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Product Details of [ 7697-46-3 ]

CAS No. :7697-46-3 MDL No. :MFCD00094048
Formula : C11H9NO Boiling Point : -
Linear Structure Formula :- InChI Key :NFGGQMYSOLVBLF-UHFFFAOYSA-N
M.W : 171.20 Pubchem ID :24370
Synonyms :

Safety of [ 7697-46-3 ]

Signal Word:Warning Class:
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:
Hazard Statements:H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 7697-46-3 ]

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

  • Downstream synthetic route of [ 7697-46-3 ]

[ 7697-46-3 ] Synthesis Path-Downstream   1~56

  • 1
  • [ 5145-65-3 ]
  • [ 7697-46-3 ]
YieldReaction ConditionsOperation in experiment
81% With lithium hexamethyldisilazane In tetrahydrofuran; toluene at 100℃; for 3h; Inert atmosphere; 1 Preparation and characterization of compound -1: Under the protection of nitrogen, N-benzoylpyrrole (17.1mg, 0.1mmol) was dissolved in 1mL of toluene, and the tetrahydrofuran solvent of lithium hexamethyldisilazide (1.0mol/L, 0.3 mL, 0.3mmol), reacted under heating at 100°C for 3 hours, then added 3 drops of water to quench the reaction, added a small amount of silica gel powder, filtered, washed with ethyl acetate, evaporated to dryness under reduced pressure, and the mixture was separated by column chromatography (PE: EA=20:110:1) to obtain the target compound II-1, a white solid, with a yield of 81%;.
bei der Destillation durch ein schwach gluehendes Rohr;
  • 2
  • [ 109-97-7 ]
  • [ 1468-28-6 ]
  • [ 7697-46-3 ]
YieldReaction ConditionsOperation in experiment
98% Stage #1: 4-benzoylmorpholine With trichlorophosphate at 20℃; for 5h; Inert atmosphere; Stage #2: pyrrole In dichloromethane at 20℃; for 16h; Inert atmosphere;
90% With trichlorophosphate In 1,2-dichloro-ethane
88% Stage #1: 4-benzoylmorpholine With trichlorophosphate at 20℃; for 5.5h; Inert atmosphere; Stage #2: pyrrole In dichloromethane at 20℃; for 20h; Inert atmosphere; 1 4.3. General procedure (method B) for the 2-aroylation of pyrrole. Preparation of compounds 9a, 9c, and 9d General procedure: The appropriate N-aroylmorpholine (132 mmol) and POCl3 (26.4 mL, 43.5 g, 284 mmol) were mixed under argon atmosphere and stirred at room temperature for 5.5 h. Pyrrole (6.06 mL, 5.86 g, 87.3 mmol) dissolved in dichloromethane (500 mL) was added to the Vilsmeier reagent before being stirred at room temperature for 20 h. Aqueous saturated Na2CO3 solution (667 mL) was then added and the mixture was stirred at room temperature for 15 min and then at reflux for 45 min. The mixture was cooled, the organic layer was separated, washed with water and brine, dried over MgSO4, and concentrated. The crude material was purified by flash chromatography (Merck 107736 Silica gel 60 H, toluene), and recrystallized from the appropriate solvent (given after melting point data in parentheses).
88% Stage #1: 4-benzoylmorpholine With trichlorophosphate at 20℃; for 5h; Inert atmosphere; Stage #2: pyrrole In dichloromethane at 20℃; Inert atmosphere;
80.1% Stage #1: 4-benzoylmorpholine With trichlorophosphate at 20℃; Inert atmosphere; Stage #2: pyrrole In dichloromethane for 24h; Inert atmosphere; 2.9 Compound 7 To 20 mL of POCl3 was added compound 6 (23.8 g, 0.1245 mol) under argon protection, then the reaction mixture was stirred at r.t. overnight. After dropwise added the solution of pyrrole (11.1 g, 11.5 mL, 0.1656 mol) in DCM (30 mL), the reaction was stirred for another 24 h. The reaction was quenched by saturated NaHCO3 in an ice bath. The resulting mixture was stirred at r.t. for 1 h, then heated to reflux with stirring for another 2 h. The organic phase was washed by water (30 mL×3), then dried over Na2SO4 and evaporated in vacuum. The residue was purified by silica gel column (hexane:ethyl actate = 40: 1) to afford 7 (17.06 g, 80.1%). 1H NMR (400MHz, CDCl3), δ 10.93 (s, 1H), 7.94 (d, 2H), 7.65 (t, 1H), 7.56 (t, 2H), 7.28 (s, 1H), 6.39 (d, 1H).
30% Stage #1: 4-benzoylmorpholine With trichlorophosphate at 20℃; Inert atmosphere; Stage #2: pyrrole In dichloromethane at 20℃; for 24h; Inert atmosphere;
With trichlorophosphate 1.) r.t., 5.5 h, 2.) 1,2-dichloroethane, r.t., 20 h; Yield given. Multistep reaction;
With trichlorophosphate In 1,2-dichloro-ethane
Stage #1: pyrrole; 4-benzoylmorpholine With trichlorophosphate Stage #2: With water monomer; anhydrous Sodium acetate
Yield given. Multistep reaction;

  • 3
  • [ 109-97-7 ]
  • [ 201230-82-2 ]
  • [ 73728-29-7 ]
  • [ 3042-22-6 ]
  • [ 5145-65-3 ]
  • [ 7697-46-3 ]
  • [ 27649-43-0 ]
  • [ 7126-41-2 ]
  • 4
  • [ 109-97-7 ]
  • [ 98-88-4 ]
  • [ 7697-46-3 ]
YieldReaction ConditionsOperation in experiment
88% With polystyrene supported aluminium triflate at 20℃; for 2h; Neat (no solvent); regioselective reaction;
85% With zinc(II) oxide In neat (no solvent) at 20℃; for 0.0833333h; Green chemistry; regioselective reaction;
75% With potassium carbonate; zinc In toluene at -50 - 20℃; Inert atmosphere; regioselective reaction; 4 4.1. General procedure for the synthesis of 2-acyl-pyrrole General procedure: To a mixture of pyrrole (1equiv), potassium carbonate (1.5equiv) and zinc powder (2equiv) in toluene (2mL/mmol) at -50°C, acyl chloride (1.5equiv) was added slowly. The mixture was warmed slowly to room temperature. After completion by TLC analysis, the reaction mixture was quenched with saturated sodium bicarbonate solution (3mL/mmol) and extracted with ethyl acetate (2×3mL/mmol). Evaporation of the solvent followed by purification on a short plug of silica gel (Merck, 100-200 mesh, ethyl acetate/hexane, 0.5-9.5) afforded the pure 2-acyl pyrrole derivative
55% With aluminum (III) chloride In dichloromethane
48% Stage #1: pyrrole With ethylmagnesium bromide In diethyl ether for 0.5h; Inert atmosphere; Reflux; Stage #2: benzoyl chloride In diethyl ether at 20℃; Inert atmosphere; 1 4.2. General procedure (method A) for the 2-aroylation of pyrrole. Preparation of compounds 9a-n General procedure: To a freshly prepared solution of ethylmagnesium bromide (90 mmol) in diethyl ether (32 mL) was added dropwise a solution of pyrrole (6.06 mL, 5.86 g, 87.3 mmol) in diethyl ether (40 mL) under reflux. After the addition was complete, the solution was refluxed for a further 30 min. Then the reaction mixture was cooled to room temperature, and the appropriate aroyl chloride (104.9 mmol) dissolved in diethyl ether or tetrahydrofuran (100 mL) was added dropwise over a period of 1 h. The solution was stirred overnight. The reaction mixture was then poured onto a concentrated aqueous ammonium chloride solution (200 mL), extracted with dichloromethane (200 mL), the organic layer was washed with water (3×100 mL), dried over MgSO4, filtered, and evaporated. The crude material was purified by flash chromatography (Merck 107736 Silica gel 60 H, toluene), and recrystallized from the appropriate solvent (given after melting point data in parentheses).
