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[ CAS No. 919301-53-4 ] {[proInfo.proName]}

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Chemical Structure| 919301-53-4
Chemical Structure| 919301-53-4
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Product Details of [ 919301-53-4 ]

CAS No. :919301-53-4 MDL No. :MFCD29477692
Formula : C22H15ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :AJSOWJLBAVMDJX-UHFFFAOYSA-N
M.W : 342.82 Pubchem ID :71425220
Synonyms :

Calculated chemistry of [ 919301-53-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 25
Num. arom. heavy atoms : 24
Fraction Csp3 : 0.0
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 103.35
TPSA : 25.78 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -4.26 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.83
Log Po/w (XLOGP3) : 5.82
Log Po/w (WLOGP) : 6.13
Log Po/w (MLOGP) : 4.62
Log Po/w (SILICOS-IT) : 6.15
Consensus Log Po/w : 5.31

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -6.14
Solubility : 0.000246 mg/ml ; 0.000000717 mol/l
Class : Poorly soluble
Log S (Ali) : -6.13
Solubility : 0.000253 mg/ml ; 0.000000738 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -9.78
Solubility : 0.0000000564 mg/ml ; 0.0000000002 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.53

Safety of [ 919301-53-4 ]

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

Application In Synthesis of [ 919301-53-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 919301-53-4 ]

[ 919301-53-4 ] Synthesis Path-Downstream   1~42

  • 1
  • [ 104-88-1 ]
  • [ CAS Unavailable ]
  • [ 98-86-2 ]
  • [ 919301-53-4 ]
YieldReaction ConditionsOperation in experiment
89% Stage #1: 4-chlorobenzaldehyde; acetophenone at 25℃; for 2.5h; Stage #2: benzonitrile With hydroxylamine at 25℃; for 2.5h; Stage #3: at 150℃; for 0.05h; microwave irradiation; Further stages.;
  • 2
  • [ 956-04-7 ]
  • [ 1670-14-0 ]
  • [ 919301-53-4 ]
YieldReaction ConditionsOperation in experiment
91% With cholin hydroxide In cyclohexanol at 60℃; for 0.416667h; Green chemistry;
  • 3
  • [ 956-04-7 ]
  • [ 618-39-3 ]
  • 4-(4-chlorophenyl)-2,6-diphenylpyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With oxygen; triethylamine In acetonitrile at 80℃; for 5h; General Procedure for the Synthesis of PyrimidineDerivatives General procedure: A round bottom flask was charged with the substitutedchalcone 1 (1.0 mmol), benzamidine 2 (1.0 mmol), triethylamine(2.0 mmol) and acetonitrile (10 mL). The mixturewas heated to 80 °C for 4-14 h, and then cooled to r.t.Evaporation of the solvent gave a crude reaction mixture, towhich water (10 mL) was added and the resulting mixturewas extracted with EtOAc (3 20 mL). The combined organiclayer was washed with 1N HCl (20 mL), brine anddried over anhydrous Na2SO4. The solvent was concentratedunder reduced pressure and residue obtained was purified bysilica gel column chromatography (100-200 mesh) using nhexane:Et2O (95:05) as the eluent to afford the correspondingpyrimidine 3.
  • 4
  • [ 3391-10-4 ]
  • [ 618-39-3 ]
  • [ 100-51-6 ]
  • [ 919301-53-4 ]
YieldReaction ConditionsOperation in experiment
83% With [(4-(4-CF3)-Ph)Tr(NP(iPr)2)(NHP(iPr)2)Ir(cod)]; potassium hydroxide In tert-Amyl alcohol for 24h; Inert atmosphere; Reflux; regioselective reaction;
82% With platinum on activated charcoal; potassium <i>tert</i>-butylate In toluene for 24h; Reflux;
75% With potassium <i>tert</i>-butylate; C22H14N2O In toluene at 70℃; for 8h; Irradiation; Green chemistry;
  • 5
  • [ 919301-53-4 ]
  • [ 1800295-78-6 ]
  • [ 1800295-53-7 ]
YieldReaction ConditionsOperation in experiment
62% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 110℃; for 12h; Inert atmosphere; 17 Synthesis of C-338 Under a nitrogen flow TCA-9 (5.77g, 10.00mmol), 4- (4-chlorophenyl) -2,6-diphenylpyrimidine (4.11g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol) in 100ml toluene was stirred for 12 hours at 110 ° C. After completion of the reaction and extracted with methylene chloride and the filter insert MgSO4. The solvent of the organic layer was filtered to obtain a 338-C (5.47g, 62% yield) of the desired compound by column chromatography.
