and malononitrile (2.0 mmol) in water (10 mL), and the mixture was exposed to sonification for 15 min at room temperature followed by addition of 3-methylcyclohexanone/2-methyl-cyclohexanone (1.0 mmol) and sodium hydroxide solution (1 mmol in 10 mL water) (Scheme 1). The reaction flask was placed in an ultrasonic bath, where the surface of reactants is slightly lower than the level of water, and the reaction mixture was irradiated under sonication at room temperature. Reaction progress was monitored by thin layer chromatography (TLC). The crude product was filtered and washed with water followed by drying under vacuum.

Reference： [1]Research on Chemical Intermediates,2016,vol. 42,p. 8097 - 8108

49
[ 118-48-9 ]
[ 15764-16-6 ]
2-(2,4-dimethylphenyl)-2,3-dihydroquinazolin-4(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With titanium silicon oxide; ammonium acetate; In water; at 100℃; for 3h;Green chemistry;	General procedure: A mixture of isatoic anhydride, aromatic aldehyde, primary amine or ammonium acetate, titanium silicon oxide nanopowder in water (5 ml) was stirred at 100C for 2-6 h. After completion of the reaction as indicated by TLC, cooled to room temperature, ethyl acetate (30 ml) was added and filtered, washed the catalyst with additional ethyl acetate (10 ml). The filtrate was collected and the layers were separated, organic layer was concentrated under reduced pressure to get crude product, which was further purified by silica-gel column chromatography (hexane-EtOAc, 3:2) to afford the desired product.

Reference： [1]Synthetic Communications,2017,vol. 47,p. 121 - 130

50
1-(4-hydroxy-3-methylbenzofuran-5-yl)-2-(methylsulfinyl)ethan-1-one [ No CAS ]
[ 15764-16-6 ]
2-(2,4-dimethylphenyl)-9-methyl-4H-furo[2,3-h]chromen-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With pyrrolidine; In benzene; at 110℃; for 3h;	<strong>[15764-16-6]2,4-dimethylbenzaldehyde</strong> and tetrahydropyrrole were uniformly dispersed in benzene so that the molar ratio of <strong>[15764-16-6]2,4-dimethylbenzaldehyde</strong> and tetrahydropyrrole was 1: 2: 0.5, corresponding to the reaction solvent per milliliter Of the feed amount was 0.02 g to obtain a raw material mixture. The raw material mixture was reacted at 110 C for 3 hours,The solvent was distilled off and the crude product was recrystallized from ethanol to give the pure product. The obtained flavonoid derivatives are: 2- (2,4-Dimethyl-phenyl) -9-methyl-4H-furan [2,3-h] benzopyran-4-one, yield 89%

Reference： [1]ChemistryOpen,2017,vol. 6,p. 102 - 111
[2]Patent: CN106336416,2017,A .Location in patent: Paragraph 0109; 0110; 0111; 0112; 0113; 0114

51
[ 103989-65-7 ]
[ 15764-16-6 ]
(E)-3-(2,4-dimethylphenyl)-1-(4-hydroxy-3-methylbenzofuran-5-yl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%		Under the protection of nitrogen, the intermediate 1 - (4 - hydroxy -3 - methyl benzofuran -5 - yl) ethyl -1 - one uniformly dispersed in the in tetrahydrofuran, at room temperature, then adding hydrogenated potassium, stirring 15 minutes. Then in the system by adding 2, 4 - dimethyl benzaldehyde tetrahydrofuran solution, finishing the adding to keep the system at room temperature, stirring the reaction 2 hours, then added to the system in the two times the volume of the solvent water quenching reaction, for the system to adjust to the hydrochloric acid. Filtering the separated crude product, the crude product using ethanol to recrystallize the pure product can be obtained. In the step 1 - (4 - hydroxy -3 - methyl benzofuran -5 - yl) ethyl -1 - one with 2, 4 - dimethyl benzaldehyde and sodium hydride in a molar ratio of 1:5: 5, corresponding to each milliliter of reaction solvent inventory 0.045g. The resulting furan chalcone derivatives is: (E)-3 - (2, 4 - dimethyl phenyl) -1 - (4 - hydroxy -3 - methyl benzofuran -5 - yl) -2 - propylene -1 - one, yield 85%, the derivatives of the structure is: Molecular formula: C20 H18 O3 Chinese-named: (E)-3 - (2, 4 - dimethyl phenyl) -1 - (4 - hydroxy -3 - methyl benzofuran -5 - yl) -2 - propylene -1 - ketone English name: (E)-3 - (2,4 - dimethylphenyl) -1 - (4 - hydroxy - 3 - methylbenzofuran - 5 - and the window) prop - 2 - en of the - 1 - the one Molecular weight: 306.13 Appearance: dark yellow solid