36% With aluminium trichloride Heating;
With ethylmagnesium bromide 1.) ether, reflux, 30 min, 2.) ether, r.t., 23 h; Yield given. Multistep reaction;
With aluminium trichloride
With zinc In diethyl ether at 0℃; for 3h;
With aluminum (III) chloride In dichloromethane
Stage #1: pyrrole With ethylmagnesium bromide In diethyl ether for 0.5h; Heating / reflux; Stage #2: benzoyl chloride In diethyl ether at 20℃; for 25.5h; 1.1 Into a 250 ml roundbottom flask was placed a solution of ethylmagnesium bromide (16.7 g, 125.28 mmol, 1.00 equiv) in ether (40 ml). This was followed by the addition of a solution of lH-pyrrole (8.4 g, 125.30 mmol, 1.00 equiv) in ether (40 ml), which was added dropwise with stirring, while the temperature was maintained at reflux. The resulting solution was allowed to react for 0.5 hours while the temperature was maintained at reflux. It was then cooled to room temperature and a solution of benzoyl chloride (21 g, 150.00 mmol, 1.20 equiv) in ether (40 ml), was added dropwise over 1.5 hours. The resulting solution was stirred for 24 hr, then quenched by adding 100 ml of ammonium chloride. The resulting solution was extracted two times with 100 ml of ether and the organic layers combined. The resulting mixture was washed once with 50 ml of NaCl (aq). The mixture was dried over magnesium sulfate and concentrated by evaporation under vacuum using a rotary evaporator. The residue was purified by eluting through a column with a 1 :20 EtOAc/PE solvent system. This resulted in 8.4 g (crude) of phenyl(lH-pyrrol-2-yl)methanone as a light yellow solid.

Reference: [1]Location in patent: experimental part Boroujeni, Kaveh Parvanak [Bulletin of the Korean Chemical Society, 2010, vol. 31, # 11, p. 3156 - 3158]
[2]Zhang, Shuguang; Feng, Chengliang; Cai, Jin; Chen, Junqing; Hu, Huayou; Ji, Min [Journal of Chemical Research, 2013, vol. 37, # 8, p. 480 - 482]
[3]Faye, Djiby; Mbaye, Mbaye Diagne; Coufourier, Sébastien; Lator, Alexis; Dieng, Samba Yandé; Gaillard, Sylvain; Renaud, Jean-Luc [Comptes Rendus Chimie, 2017, vol. 20, # 5, p. 492 - 499]
[4]Garg; Ganapathi; Rajakannu; Ravikanth [Physical Chemistry Chemical Physics, 2015, vol. 17, # 29, p. 19465 - 19473]
[5]Milen, Mátyás; Ábrányi-Balogh, Péter; Dancsó, András; Simig, Gyula; Volk, Balázs [Tetrahedron, 2014, vol. 70, # 2, p. 465 - 476]
[6]Jeon, Kyu Ok; Jun, Jung Ho; Yu, Ji Sook; Lee, Chang Kiu [Journal of Heterocyclic Chemistry, 2003, vol. 40, # 5, p. 763 - 771]
[7]Wallace, David M.; Leung, Sam H.; Senge, Mathias O.; Smith, Kevin M. [Journal of Organic Chemistry, 1993, vol. 58, # 25, p. 7245 - 7257]
[8]Lee; Lindsey [Tetrahedron, 1994, vol. 50, # 39, p. 11427 - 11440]
[9]Lv, Kai; Wang, Li-Li; Zhou, Xin-Bo; Liu, Ming-Liang; Liu, Hong-Ying; Zheng, Zhi-Bing; Li, Song [Medicinal Chemistry Research, 2013, vol. 22, # 4, p. 1723 - 1729]
[10]Ganapathi, Emandi; Chatterjee, Tamal; Ravikanth, Mangalampalli [European Journal of Organic Chemistry, 2014, vol. 2014, # 30, p. 6701 - 6706]
[11]Current Patent Assignee: KALYPSYS, INC. - WO2008/67222, 2008, A1 Location in patent: Page/Page column 64
  • 6
  • [ 109-97-7 ]
  • [ 611-74-5 ]
  • [ 7697-46-3 ]
YieldReaction ConditionsOperation in experiment
85% Stage #1: N,N-dimethylbenzamide With bis(trichloromethyl) carbonate In tetrachloromethane at 0℃; Stage #2: pyrrole In tetrachloromethane at 40 - 50℃; for 1h; Stage #3: With sodium hydroxide In tetrachloromethane
40% Stage #1: pyrrole; N,N-dimethylbenzamide With trichlorophosphate In dichloromethane at 60℃; for 18h; Stage #2: With potassium carbonate In dichloromethane; water at 20℃;
Yield given. Multistep reaction;
  • 7
  • [ 7697-46-3 ]
  • [ 6279-86-3 ]
  • [ 136116-84-2 ]
YieldReaction ConditionsOperation in experiment
86% With anhydrous Sodium acetate; manganese(III) triacetate In glacial acetic acid at 60 - 65℃; for 24h;