  • 6
  • [ 919301-53-4 ]
  • [ 1370034-53-9 ]
  • [ 1800295-38-8 ]
YieldReaction ConditionsOperation in experiment
75% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 110℃; for 12h; Inert atmosphere; 2 Synthesis of C-2 Under a nitrogen flow TCA-1(5.93g, 10.00mmol), 4-(4-chlorophenyl)-2,6-diphenylpyrimidine (4.11g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t -Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol) in 100ml toluene was stirred for 12 hours at 110 ° C. After completion of the reaction and extracted with methylene chloride and the filter insert MgSO4. The solvent of the organic layer was filtered to give a 2-C (7.75g, 75% yield) of the desired compound by column chromatography.
  • 7
  • [ 29509-91-9 ]
  • [ 1679-18-1 ]
  • 4-(4-chlorophenyl)-2,6-diphenylpyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 5h;Inert atmosphere; Heating; Under nitrogen atmosphere, <strong>[29509-91-9]4-chloro-2,6-diphenylpyrimidine</strong> (37.3g, 0.14mol) and 4-chlorophenylboronic acid (23.8g, 0.15mol) completely dissolved in 150mL of tetrahydrofuran, was added 2M aqueous potassium carbonate solution (80mL) and tetrakis(triphenylphosphine)palladium (3.2g, 2.7mmol) then heated and stirred for 5 hours. The temperature was lowered to room temperature, the aqueous layer is removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and treated with a column with 1:6 ratio of tetrahydrofuran and hexane to prepare the compound 1-A (34g, yield: 71%).
71% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 5h;Inert atmosphere; Heating; The pyrimidine compound 4-chloro-2,6-diphenyl-pyrido in a nitrogen atmosphere (37.3g, 0.14mol), 4-chloro-phenyl beam to nick the seed (23.8g, 0.15mol) was completely dissolved in tetra hydro furan 150ml 2M was added to aqueous potassium carbonate solution (80ml) and tetrakis- (triphenylphosphine) palladium, insert (3.2g, 2.7mmol) was heated and stirred for 5 hours. Cooled to room temperature to remove the water layer and dried over anhydrous magnesium sulfate and concentrated under reduced pressure and tetrahydrofuran: hexane = 1: 6-F column with the compound 2 (34g, yield: 71%) was prepared as a.
  • 8
  • [ 919301-53-4 ]
  • [ 1689537-46-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tricyclohexylphosphine; potassium acetate; bis(dibenzylideneacetone)-palladium(0) / 1,4-dioxane / 10 h / Inert atmosphere; Reflux 2: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 2 h / Heating
  • 9
  • [ 919301-53-4 ]
  • [ 73183-34-3 ]
  • [ 1536209-84-3 ]
YieldReaction ConditionsOperation in experiment
83% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); potassium acetate In 1,4-dioxane for 24h; Inert atmosphere; Reflux; 7 Preparation of compound 7-2 Compound 7-1 (27.4g, 0.08mol), Boric acid pinacol ester (30.5g, 0.12mol) And potassium acetate (24g, 0.24mol) Add it to a flask containing 1,4-dioxane (300mL), After replacing the nitrogen with stirring at room temperature, Pd2(dba)3 (733 mg, 0.8 mmol) and sphos (1 g, 1.6 mmol) were added. . After the addition is complete, the reaction is stirred and refluxed for 24 hours, and the end of the reaction is monitored by TLC. The precipitated solid was filtered. It was washed with water and dried to obtain compound 7-2 (28.8 g, yield 83%).