Reference： [1]ChemistryOpen,2017,vol. 6,p. 102 - 111
[2]Patent: CN106243121,2016,A .Location in patent: Paragraph 0202-0211

52
[ 15764-16-6 ]
[ 109-77-3 ]
[ 4860-93-9 ]
6-amino-4-(2,4-dimethylphenyl)-3-phenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: 2,4-dimethylbenzaldehyde; malononitrile With triethylamine In ethanol at 80℃; for 0.0333333h; Stage #2: 3-phenyl-1H-pyrazol-5-one In ethanol at 80℃; for 0.25h;

Reference： [1]Qvortrup, Katrine; Jensen, Jakob F.; Sørensen, Mikael S.; Kouskoumvekaki, Irene; Petersen, Rasmus K.; Taboureau, Olivier; Kristiansen, Karsten; Nielsen, Thomas E. [PLoS ONE, 2017, vol. 12, # 2]

53
[ 55984-93-5 ]
[ 15764-16-6 ]
C₁₇H₁₇NO [ No CAS ]
C₁₇H₁₇NO [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 3807 - 3810

54
methyl 3-(4-hydroxy-3-methylbenzofuran-5-yl)-3-oxopropanoate [ No CAS ]
[ 15764-16-6 ]
methyl 2-(2,4-dimethylphenyl)-3-fluoro-9-methyl-4-oxo-3,4-dihydro-2H-furo[2,3-h]chromene-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%		Under a nitrogen atmosphere, methyl 3- (4-hydroxy-3-methylbenzofuran-5-yl)-3-pyruvate and <strong>[15764-16-6]2,4-dimethylbenzaldehyde</strong> were uniformly dispersed in absolute ethanol ; Then adding L-proline, Stirring at 55 C for 12 h; adding anhydrous sodium carbonate and N-fluorobisbenzenesulfonamide to the system, Reaction 12h; and then add twice the volume of water in the water quenching reaction; filtration system, The resulting solid is the crude product, the crude product is washed with water to obtain the pure product, In the reaction system, methyl 3- (4-hydroxy-3-methylbenzofuran-5-yl) -3-pyruvate is reacted with <strong>[15764-16-6]2,4-dimethylbenzaldehyde</strong>, The molar ratio of L-proline, anhydrous sodium carbonate and N-fluorobisbenzenesulfonamide is 1: 1: 0.5: 2: 2; The amount of methyl 3- (4-hydroxy-3-methylbenzofuran-5-yl) -3-pyruvate per milliliter of absolute ethanol was 0.06 g; The resulting benzofuran fluoro-flavanone derivatives are: 2- (2,4-dimethylphenyl) -3-fluoro-9-methyl-4-oxo-3,4-dihydro-2H-furan [2,3-h] benzopyran- - carbonate, yield 87%, the structure of the derivative:

Reference： [1]Patent: CN106905340,2017,A .Location in patent: Paragraph 0102-0107; 0109

55
[ 79887-10-8 ]
[ 1670-14-0 ]
[ 15764-16-6 ]
4-(2,4-dimethylphenyl)-6-(4-pentylphenyl)-2-phenylpyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With potassium tert-butylate; In dimethyl sulfoxide; at 120℃; for 12h;Inert atmosphere;	0.20 mmol of benzamidine hydrochloride was added to the test tube,0.25 mmol of 4-pentylphenylacetylene,0.25 millimoles of <strong>[15764-16-6]2,4-dimethylbenzaldehyde</strong>,0.4 mmol of potassium tert-butoxide,1 ml of dimethyl sulfoxide,Under nitrogen protection conditions,At 120 CThe reaction was stirred for 12 hours,Stop heating and stirring,Cool to room temperature.Ethyl acetate extraction reaction solution,The solvent was removed by distillation under reduced pressure,And then purified by column chromatography,Get the target product,The column chromatography eluent used was in a volume ratio of 300: 1Of petroleum ether:Ethyl acetate mixed solvent,The yield was 64%.