With anhydrous Sodium acetate; manganese(III) triacetate dihydrate; acetic anhydride In toluene Heating; 1-4 200g (1.17mol, 1.0equiv.) of 2-benzoylpyrrole (SM),Triethyl methane tricarboxylate 406.9g (1.75mol, 1.5equiv.),Manganese acetate dihydrate (trivalent) 469.8g (1.75mol, 1.5equiv.),Sodium acetate 191.7g (2.34mol, 2.0equiv.), acetic anhydride 894.5g (8.76mol, 7.5equiv.) were added to 2000mL of toluene, After heating to complete the reaction,Add about 1000 mL of sodium bisulfite aqueous solution (add 54.7 g of sodium bisulfite (0.53 mol, 0.45 equiv.) to 1000 mL of water for dissolving configuration), and separate the liquids to obtain the organic phase containing the M-1 intermediate, which is recorded as M- 1 solution, proceed directly to the next step;
  • 8
  • [ 7697-46-3 ]
  • [ 76513-69-4 ]
  • [ 87954-23-2 ]
YieldReaction ConditionsOperation in experiment
94% With sodium hydride In tetrahydrofuran 1. 0 deg C 2. 1h, room temperature;
  • 9
  • [ 7697-46-3 ]
  • [ 685-87-0 ]
  • [ 144710-35-0 ]
YieldReaction ConditionsOperation in experiment
86% With triethyl borane; oxygen In hexane; benzene for 3h; Ambient temperature;
284 mg (86%) With triethyl borane In hexane; benzene 4 Compound of Formula III where X is Hydrogen, Diethyl (5-Bonzoylpyrrol-2-yl)metthanedicarboxylate Compound of Formula III where X is Hydrogen, Diethyl (5-Bonzoylpyrrol-2-yl)metthanedicarboxylate To a solution of 2-benzoylpyrrole (171mg, 1 mmol) and diethyl bromomalonate (1185 mg, 5 mmol) in benzene (20 mL) was added triethylborane (1.0 M in hexane, 5 mL, 5 mmol). The reaction mixture was stirred for 1 hour in an open vessel. Additional triethylborane (1 mL, 1 mmol) was added and the reaction was stirred for an additional hour. The mixture was poured into water and extracted with diethyl ether. The ethereal extract was washed with saturated aqueous sodium chloride, dried (Na2 SO4), and concentrated. The residue was purified by column chromatography on silica eluding with hexane/ethyl acetate (87:13) to provide 284 mg (86%) of diethyl (5-benzoylpyrrol-2-yl)methane-dicarboxylate.
  • 10
  • [ 7697-46-3 ]
  • [ 107-06-2 ]
  • [ 87549-01-7 ]
YieldReaction ConditionsOperation in experiment
97% With potassium carbonate at 30℃; for 2h; Molecular sieve; 1-14 Example 5: Dissolve 1H-pyrrol-2-yl-phenyl ketone (50g, 0.29mol) in 300ml of 1,2-dichloroethane, add potassium carbonate (40.4g, 0.29mol), add 100g of NaY molecular sieve, and mix Stir at 30°C and monitor the reaction with TLC. After 2 hours, the spots of the raw materials disappeared. Potassium carbonate and NaY molecular sieve were filtered out. The filtrate was concentrated to dryness under reduced pressure. 100ml ethyl acetate and 100ml n-heptane were added, heated to clear, and cooled. Crystallize below 25, filter,After drying, the compound of Formula I is obtained,It is an off-white solid, a total of 66.2g, with a yield of 97%.
89% With sodium hydroxide; tetra-(n-butyl)ammonium iodide for 1h; Heating;
75%
  • 11
  • [ 7697-46-3 ]
  • [ 609-08-5 ]
  • Diethyl α-methyl-5-benzoyl-2-pyrrolemalonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With sodium acetate; manganese triacetate In acetic acid at 70℃; for 6h;
  • 12
  • [ 7697-46-3 ]
  • [ 33234-48-9 ]
YieldReaction ConditionsOperation in experiment
99% With sodium tetrahydroborate In isopropyl alcohol for 20h; Heating;
91% With hydrazine hydrate In various solvent(s) further reducing agents: lithium aluminium hydride, NaBH4 in aqueous ethanol;
72% With lithium aluminium tetrahydride In tetrahydrofuran for 48h; Heating;
With sodium tetrahydroborate

  • 13
  • [ 7697-46-3 ]
  • [ 50372-61-7 ]
YieldReaction ConditionsOperation in experiment
85% With copper(ll) bromide In acetonitrile for 48h; Ambient temperature;
77% With bromine In dichloromethane 0 deg C to RT, 2.5 h;
76.5% With bromine In dichloromethane 1.A A. A. Preparation of 2,3-dibromo-5-benzoylpyrrole (Step 1) Bromine (15.16 g, 94.7 mmoles) in dichloromethane (250 ml) was added dropwise at 0° over a one hour and 10 minute period, with constant stirring, to a solution of 2-benzoylpyrrole [8.12 g, 4.75 mmoles; prepared according to White, J. Org. Chem. 42 4248, (1977)] in anhydrous dichloromethane (250 ml). The reaction was allowed to rise to room temperature and stirring was continued for 2.5 h. The solvent was evaporated to dryness and the crystalline residue was recrystallized from dichloromethane hexane. A total of 3 crops of the product (11.95 g, 76.5%) was obtained. Further product remained in the mother liquors.