81% With potassium acetate; bis(dibenzylideneacetone)-palladium(0); tricyclohexylphosphine In 1,4-dioxane for 10h; Inert atmosphere; Reflux; 1.2 2) Synthesis of compound 1-B Under nitrogen atmosphere, compound 1-A (34.9g, 98.9mmol), bis(pinacolato)diboron (27.6g, 108mmol) and potassium acetate (29.1g, 296mmol) were mixed and added 100mL of dioxane with heating while stirring. Under reflux, bis(dibenzylideneacetone)palladium (1.7g, 2.94mmol) and tricyclohexylphosphine (1.6g, 5.9mmol) were added, heated and stirred for 10 hours. After completion of the reaction, the temperature was lowered to room temperature then filtered. The filtrate was poured into water. It was extracted by chloroform and the organic layer was dried over anhydrous magnesium sulfate. After carrying out distillation under reduced pressure, recrystallization with ethanol to give compound 1-B (35g, yield: 81%).
81% With potassium acetate; bis(dibenzylideneacetone)-palladium(0); tricyclohexylphosphine In 1,4-dioxane for 10h; Inert atmosphere; Reflux; 7.2 Compounds Synthesis of 2-G The compound F-2 (34.9g, 98.9mmol) in a nitrogen atmosphere, bis (pinacolato) Mixing the die boron (27.6g, 108mmol) and potassium acetate (29.1g, 296mmol) and heated with stirring in dioxane was added 100ml It was. In which reflux bis (dibenzylideneacetone naphthyridin-acetone) was added palladium (1.7g, 2.94mmol) and tri-cyclohexyl phosphine (1.6g, 5.9mmol) was heated and stirred, for 10 hours. After the reaction was filtered lowered to room temperature and then terminated. The filtrate was poured into water extracted with chloroform, the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure was recrystallized with ethanol, the compound 2-G (35g, yield: 81%) was prepared.
  • 10
  • [ 919301-53-4 ]
  • [ 1966142-57-3 ]
  • [ 1966142-40-4 ]
YieldReaction ConditionsOperation in experiment
73% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 110℃; for 4h; Inert atmosphere; 8 [Synthesis Example 8] Synthesis of R15 Under a nitrogen flow A4 2.3g (6.4mmol), 4-(4-chlorophenyl)-2,6-diphenylpyrimidine, 2.4g(7.1 mmol), 0.3g (5 mol%) of Pd2 (dba)3, tri-tert -butylphosphine, 0.1g (0.3mmol) and Sodium tert-butoxide, 1.9g (19.3mmol) and 50ml of Toluene was stirred for 4 hours at 110 °C. After the reaction was terminated, the separation of the organic phase with methylene chloride and then the water was removed using MgSO4. Purified by column chromatography to give the title compound, R15, 3.1g (4.7mmol, 73% yield).
  • 11
  • [ 637-87-6 ]
  • [ 1670-14-0 ]
  • [ 98-88-4 ]
  • [ 4301-14-8 ]
  • [ 919301-53-4 ]
YieldReaction ConditionsOperation in experiment
43% Stage #1: 1-Chloro-4-iodobenzene; acetylenemagnesium bromide With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 45℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: benzoyl chloride With copper(l) iodide; triethylamine hydrochloride; triethylamine at 45℃; Schlenk technique; Inert atmosphere; Stage #3: benzamidine monohydrochloride With potassium carbonate In tetrahydrofuran; 2-methoxy-ethanol; water at 90℃; for 16h; Schlenk technique; Inert atmosphere;
YieldReaction ConditionsOperation in experiment
88% With [2,2]bipyridinyl; copper(I) bromide In dimethyl sulfoxide at 90℃; General procedure: Added 25mL round bottom flask 1.0 mmol chalcones and 1.2mmol amidine, followed by addition of 3.0mL of dimethyl sulfoxide, 1.0mmol 2.0mmol cuprous bromide and 2,2'-bipyridyl, at 90°C reaction conditions, monitoring the reaction by TLC. after completion of the reaction, the use of column chromatography, which obtained 2,4,6-substituted pyrimidines, according to this method by selecting a different starting materials the following compounds were synthesized
83% With ammonium formate; toluene-4-sulfonic acid In N,N-dimethyl-formamide at 100℃; for 12h; 10 Embodiment 10-19 General procedure: Stirring of benzaldehyde derivative (II) (20 mmol), benzaldehyde derivative (III) (10 mmol), ammonium formate (30 mmol) and p-toluenesulfonic acid (860 mg, 5 mmol) in DMF (10 mL) at 100 ° C Reaction for 12 hours. After completion of the reaction, the mixture was combined with EtOAc (EtOAc) (EtOAc) The target compound (Ij-s), the reaction formula is shown in Figure 5; the raw material selection and results are shown in Table 1.