Reference： [1]Patent: CN106674131,2017,A .Location in patent: Paragraph 0112; 0113; 0114; 0115; 0116; 0117; 0118-0121
[2]Journal of Organic Chemistry,2017,vol. 82,p. 13609 - 13616

56
[ 1670-14-0 ]
[ 15764-16-6 ]
[ 766-97-2 ]
4-(2,4-dimethylphenyl)-2-phenyl-6-(p-tolyl)pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With potassium tert-butylate; In dimethyl sulfoxide; at 120℃; for 12h;Inert atmosphere;	0.20 mmol of benzamidine hydrochloride was added to the test tube,0.25 mmol of 4-methylphenylacetylene,0.25 millimoles of <strong>[15764-16-6]2,4-dimethylbenzaldehyde</strong>,0.4 mmol of potassium tert-butoxide,1 ml of dimethyl sulfoxide,Under nitrogen protection conditions,At 120 CThe reaction was stirred for 12 hours,Stop heating and stirring,Cool to room temperature.Ethyl acetate extraction reaction solution,The solvent was removed by distillation under reduced pressure,And then purified by column chromatography,Get the target product,The column chromatography eluent used was in a volume ratio of 500: 1Of petroleum ether:Ethyl acetate mixed solvent,The yield was 63%.

Reference： [1]Patent: CN106674131,2017,A .Location in patent: Paragraph 0122; 0123; 0124; 0125; 0126; 0127; 0128-0131
[2]Journal of Organic Chemistry,2017,vol. 82,p. 13609 - 13616

57
[ 766-83-6 ]
[ 1670-14-0 ]
[ 15764-16-6 ]
4-(3-chlorophenyl)-6-(2,4-dimethylphenyl)-2-phenylpyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With potassium tert-butylate; In dimethyl sulfoxide; at 120℃; for 12h;Inert atmosphere;	In the screw test tube to join0.20 mmol of benzamidine hydrochloride,0.25 mmol 3-chlorophenylacetylene,0.25 millimoles of <strong>[15764-16-6]2,4-dimethylbenzaldehyde</strong>,0.4 mmol of potassium tert-butoxide,1 ml of dimethyl sulfoxide,Under nitrogen protection conditions,The reaction was stirred at 120 C for 12 hours,Stop heating and stirring,Cool to room temperature.Ethyl acetate extraction reaction solution,The solvent was removed by distillation under reduced pressure,And then purified by column chromatography,Get the target product,The column chromatography eluent used was in a volume ratio of 100: 1Of the petroleum ether: BEthyl acetate mixed solvent,The yield was 59%.

Reference： [1]Patent: CN106674131,2017,A .Location in patent: Paragraph 0132; 0133; 0134; 0135; 0136; 0137; 0138-0141
[2]Journal of Organic Chemistry,2017,vol. 82,p. 13609 - 13616

58
[ 873-73-4 ]
[ 1670-14-0 ]
[ 15764-16-6 ]
4-(4-chlorophenyl)-6-(2,4-dimethylphenyl)-2-phenylpyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With potassium tert-butylate; In dimethyl sulfoxide; at 120℃; for 12h;Inert atmosphere;	0.20 mmol of benzamidine hydrochloride, 0.25 mmol of 4-chlorophenylacetylene, 0.25 mmol<strong>[15764-16-6]2,4-dimethylbenzaldehyde</strong>, 0.4 mmol of potassium tert-butoxide, 1 ml of dimethyl sulfoxide,Under the nitrogen protection strip,Stir at 120 CMix reaction for 12 hours,Stop heating and stirring,Cool to room temperature.Ethyl acetate extraction reaction solution,The solvent was removed by distillation under reduced pressure,And then purified by column chromatography,Get the target product,The column chromatography eluent used was in a volume ratio of 500: 1Of the petroleum ether: BEthyl acetate mixed solvent,The yield was 57%.