  • 14
  • [ 75400-59-8 ]
  • [ 7697-46-3 ]
YieldReaction ConditionsOperation in experiment
95% With sodium methylate In tetrahydrofuran; methanol for 0.333333h; Ambient temperature;
  • 15
  • [ 86688-89-3 ]
  • [ 7697-46-3 ]
YieldReaction ConditionsOperation in experiment
95% With sodium hydroxide In methanol for 3.5h; Heating;
  • 16
  • [ 7697-46-3 ]
  • [ 5617-70-9 ]
  • 8,8-dimethyl-11-phenyl-4,5-dihydro-11<i>H</i>-7,9,10-trioxa-3a-aza-benzo[<i>a</i>]cyclopenta[<i>e</i>]cycloocten-6-one [ No CAS ]
  • 5-[2-(2-benzoyl-pyrrol-1-yl)-ethyl]-2,2-dimethyl-[1,3]dioxane-4,6-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 17.5% 2: 1.4 g With sodium hydride In N,N-dimethyl-formamide at 25 - 80℃; for 19h;
  • 18
  • [ 7697-46-3 ]
  • [ 351491-23-1 ]
  • 2-(5-benzoylpyrrol-2-yl)propionic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With dilauryl peroxide In 1,2-dichloro-ethane for 12h; Heating;
  • 19
  • [ 109-97-7 ]
  • [ 65-85-0 ]
  • [ 7697-46-3 ]
YieldReaction ConditionsOperation in experiment
98% With aluminium dodecatungsten phosphate; trifluoroacetic anhydride In hexane at -23℃; for 0.4h;
88% With silica gel supported aluminium trichloride at 60℃; for 2.3h; regioselective reaction;
87% With cross-linked polystyrene-supported aluminum triflate at 60℃; for 3.4h; Neat (no solvent); regioselective reaction;
  • 20
  • [ 7697-46-3 ]
  • [ 66909-39-5 ]
  • 3-(5-benzoyl-1<i>H</i>-pyrrol-2-yl)-dihydro-furan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With triethyl borane; iron(II) sulfate In tetrahydrofuran; ethanol; dichloromethane at 20℃;
  • 21
  • [ 7697-46-3 ]
  • [ 73232-07-2 ]
  • 2-(5-benzoyl-1<i>H</i>-pyrrol-2-yl)-propionic acid ethyl ester [ No CAS ]
  • 23
  • [ 7697-46-3 ]
  • [ 92012-34-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 72 percent / lithium aluminum hydride / tetrahydrofuran / 48 h / Heating 2: toluene / 6 h / Heating 3: 1 h / Ambient temperature
  • 24
  • [ 7697-46-3 ]
  • [ 74103-06-3 ]
  • 25
  • [ 7697-46-3 ]
  • 1-sodio-2-benzoylpyrrole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With nitrogen In tetrahydrofuran Route 1 EXAMPLES Route 1 Preparation of 4-(2-Benzoylpyrrol-1-yl)butyric acid methyl ester (III), (Step 1, Scheme 1). Compounds of the type having Formula II can be prepared according to known procedures (J. Org. Chem. 1977, 42, 4248.) and used in Step 1. A solution of 2-benzoylpyrrole (II, 20.0 g, 117 mmoles) in 50 mL of anhydrous tetrahydrofuran was added dropwise to a nitrogen blanketed stirred suspension of sodium hydride (129 mmoles) in 300 mL of anhydrous tetrahydrofuran over the course of 30 minutes. The reaction mixture was stirred under a nitrogen atmosphere for 1 hour after which gas evolution had ceased. The tetrahydrofuran was then evaporated under reduced pressure to leave the 1-sodio-2-benzoylpyrrole as a yellow solid gamma-Butyrolactone (11.0 g, 128 mmoles) was added to the solid and this mixture was protected from moisture with a calcium sulfate drying tube and heated to 135° C. for 5 hours.
  • 26
  • [ 7697-46-3 ]
  • [ 96-32-2 ]
  • [ 106858-73-5 ]
YieldReaction ConditionsOperation in experiment
89% With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide 2 EXAMPLE 2 EXAMPLE 2 This Example illustrates the preparation of (Z)-methyl 3-methoxy-2-[2-benzoylpyrrol-1-yl]acrylate (Compound No. 2 of Table I). Potassium tert-butoxide (7.22, 0.064 mol) was dissolved in DMF (40 ml) and 2-benzoylpyrrole (10 g, 0.058 mol) in DMF (10 ml) was added dropwise with stirring at room temperature. This was left for 16 hours then cooled to 0° C. when methyl bromoacetate (5.4 ml, 0.058 mol) in DMF (5 ml) was added dropwise. The reaction mixture was stirred for 16 hours then poured into water (150 ml) and extracted with diethyl ether (2*100 ml). The extracts were washed with brine (2*75 ml) dried and evaporated to give methyl (2-benzoylpyrrol-1-yl)acetate (12.6 g, 89%) as a brown oil which crystallized on standing.
  • 27
  • [ 7697-46-3 ]
  • [ 87549-01-7 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; tetrabutylammomium bromide In 1,2-dichloro-ethane 1.A 1A. 1A. A Compound of Formula III where X is Chloro, 1-(2-Chlorethyl)-2-benzoylpyrrole To a solution of 2-benzoylpyrrole (9.40 g, 55 mmol) and tetrabutylammonium bromide (17.7 g, 55 mmol) in 1,2-dichloroethane (200 mL) was added cold aqueous sodium hydroxide (0° C, 50 mL, 50%). The reaction mixture was stirred at room temperature for 30 minutes. The organic layer was separated and the aqueous layer was washed with methylene chloride (3*200 mL). The organic layers were combined and concentrated under reduced pressure. The crude product, 1-(2-chloroethyl)-2-benzoylpyrrole, was purified by column chromatography on silica gel eluding with diethyl ether. Yield 11.4 g (89%), mp 54°-55° C.
  • 28
  • [ 7697-46-3 ]
  • [ 865-47-4 ]
  • [ 96-32-2 ]
  • [ 106858-73-5 ]
YieldReaction ConditionsOperation in experiment
89% In N,N-dimethyl-formamide 2 EXAMPLE 2 EXAMPLE 2 This Example illustrates the preparation of (Z)-methyl 3-methoxy-2-[2-benzoylpyrrol-1-yl]acrylate (Compound No. 2 of Table I). Potassium tert -butoxide (7.22, 0.064 mol) was dissolved in DMF (40 ml) and 2-benzoylpyrrole (10g, 0.058mol) in DMF (10ml) was added dropwise with stirring at room temperature. This was left for 16 hours then cooled to 0°C when methyl bromoacetate (5.4ml, 0.058mol) in DMF (5ml) was added dropwise. The reaction mixture was stirred for 16 hours then poured into water (150ml) and extracted with diethyl ether (2 x 100ml). The extracts were washed with brine (2 x 75ml) dried and evaporated to give methyl (2-benzoylpyrrol-1-yl)acetate (12.6g, 89%) as a brown oil which crystallized on standing.