With tetrakis(triphenylphosphine) palladium(0); calcium carbonate In tetrahydrofuran for 12h; 6 General procedure: 2-chloro-4,6-diphenyl-1,3,5-triazine (26.7 g, 100 mmol) and 4-chlorophenyl 4-chlorophenyl boronic acid (15.6 g, 100 mmol) was dissolved in tetrahydrofuran (THF)Aqueous solution of calcium carbonate was added, and 0.01 equivalent of Pd (PPh3) 4 catalyst was added thereto, followed by boiling and stirring. After stirring for 12 hours,After cooling to room temperature, the organic layer was separated and recrystallized from chloroform and ethanol to obtain 1-6A white solid (31 g, yield 88%).
58 % With tetrakis(triphenylphosphine) palladium(0); tetrabutyl-ammonium chloride; potassium carbonate In ethanol; water; toluene at 80℃; (iii) Preparation of the Intermediate A-1-5 General procedure: The intermediate A-0-1 (25.8 g, 74.40 mmol), p-chlorophenylboronic acid (11.58 g, 74.60 mmol), tetrakis(triphenylphosphine)palladium (1.70 g, 1.45 mmol), potassium carbonate (22.71 g, 164.35 mmol), and tetrabutylammonium chloride (TBAC) (1.03 g, 3.73 mmol) were respectively added to a three-necked flask; then methylbenzene (160 mL), ethanol (80 mL), and water (40 mL) were added to the flask, and the mixture was heated to reflux and stirred for 12 h at 80° C. After the reaction is completed, CH2Cl2 and water were used for extraction; the separated organic phase was dried over anhydrous MgSO4 and filtered. The filtrate was concentrated in vacuo to obtain a crude product. The crude product was purified by silica gel column chromatography to obtain intermediate A-1-5 (21.5 g, yield 68.7).

  • 13
  • [ 98-85-1 ]
  • [ 618-39-3 ]
  • [ 873-76-7 ]
  • [ 919301-53-4 ]
YieldReaction ConditionsOperation in experiment
84% With platinum on activated charcoal; potassium <i>tert</i>-butylate In toluene for 24h; Reflux;
69% With potassium <i>tert</i>-butylate; C22H14N2O In toluene at 70℃; for 8h; Irradiation; Green chemistry;
65% With [(N,N'-bis(diisopropylphosphino)-2,6-diaminopyridine)Mn(CO)2H]; potassium <i>tert</i>-butylate; potassium hydroxide In toluene at 80℃; for 16h; Inert atmosphere; Green chemistry;
  • 14
  • [ 1670-14-0 ]
  • [ 104-88-1 ]
  • [ 536-74-3 ]
  • [ 919301-53-4 ]
YieldReaction ConditionsOperation in experiment
81% With copper(II) oxide; potassium hydroxide In N,N-dimethyl-formamide at 140℃; for 24h; 2 4-(4-chlorophenyl)-2,6-diphenyl-pyrimidine, comprising the steps of 0.3mmol of benzamidine hydrochloride and 0.36 mmol of p-chlorobenzaldehyde, 0.45 mmol of phenylacetylene were added thereto, and 0.03 mmol of Cu0, 0.9 mmol of K0H and 2-3 ml of DMF were added thereto, and the reaction was stirred at 140 ° C for 24 hours. product; The product was extracted with ethyl acetate and dried to give the crude product which was purified by silica gel column chromatography (solvent volume ratio petroleum ether: ethyl acetate = 50: 1) to give 4- as a white solid 4- (4-chlorophenyl ) -2,6-diphenylpyrimidine. Yield 81%,