Reference： [1]Patent: CN106674131,2017,A .Location in patent: Paragraph 0142; 0143; 0144; 0145; 0146; 0147; 0148-0151
[2]Journal of Organic Chemistry,2017,vol. 82,p. 13609 - 13616

59
[ 767-91-9 ]
[ 1670-14-0 ]
[ 15764-16-6 ]
4-(2,4-dimethylphenyl)-6-(2-methoxyphenyl)-2-phenylpyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With potassium tert-butylate; In dimethyl sulfoxide; at 120℃; for 12h;Inert atmosphere;	0.20 mmol of benzamidine hydrochloride was added to the test tube,0.25 millimoles of 2-methoxyphenylacetylene,0.25 millimoles of <strong>[15764-16-6]2,4-dimethylbenzaldehyde</strong>,0.4 mmol of potassium tert-butoxide,1 ml of dimethyl sulfoxide,Under nitrogen protection conditions,At 120 CThe reaction was stirred for 12 hours,Stop heating and stirring,Cool to room temperature.Ethyl acetate extraction reaction solution,Remove the solvent by steaming under reduced pressureAnd then purified by column chromatography,Get the target product,The column chromatography elution was used in a volume ratio of 60: 1Of the oilEther: ethyl acetate mixed solvent,The yield was 57%.

Reference： [1]Patent: CN106674131,2017,A .Location in patent: Paragraph 0152; 0153; 0154; 0155; 0156; 0157; 0158-0161
[2]Journal of Organic Chemistry,2017,vol. 82,p. 13609 - 13616

60
[ 1670-14-0 ]
[ 15764-16-6 ]
[ 536-74-3 ]
4-(2,4-dimethylphenyl)-2,6-diphenylpyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With potassium tert-butylate; In dimethyl sulfoxide; at 120℃; for 12h;Inert atmosphere;	In the screw test tube to join0.20 mmol of benzamidine hydrochloride,0.25 millimoles of phenylacetylene,0.25 millimoles <strong>[15764-16-6]2,4-dimethylbenzaldehyde</strong>,0.4 mmol of potassium tert-butoxide,1 ml of dimethyl sulfoxide,Under nitrogen protection conditions,Stirred at 120 CShould be 12 hours,Stop heating and stirring,Cool to room temperature.Ethyl acetate extraction reaction solution,The solvent was removed by distillation under reduced pressure,And then throughColumn chromatography separation and purification,Get the target product,The column chromatography eluent used was in a volume ratio of 100: 1Of petroleum ether: ethyl acetate mixed solvent,The yield was 73%.

Reference： [1]Patent: CN106674131,2017,A .Location in patent: Paragraph 0040; 0041; 0042; 0043; 0044; 0045; 0046-0061
[2]Journal of Organic Chemistry,2017,vol. 82,p. 13609 - 13616

61
[ 21667-62-9 ]
[ 15764-16-6 ]
[ 56062-81-8 ]
(5-amino-4-(3-chlorobenzoyl)-3-(2,4-dimethylphenyl)-1H-pyrrol-2-yl)(phenyl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With potassium carbonate; In ethanol;Reflux;	General procedure: The synthesis of 2-aminopyrrole analogues was based on a multicomponent reaction by refluxing a solution of three reactants including a methylsulfonamidoacetophenone, an aldehydes and acyanoacetic acid with 0.6 equiv of K2CO3 in ethanol. This reaction results in three substituted 2-aminopyrroles [35]. Compounds1-30 in Tables 1 and 2, and Fig. 3 were synthesized as shown in Scheme 1.

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 139,p. 633 - 643

62
[ 456-14-4 ]
[ 15764-16-6 ]
[ 536-74-3 ]
4-(2,4-dimethylphenyl)-2-(4-fluorophenyl)-6-phenylpyrimidine [ No CAS ]