  • 29
  • [ 7697-46-3 ]
  • [ 116861-31-5 ]
  • [ 1030615-39-4 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; Into a 100 ml roundbottom flask was placed a solution of phenyl(lH-pyrrol-2-yl)methanone (3.42 g, 20.00 mmol, 1.00 equiv) in DMF (40 ml). To this was added tert-butyl 3- chloropropylcarbamate (4.65 g, 24.01 mmol, 1.20 equiv) followed by potassium carbonate (22 g, 159.42 mmol, 8.00 equiv). The reaction was then heated to 90 0C and stirred overnight. It was then cooled to room temperature and diluted with 200 ml of water. The resulting solution was extracted three times with 100 ml of ethyl acetate and the organic layers combined. The resulting mixture was washed two times with 50 ml of NaCl (aq). The mixture was dried over magnesium sulfate and concentrated by evaporation under vacuum using a rotary evaporator. The crude tert-butyl 3-(2- benzoyl-lH-pyrrol-l-yl)propylcarbamate was taken immediately to the next step.
  • 30
  • [ 7697-46-3 ]
  • [ 6295-06-3 ]
  • (2S)-2-[5-(phenylcarbonyl)-1H-pyrrol-3-yl]-2-hydroxyacetic acid n-butyl ester [ No CAS ]
  • [ 1338919-47-3 ]
YieldReaction ConditionsOperation in experiment
70% With titanium(IV) isopropylate; (R)-6,6'-dibromo-1,1'-binaphth-2-ol In toluene at 0℃; for 10h; optical yield given as %ee; enantioselective reaction;
  • 31
  • phenyl(1-tosyl-2,5-dihydro-1H-pyrrol-2-yl)methanone [ No CAS ]
  • [ 7697-46-3 ]
YieldReaction ConditionsOperation in experiment
95% With potassium carbonate In methanol at 20℃; for 0.25h;
83% With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,2-dichloro-ethane at 120℃; for 0.0833333h; Microwave irradiation;
  • 32
  • [ 7697-46-3 ]
  • [ 105-36-2 ]
  • [ 13169-84-1 ]
YieldReaction ConditionsOperation in experiment
92% With caesium carbonate In acetonitrile at 20℃; 1 4.4. General procedure for the N-alkylation of 2-aroylpyrroles. Preparation of compounds 10a-p General procedure: The appropriate 2-aroylpyrrole derivative (9, 25.0 mmol) was dissolved in acetonitrile (375 mL). If the mixture did not become a solution (in the cases of 9j, 9k, 9n) 150 mL of CH2Cl2 was added. To this solution were added cesium carbonate (9.77 g, 30.0 mmol) and ethyl α-bromoalkanoate (ethyl bromoacetate, ethyl 2-bromopropionate or ethyl-2-bromobutyrate, 27.5 mmol). The reaction mixture was stirred overnight at room temperature. The mixture was then filtered, evaporated, the residue was then dissolved in dichloromethane, extracted with water twice, dried over MgSO4, filtered and evaporated. The crude material was recrystallized or distilled.
  • 33
  • [ 109-97-7 ]
  • [ 100-52-7 ]
  • [ 7697-46-3 ]
YieldReaction ConditionsOperation in experiment
81.5% Stage #1: pyrrole With n-butyllithium In diethyl ether; hexane at 0 - 20℃; for 2h; Inert atmosphere; Schlenk technique; Stage #2: benzaldehyde With 2,6-dimethylaniline In diethyl ether; hexane at 30℃; for 5.5h; Inert atmosphere; Schlenk technique; General procedure for synthesisof 2-benzoylpyrrole derivatives General procedure: In a typical experiment, to a solution of pyrrole (0.21mL, 3.0 mmol) in dry diethyl ether(20 mL), n-butyllithium (2.5 Min hexane, 1.2 mL, 3.0 mmol) was added at 0°C, the reaction was then allowed to the room temperature and stirred for 2 hour under nitrogen atmosphere. To this suspension, 2, 6-dimethylaniline (0.18 mL,1.5 mmol) was added dropwise and stirred for 30 min. followed by the addition of benzaldehyde (0.61 mL, 6 mmol). Stirring was continued for 5 h at 30°C and the progress of the reaction was monitored by TCL. Reaction mixture was then cooled to room temperature, quenched with saturated aqueous ammonium chloride solution, filtered over Celite and extracted into ethyl acetate. The organic layer was then washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to get the crude mixture. The product was isolated fromthe crude mixture by column chromatography on silica gel using ethyl acetate-hexanemixture (1:7) as an eluent and characterized by spectral methods.
  • 34
  • [ 7697-46-3 ]
  • 2-azido-N-benzyl-N-methylacrylamide [ No CAS ]
  • N-benzyl-N-methyl-1-phenylpyrrolo[1,2-a]pyrazine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; 4.1.6. Synthesis of 1-arylpyrrolo[1,2-a]pyrazine-3-carboxamides1 from arylpyrroleketones 2 and 2-azidoacrylamides 3 General procedure: Solution of 2 mmol of 2-azidoacrylamide 3, 2.2 mmol (0.72 g) ofCs2CO3 and 2 mmol of arylpyrroleketone 2 in 6 ml of dry DMF wasstirred for 24 h at room temperature. The mixture was diluted with30 ml of water and extracted with 4*20 ml of EtOAc. The combinedextracts were washed with 20 ml of water and filtered over paperfilter and evaporated to dryness. The residue was chromatographedon silica gel using a mixture of ethyl acetate and hexane(1:3) as eluent. Appropriate fractions were evaporated todryness and the residue was recrystallized from ethanol to givethe desired product.