57% With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 120℃; for 12h; Inert atmosphere; Green chemistry;
  • 15
  • [ 98-85-1 ]
  • [ 1670-14-0 ]
  • [ 873-76-7 ]
  • [ 919301-53-4 ]
YieldReaction ConditionsOperation in experiment
90% With bis(3,5-di-(tert-butyl)-2-hydroxyazobenzolato)nickel(II); potassium <i>tert</i>-butylate; oxygen In toluene at 80℃; for 8h;
84% With copper diacetate; potassium hydroxide In toluene at 120℃; for 24h; 3A; 3B Synthesis of 4-(4-chlorophenyl)-2,6-diphenylpyrimidine, including the following steps: A, taking 0.3 mmol of benzamidine hydrochloride and 0.39 mmol of p-chlorobenzyl alcohol, 0.40 mmol of 1-phenylethanol,Further, 0.03 mmol of Cu(OAc) 2, 0.9 mmol of KOH and 2.5 mL of toluene were added thereto, and the reaction was stirred at 120 ° C for 24 hours;B, the product was extracted with ethyl acetate, and dried to give a crude product. The crude product was purified by silica gel column chromatography (yield: petroleum ether: ethyl acetate = 50:1) to give a white solid, 4- 4- Chlorophenyl)-2,6-diphenylpyrimidine, 84%, melting point 164 °C.
84% With copper diacetate; potassium hydroxide In toluene at 110℃; for 24h; Green chemistry;
  • 16
  • [ 613-92-3 ]
  • [ 956-02-5 ]
  • 4-(4-chlorophenyl)-2,6-diphenylpyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With 1,10-Phenanthroline; iron(III) chloride hexahydrate; potassium carbonate In toluene at 120℃; for 10h; 2. General procedure for the synthesis of 2,4,6-triphenylpyrimidine 4ab General procedure: The reactions were carried out in a round-bottom sidearm flask (10 mL). 1a (0.2 mmol), 2b (0.4 mmol), FeCl3.6H2O (10 mol%), 1,10-phen (10 mol%), K2CO3 (2 eq) and Toluene (2 mL) were added to the flask with magnetic stirring bar. The resulting mixture was stirred at 120 °C for 10 h. After cooling to room temperature, the mixture was filtered and extracted with ethyl acetate (3×10 mL). Then the filtrate was concentrated under reduced pressure in order to get the crude product, which was further purified by silica gel chromatography (petroleum/ethyl acetate = 50/1 as eluent) to obtain product 4ab.
  • 17
  • [ 618-39-3 ]
  • [ 166823-92-3 ]
  • 4-(4-chlorophenyl)-2,6-diphenylpyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With oxygen In toluene at 110℃; for 18h; Green chemistry; 2.2. General procedure for K-OMS-2-catalyzed pyrimidine synthesis General procedure: All catalytic reactions were performed with oxygen balloons. Cinnamyl alcohol (0.6 mmol), amidine (0.4 mmol), and K-OMS-2 (13 mol%, 40 mg) were placed in a Schlenk flask with an O2 balloon. Air was removed, and PhMe (2 ml) was added into the tube using a syringe. If cinnamyl alcohol was used in the liquid form, then it was added after toluene using a syringe. Then, the reaction mixture was stirred at 110 °C for 18 h under O2 atmosphere. After the reaction, the reaction mixture was cooled and separated by filtration. The filtrate was concentrated using a rotary evaporator, and the crude product was purified by silica gel chromatography to obtain the pure product.
  • 18
  • [ 99-91-2 ]
  • [ 100-52-7 ]
  • [ 919301-53-4 ]
YieldReaction ConditionsOperation in experiment
83% With sodium periodate; ammonium acetate; oxygen; dimethyl sulfoxide In chlorobenzene at 130℃; for 10h;
74 % With boron trifluoride diethyl etherate; 1,1,1,3,3,3-hexamethyl-disilazane In toluene at 150℃; Microwave irradiation;
  • 19
  • 4-(4-chlorophenyl)-2,6-diphenylpyrimidine [ No CAS ]
  • [ 194470-10-5 ]
  • C35H22N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 24h; Inert atmosphere; Reflux; 8-10 <Preparation Example 8> Synthesis of the following compound 8 Under the protection of nitrogen, 9-fluorenone-1-boronic acid (5.0g, 22.32mmol),2-(4-chlorophenyl)-4,6-diphenyl-1,5-pyrimidine (8.63g, 22.32mmol),Tetrakis(triphenylphosphine)palladium (773.39mg, 0.67mmol) and anhydrous potassium carbonate (6.16g, 44.64mmol) were placed in a 250mL round bottom flask,And add 90mL tetrahydrofuran and 22mL distilled water. The above mixture was heated to reflux for 24 hours.After the reaction is over, the temperature is reduced to room temperature, filtered with suction, and washed with a large amount of distilled water,Then, it was purified by recrystallization with dichloromethane/ethanol to obtain Intermediate 8 (8.68 g, yield about 80%), which was dried for later use.Under the protection of nitrogen, put Intermediate 2 (6.68g, 15.38mmol) in a 250mL two-necked flask,Add 77mL of anhydrous tetrahydrofuran to dissolve it, then place it at minus 78 degrees Celsius,Add 2.4M n-butyllithium solution (6.41mL, 15.38mmol) dropwise and stir for 1 hour at minus 78 degrees Celsius.Intermediate 8 (4.97 g, 10.26 mmol) was added, stirred overnight and then quenched by adding 20 mL of distilled water.The tetrahydrofuran was removed from the reaction solution under reduced pressure, and 40 mL of dichloromethane was added to extract 3 times.The dichloromethane was removed under reduced pressure, ethanol was added for recrystallization, and the solid obtained after suction filtration and drying was placed in a 250 mL flask.Add 100 mL of acetic acid and stir for 10 minutes, then add 3 mL of concentrated hydrochloric acid and heat to 110 degrees Celsius to reflux for 3 hours.At the end of the reaction, the temperature dropped to room temperature, the reaction solution was poured into 500 mL ice water, and the product precipitated.After suction filtration, silica gel column chromatography was performed with an eluent of dichloromethane and petroleum ether to obtain compound 8 (7.03 g, 8.52 mmol, yield about 83%).
  • 20
  • [ 919301-53-4 ]
  • [ 2492526-08-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 24 h / Inert atmosphere; Reflux 2.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 2.2: Inert atmosphere 3.1: acetic acid; hydrogenchloride / 3 h / 110 °C
  • 21
  • [ 919301-53-4 ]
  • [ 2492527-35-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 24 h / Inert atmosphere; Reflux 2.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 2.2: Inert atmosphere 3.1: acetic acid; hydrogenchloride / 3 h / 110 °C
  • 22
  • [ 919301-53-4 ]
  • [ 2492530-63-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 24 h / Inert atmosphere; Reflux 2.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 2.2: Inert atmosphere
  • 23
  • [ 919301-53-4 ]
  • [ 2492530-64-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 24 h / Inert atmosphere; Reflux 2.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 2.2: Inert atmosphere
  • 24
  • [ 919301-53-4 ]
  • [ 1024598-06-8 ]
  • [ 1365999-64-9 ]
YieldReaction ConditionsOperation in experiment