  • 35
  • [ 7697-46-3 ]
  • 2-azido-N-butyl-N-methylacrylamide [ No CAS ]
  • N-butyl-N-methyl-1-phenylpyrrolo[1,2-a]pyrazine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; 4.1.6. Synthesis of 1-arylpyrrolo[1,2-a]pyrazine-3-carboxamides1 from arylpyrroleketones 2 and 2-azidoacrylamides 3 General procedure: Solution of 2 mmol of 2-azidoacrylamide 3, 2.2 mmol (0.72 g) ofCs2CO3 and 2 mmol of arylpyrroleketone 2 in 6 ml of dry DMF wasstirred for 24 h at room temperature. The mixture was diluted with30 ml of water and extracted with 4*20 ml of EtOAc. The combinedextracts were washed with 20 ml of water and filtered over paperfilter and evaporated to dryness. The residue was chromatographedon silica gel using a mixture of ethyl acetate and hexane(1:3) as eluent. Appropriate fractions were evaporated todryness and the residue was recrystallized from ethanol to givethe desired product.
  • 36
  • [ 7697-46-3 ]
  • 2-azido-N-(sec-butyl)-N-methylacrylamide [ No CAS ]
  • N-(sec-butyl)-N-methyl-1-phenylpyrrolo[1,2-a]pyrazine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; 4.1.6. Synthesis of 1-arylpyrrolo[1,2-a]pyrazine-3-carboxamides1 from arylpyrroleketones 2 and 2-azidoacrylamides 3 General procedure: Solution of 2 mmol of 2-azidoacrylamide 3, 2.2 mmol (0.72 g) ofCs2CO3 and 2 mmol of arylpyrroleketone 2 in 6 ml of dry DMF wasstirred for 24 h at room temperature. The mixture was diluted with30 ml of water and extracted with 4*20 ml of EtOAc. The combinedextracts were washed with 20 ml of water and filtered over paperfilter and evaporated to dryness. The residue was chromatographedon silica gel using a mixture of ethyl acetate and hexane(1:3) as eluent. Appropriate fractions were evaporated todryness and the residue was recrystallized from ethanol to givethe desired product.
  • 37
  • [ 7697-46-3 ]
  • [ 81852-50-8 ]
  • C16H14N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; 4.1.8. Synthesis of 1-arylpyrrolo[1,2-a]pyrazine-3-carboxylicacids (16) from arylpyrroleketones 2 and ethyl 2-azidoacrylate14 General procedure: Solution of 44 mmol (5.6 g) of methyl 2-azidoacrylate 14,53 mmol (13.3 g) of Cs2CO3 and 34 mmol of arylpyrroleketone 2in 80 ml of dry DMF was stirred for 24 h at room temperature.The mixture was evaporated, diluted with 200 ml of water and50 ml of methanol. 68 mmol (2.7 g) of NaOH was added to thesolution and the mixture was refluxed until complete ester 15saponification that was monitored by TLC. The mixture was cooled,diluted with 100 ml of water and acidified with 36% HCl topH5.The mixture was extracted with 4*40 ml of ethyl acetate.All organic fractions were combined, filtered over paper filter andevaporated to dryness to give the desired product.
  • 38
  • 2-(N-methylbenzenecarboximidoyl)pyrrole hydrogen tetrafluoroborate [ No CAS ]
  • [ 7697-46-3 ]
YieldReaction ConditionsOperation in experiment
58% With water; sodium acetate for 0.166667h; Reflux; 7 12.7. 2-(N-Methylbenzenecarboximidoyl)pyrrole hydrogen tetrafluoroborate (47), 2-(N-methylbenzenecarboximidoyl)pyrrole (52) and 2-benzoylpyrrole (57) Pyrrole (1.90 g, 28 mmol) in dichloromethane (5 mL) was added slowly to a stirred suspension of N-methylbenzonitrilium tetrafluoroborate (5.80 g, 28.3 mmol) in dichloromethane (25 mL) at -50 °C, keeping the temperature below -45 °C during the addition. The reaction mixture was then kept at -22 °C for 24 h to give, as a solid after filtration, 2-(N-methylbenzenecarboximidoyl)pyrrole hydrogen tetrafluoroborate as a mixture of diastereoisomers (47) (6.00 g, 78%) mp 85-89 °C, decomp. (from ethanol): λmax 228 (log10ε 4.33), 287 (4.43) 322 (4.15) nm, νmax 3300, 1605, 1130-980 cm-1, δH (90 MHz, CD3CN) 3.25 (d, 3H J=7 Hz, singlet after D2O exchange), 3.66 (d, 3H J=7 Hz, singlet after D2O exchange), 6.75-6.88 (m, 2H), 7.5-7.95 (m, 6H), 9.45 (br s, 1H), 10.50 (br s, 1H) ppm, δC (20 MHz, CD3CN) (major signals) 35.3, 36.4, 115.6, 115.8, 167.0, 167.8 ppm. The filtrate was added to ice/water (50 mL) and the aqueous layer taken to pH 10 with aqueous sodium hydroxide solution (2 M), extracted with dichloromethane (3 times 30 mL), dried (MgSO4), and evaporated to give 2-(N-methylbenzenecarboximidoyl)pyrrole (52) (4.15 mg 8%), mp 119-120 °C (from CHCl3/light petroleum bp 40-60 °C): λmax 230 (log10ε 4.33) 287 (4.58) nm, νmax 1605 cm-1, δH (90 MHz, CDCl3) 3.24 (s, 3H), 5.98-6.07 (m, 1H), 6.17-6.27 (m, 1H), 6.91-7.00 (m, 1H), 7.24-7.54 (m, 5H), 10.05 (br s, 1H) ppm, δC (20 MHz, CDCl3) 39.8, 109.2, 114.6, 121.9, 128.0, 128.3, 128.5, 133.2, 136.0, 162.8 ppm. HRMS found 184.1004 C12H12N2 requires 184.1000. The imine salts (47) (1.68 g, 6.2 mmol) and sodium acetate (5.00 g, 61 mmol) in water (30 mL) were heated under reflux for 10 min and gave 2-benzoylpyrrole (57), after recrystallization from light petroleum (40-60 °C), 202 mg, 58%, mp 78-79 °C (lit. 63mp 77.5-78 °C): λmax 243 (log10ε 4.34) and 305 (4.66) nm, νmax 3280, 1620 cm-1, δH (90 MHz, CDCl3) 6.30-6.40 (m, 1H), 6.88-6.99 (m, 1H), 7.16-7.28 (m, 1H), 7.42-7.60 (m, 3H), 7.87-8.02 (m, 2H), 8.48 (br s, 1) ppm, δC (20 MHz, CDCl3) 111.0, 120.3, 126.3, 128.4, 129.1, 130.4, 131.9, 138.7, 185.3 ppm. HRMS found 171.0685 C11H9NO requires 171.0684.
  • 39
  • [ 109-97-7 ]
  • [ 98-88-4 ]
  • [ 7697-46-3 ]
  • [ 7126-41-2 ]
  • 40
  • [ 7697-46-3 ]
  • [ 70-11-1 ]
  • 1-phenyl-2-[2-(phenylcarbonyl)-1H-pyrrol-1-yl]ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With caesium carbonate In dichloromethane; acetonitrile at 20℃; for 24h; General procedure for the N-alkylation of 2-aroylpyrroles. Preparation of compounds 13a-13g General procedure: The appropriate 2-aroylpyrrole derivative (11) (2.0 mmol)was dissolved in a mixture of 25 cm3 MeCN and 50 cm3CH2Cl2. To this solution were added 0.847 g Cs2CO3 (2.6 mmol) and 2-bromo-1-phenylethanone or 2-bromo-1-(4-methylphenyl)ethanone (2.4 mmol). The reaction mixture was stirred overnight at room temperature. Later, the inorganic salts were filtered off, and the filtrate was concentrated. The residue was then dissolved in 30 cm3 CH2Cl2, extracted with H2O (29x30 cm3), dried over Na2SO4, filtered, and evaporated. The crude material was purified by flash column chromatography
  • 41
  • [ 7697-46-3 ]
  • [ 619-41-0 ]
  • 1-(4-methylphenyl)-2-[2-(phenylcarbonyl)-1H-pyrrol-1-yl]ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With caesium carbonate In dichloromethane; acetonitrile at 20℃; for 24h; General procedure for the N-alkylation of 2-aroylpyrroles. Preparation of compounds 13a-13g General procedure: The appropriate 2-aroylpyrrole derivative (11) (2.0 mmol)was dissolved in a mixture of 25 cm3 MeCN and 50 cm3CH2Cl2. To this solution were added 0.847 g Cs2CO3 (2.6 mmol) and 2-bromo-1-phenylethanone or 2-bromo-1-(4-methylphenyl)ethanone (2.4 mmol). The reaction mixture was stirred overnight at room temperature. Later, the inorganic salts were filtered off, and the filtrate was concentrated. The residue was then dissolved in 30 cm3 CH2Cl2, extracted with H2O (29x30 cm3), dried over Na2SO4, filtered, and evaporated. The crude material was purified by flash column chromatography
  • 42
  • [ 7697-46-3 ]
  • [ 76-02-8 ]
  • 1-(5-benzoyl-1H-pyrrol-3-yl)-2,2,2-trichloroethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 0.166667h; Inert atmosphere;
84% With aluminum (III) chloride at 0℃; for 20h; Inert atmosphere; Reflux;
  • 43
  • [ 7697-46-3 ]
  • [ 79-03-8 ]
  • 1-(4-benzoyl-1H-pyrrol-2-yl)propan-1-one [ No CAS ]
  • 1-(5-benzoyl-1H-pyrrol-2-yl)propan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 19% 2: 31% With zinc In 1,2-dichloro-ethane at 20℃; Inert atmosphere; regioselective reaction; 21 General procedure for the synthesis of 2,4- and 2,5-diacyl-pyrrole General procedure: General procedure for the synthesis of 2,4- and 2,5-diacyl-pyrrole To a mixture of 2-acylpyrrole 1 (1 equiv) and zinc powder (2 equiv, 59 mg, 0.917 mmol) in dichloroethane (2 mL/mmol) acyl chloride (1.5 equiv) was added. The mixture was stirred at room temperature and, after completion by TLC analysis (16-24 h), the reaction mixture was quenched with saturated sodium bicarbonate solution (15 mL/mmol) and extracted with ethyl acetate (3 * 15 mL/mmol). Evaporation of the solvent followed by purification on silica gel (Merck, 100-200 mesh, ethyl acetate/hexane) afforded the pure 2,4-diacylpyrrole (2) and 2,5-diacylpyrrole (3).
  • 44
  • [ 7697-46-3 ]
  • [ 56-37-1 ]
  • (1-benzyl-1H-pyrrol-2-yl)(phenyl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With sodium hydroxide; In water; toluene; for 2.0h;Reflux; Using the standard procedure, to xylene (10.0mL), 0.5003 g of TEBAC (1.1 Eq) and 0.2996 g of methanone (a) (1.0 Eq) were added, followed by a solution of NaOH 50% (5.0 mL).The mixture was stirred at reflux temperature for 2 h. After cooling to r.t., TLC revealed the disappearance of the startingmaterial. The reaction mix was treated with AcOEt (4 ×20 mL), and the organic phase separated and removed underreduced pressure. The compound was isolated as an offyellowsolid: 1H NMR: (300MHz, CDCl3) delta = 7.81-7.68 (m,2H), 7.53-7.34 (m, 3H), 7.34-7.10 (m, 5H), 7.00 (t, = 2.1Hz,1H), 6.76 (dd, = 4.1, 1.7Hz, 1H), 6.19 (dd, = 4.1, 2.6Hz,1H), 5.65 (s, 2H). 13C NMR: (126MHz, CDCl3) delta= 186.20,171.26, 139.83, 138.28, 131.46, 130.04, 129.24, 128.62, 128.42,127.34, 127.16, 123.70, 108.73, 69.67, 60.44, 52.37.MS [EI+] m/z (%): 306 (M+), 289 (28), 259 (14), 229 (4), 156 (22), 91 (100),65 (17).
  • 45
  • [ 7697-46-3 ]
  • [ 1119-97-7 ]
  • [ 37496-06-3 ]
YieldReaction ConditionsOperation in experiment
76% With sodium hydroxide In water; toluene for 5h; Reflux; chemoselective reaction; 4.2. General Procedure for the Synthesis of 1b-7b and 11b. General procedure: A 100mL round-bottom flask was equipped with a magnetic stir bar and a reflux condenser. To xylene (10.0mL), tetradecyltrimethylammonium bromide (1.1mmol) and a heterocyclic compound (1.0mmol) were added, followed bya solution of NaOH 50% (5.0 mL). The mixture was stirred at reflux temperature for 2-18 h. After completion of thereaction, the mixture was air-jet cooled to 25 °C and TLC indicated the disappearance of the starting material. The reaction mix was treated with AcOEt (4 × 20 mL), and the organic phase separated and removed under reduced pressure. The residue was purified to analytical purity by column chromatography.