70% With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene at 20℃; Reflux; 3-1 Synthesis Example 3-1. Synthesis of Compound 3-1 [0295] [0296] 11-phenyl-11,12-dihydroindolo[2,3-a]carbazole (15 g, 45.1 mmol), 4-(4-chlorophenyl)-2,6-diphenylpyrimidine (15.62 g, 45.57 mmol), and sodium-t-butoxide (6.06 g, 63.1 mol) were mixed with xylene, the resulting mixture was heated and stirred, and then refluxed, and [bis(tri-t-butylphosphine)]palladium (230 mg, 1 mol %) was added thereto. After the temperature was lowered to room temperature and the reaction was terminated, the resulting product was recrystallized by using tetrahydrofuran and ethyl acetate to prepare Compound 3-1 (20.19 g, 70%). [0297] MS[M+H]+=639.77
  • 25
  • [ 919301-53-4 ]
  • [ 2412964-03-3 ]
  • [ 1799293-66-5 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 8h; Heating; 4 Preparation Example 1: Preparation of Compound EC1 General procedure: After completely dissolving Compound EC1-A (10 g, 36.6 mmol) and Compound EC1-B (18.7 g, 36.6 mmol) in tetrahydrofuran (200 mL), potassium carbonate (15.2 g, 109.8 mmol) dissolved in water (60 mL) was added thereto. Tetrakistriphenyl-phosphinopalladium (1.37 g, 0.110 mmol) was introduced thereto, and then the result was stirred for 8 hours while heating. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed to filter white solids. The filtered white solids were washed twice each with tetrahydrofuran and ethyl acetate to prepare Compound EC1 (16.9 g, yield 80%). (0252) MS [M+H]+=578
  • 26
  • [ 1670-14-0 ]
  • [ 102990-14-7 ]
  • [ 919301-53-4 ]
YieldReaction ConditionsOperation in experiment
67% With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 80℃; for 12h; Sealed tube; Inert atmosphere;
  • 27
  • [ 2414517-92-1 ]
  • [ 919301-53-4 ]
YieldReaction ConditionsOperation in experiment
46% With iron(II) chloride In 1,4-dioxane; dimethyl sulfoxide at 130℃; for 10h; Schlenk technique; Inert atmosphere;
  • 28
  • [ 622-98-0 ]
  • [ 1670-14-0 ]
  • [ 18065-04-8 ]
  • [ 919301-53-4 ]
YieldReaction ConditionsOperation in experiment
81% With sodium hydroxide In tert-Amyl alcohol at 110℃; for 20h; 46 Example 1: General procedure: 2-(2-Methoxyphenoxy)-1-benzyl alcohol (0.2 mmol), benzamidine hydrochloride (0.1 mmol), benzyl alcohol (0.2 mmol), NaOH (0.8 mmol) was added to 2 mL tert-pentanol, heated to 110 °C under air conditions, stirred for 20h. After the reaction is completed, cooled to room temperature, added HCl to adjust pH = 1, loaded onto the silica gel chromatography column, elution with eluent, the eluent is petroleum ether and ethyl acetate, the volume ratio is 1:9, the eluent containing the product of interest was collected, 2,4,6-triphenylpyrimidine, yield 95%, to obtain guaiacol, yield 97%;
  • 29
  • [ 100-52-7 ]
  • [ 919301-53-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydroxide / water; ethanol / 0 - 20 °C 2: potassium carbonate; Eosin Y / dimethyl sulfoxide / 4 h / 50 °C / Irradiation
Multi-step reaction with 3 steps 1: sodium hydroxide / water; ethanol / 0 - 20 °C 2: potassium carbonate / dimethyl sulfoxide / 4 h / 50 °C / Darkness 3: Eosin Y / dimethyl sulfoxide / 1 h / 40 °C / Irradiation
  • 30
  • [ CAS Unavailable ]
  • [ 919301-53-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: methanol / 48 h / 20 °C 2: ammonium chloride / methanol / 24 h 3: potassium carbonate; Eosin Y / dimethyl sulfoxide / 4 h / 50 °C / Irradiation
Multi-step reaction with 4 steps 1: methanol / 48 h / 20 °C 2: ammonium chloride / methanol / 24 h 3: potassium carbonate / dimethyl sulfoxide / 4 h / 50 °C / Darkness 4: Eosin Y / dimethyl sulfoxide / 1 h / 40 °C / Irradiation
  • 31
  • [ 7471-86-5 ]
  • [ 919301-53-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ammonium chloride / methanol / 24 h 2: potassium carbonate; Eosin Y / dimethyl sulfoxide / 4 h / 50 °C / Irradiation
Multi-step reaction with 3 steps 1: ammonium chloride / methanol / 24 h 2: potassium carbonate / dimethyl sulfoxide / 4 h / 50 °C / Darkness 3: Eosin Y / dimethyl sulfoxide / 1 h / 40 °C / Irradiation
  • 32
  • [ CAS Unavailable ]
  • [ 919301-53-4 ]
YieldReaction ConditionsOperation in experiment
30.0 mg With Eosin Y In dimethyl sulfoxide at 40℃; Irradiation;
  • 33
  • [ 1670-14-0 ]
  • [ 956-02-5 ]
  • [ 919301-53-4 ]
YieldReaction ConditionsOperation in experiment
79 % With Eosin Y; potassium carbonate In dimethyl sulfoxide at 50℃; Irradiation;
Multi-step reaction with 2 steps 1: potassium carbonate / dimethyl sulfoxide / 4 h / 50 °C / Darkness 2: Eosin Y / dimethyl sulfoxide / 1 h / 40 °C / Irradiation
  • 34
  • [ 99-91-2 ]
  • [ 919301-53-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydroxide / water; ethanol / 0 - 20 °C 2: potassium carbonate; Eosin Y / dimethyl sulfoxide / 4 h / 50 °C / Irradiation
Multi-step reaction with 3 steps 1: sodium hydroxide / water; ethanol / 0 - 20 °C 2: potassium carbonate / dimethyl sulfoxide / 4 h / 50 °C / Darkness 3: Eosin Y / dimethyl sulfoxide / 1 h / 40 °C / Irradiation
  • 35
  • [ 2944087-67-4 ]
  • [ 1527-91-9 ]
  • [ 919301-53-4 ]
YieldReaction ConditionsOperation in experiment
98 % With iron(II) chloride In 1,2-dichloro-ethane at 130℃; Flow reactor; 15 Example 15 1mmol (0.196g) of N-phenylbenzamidine, 0.05mmol (6.25mg) of ferrous chloride were dissolved in 10mL of 1,2-dichloroethane, and the resulting mixed solution was designated as solution A; 2mmol ( 0.598g) of (1E,2E)-1-(4-chlorophenyl)-3-phenylpropyl-2-en-1-one o-acetyl oxime was dissolved in 10mL of 1,2-dichloroethane , the resulting mixed solution is recorded as solution B, and then solution A and solution B are pumped into the microchannel reaction device according to the flow volume ratio of 1:1, and the flow rate is 0.5mL/min respectively, and enter the microchannel reactor after being mixed by the Y-type mixer In the medium (the inner diameter of the polytetrafluoroethylene tube of the microreactor is 0.5 mm, and the volume of the polytetrafluoroethylene tube is 4 mL), react at 130° C. for 8 min.The organic phase was obtained from the discharge of the microreactor, and concentrated in vacuo to obtain a crude product, which was separated by developer column chromatography with a ratio of petroleum ether to ethyl acetate of 30:1 to obtain the target product 11 with a yield of 98%.
  • 36
  • [ 3740-92-9 ]
  • [ 919301-53-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 12 h / 60 °C 2: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 12 h / 60 °C
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 12 h / 60 °C 2: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 12 h / 60 °C
  • 37
  • [ 98-80-6 ]
  • [ 919301-53-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 12 h / 60 °C 2: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 12 h / 60 °C
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 12 h / 60 °C 2: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 12 h / 60 °C
  • 38
  • [ 919301-53-4 ]
  • [ 2923833-55-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 12 h / 100 °C 2: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 12 h / 60 °C
  • 39
  • [ 919301-53-4 ]
  • [ 2930739-45-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 12 h / 100 °C 2: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 12 h / 60 °C
  • 40
  • [ 919301-53-4 ]
  • [ 2930739-26-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 12 h / 100 °C 2: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 12 h / 60 °C
  • 41
  • [ 919301-53-4 ]
  • [ 2930739-28-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 12 h / 100 °C 2: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 12 h / 60 °C
  • 42
  • [ 919301-53-4 ]
  • [ 2930739-39-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 12 h / 100 °C 2: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 12 h / 60 °C
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