  • 46
  • [ 7697-46-3 ]
  • [ 2400-36-4 ]
  • C21H18N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trichlorophosphate In 1,2-dichloro-ethane at 20 - 80℃; for 4h; 3.2. Synthesis of BODIPY 1 To a solution of compound 2a (58.3 mg, 0.341 mmol) in 5mLCH2ClCH2Cl was added POCl3 (0.127 mL, 1.365 mmol), and the reactionmixturewas stirred at room temperature for 1.5 h. A solutionof compound 1 (60.0 mg, 0.373 mmol) in 1, 2-dichoroethane (5 mL)was then added, and the resulting mixture was refluxed for 2.5 h at80 C. The reaction mixture was cooled to room temperature andslowly poured into saturated aqueous NaHCO3 under ice-coldconditions. After being warmed to room temperature, the reactionmixture was extracted with CH2Cl2 and washed with water.The organic layers were dried over anhydrous Na2SO4, then evaporatedin vacuumThe residue was dissolved in CH2ClCH2Cl beforeEt3N (0.379 mL, 2.726 mmol) was added and the mixture wasstirred in ice bath for 5 min. Then BF3-Et2O (0.432 mL, 3.407 mmol)was added. After being warmed to room temperature, the reactionmixture was further stirred for 30 min, extracted with CH2Cl2 andwashed with water. The organic layers were dried over anhydrousNa2SO4, then evaporated in vacuum. The crude product was furtherpurified using column chromatography (silica gel, CH2Cl2: hexane 1:3) to give BODIPY1 (56 mg, 45.3%).
  • 47
  • [ 7697-46-3 ]
  • [ 142231-06-9 ]
YieldReaction ConditionsOperation in experiment
50.6% With copper dichloride In acetonitrile for 48h; Reflux; 2.10 Compound 8 To 200 mL of acetonitrile was added compound 7 (17 g, 0.083 mol) and 25 g of CuCl2, then the reaction mixture was heated to reflux with stirring for 48 h. After the reaction was cooled to room temperature, H2SO4 (10%, 101 mL) was added into reaction mixture, and the reaction keep stirring for 70 min. The resulting mixture was extracted by ethyl acetate (30 mL×3). The organic phase was washed by water (30 mL×3), then dried over Na2SO4 and evaporated in vacuum. The residue was purified by silica gel column (hexane:ethyl actate:DCM = 200: 1: 20) to afford 8 (8.6 g, 50.6%). 1H NMR (400MHz, CDCl3), δ 10.95 (s, 1H), 7.95 (d, 2H), 7.66 (t, 1H), 7.55 (t, 2H), 7.29 (s, 1H), 6.38 (s, 1H).
50% With copper(II) choride dihydrate In acetonitrile for 24h; Reflux;
  • 48
  • [ 7697-46-3 ]
  • 1,2-diphenyl-1,2-dipyrrolylethylene [ No CAS ]
  • 1,2-diphenyl-1,2-dipyrrolylethylene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; titanium tetrachloride; zinc In tetrahydrofuran; water for 5h; Inert atmosphere; Reflux; Overall yield = 44 percent; 1 [Production Example 1]Production of bispirol compound BP-Ph Zinc powder previously activated with 2 mass% hydrochloric acid under nitrogen atmosphere[Nacalai Tesque Co., Ltd., purity ≧ 85.0%] 12.4 g(190 mmol) was suspended in 285 g of dry THF.To this suspension, 18.4 g (96 mmol) of titanium tetrachloride [manufactured by Wako Pure Chemical Industries, Ltd.] was added dropwise at 0 ° C.After refluxing the reaction solution for 3 hours, 4.4 g (24 mmol) of 2-benzoylpyrrole [manufactured by Tokyo Chemical Industry Co., Ltd.]The solution dissolved in was dropped. The reaction was refluxed for 5 hours,1 mol / L sodium bicarbonate aqueous solution was added,The reaction was stopped. The organic layer is extracted with ethyl acetate, distilled water,After each washing with saturated saline,Dried over anhydrous sodium sulfate.The solvent was distilled off under reduced pressure to obtain a crude product.This crude product was purified by silica gel chromatography (dichloromethane-hexane (volume ratio 2: 8)),(E / Z) -BP-Ph1.6gWas obtained as a yellow solid (44% yield).
  • 49
  • [ 7697-46-3 ]
  • [ 373-68-2 ]
  • [ 37496-06-3 ]
YieldReaction ConditionsOperation in experiment
96% In toluene at 100℃; for 6h;
  • 50
  • [ 109-97-7 ]
  • [ 611-73-4 ]
  • [ 7697-46-3 ]
YieldReaction ConditionsOperation in experiment
91% With dipotassium peroxodisulfate In acetonitrile at 80℃; for 6h; Sealed tube; regioselective reaction;
80% With dipotassium peroxodisulfate; D-Glucose In water at 40℃; for 12h; Sealed tube;
  • 51
  • phenyl[1-(pyrimidin-2-yl)-1H-pyrrol-2-yl]methanone [ No CAS ]
  • [ 7697-46-3 ]
YieldReaction ConditionsOperation in experiment
90% With sodium ethanolate In dimethyl sulfoxide at 100℃; for 2.5h; Inert atmosphere;
  • 52
  • [ 7697-46-3 ]
  • C11H11N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrazine hydrate; acetic acid In toluene at 110℃; for 19h; 1.1 1) Weigh out 2-benzoylpyrrole (1.2mmol)And 87.98mmol hydrazine hydrate,Put it into a 100mL round bottom flask,30mL toluene dissolved,Add glacial acetic acid (0.02mmol) to catalyze,Heat to reflux at 110°C for 19 hours.After the reaction,The mixture was extracted with dichloromethane (40 mL×3 times),Wash the organic phase several times (to remove excess hydrazine hydrate),Dry with anhydrous sodium sulfate,Rotary steaming instrument to remove solvent,Compound C-1 was obtained.
  • 53
  • [ 7697-46-3 ]
  • 2,3,7,8-tetrafluoro-S-(trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate [ No CAS ]
  • phenyl[5-(trifluoromethyl)-1H-pyrrol-2-yl]methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With barium titanate In acetone for 3h; Milling;
  • 54
  • [ 7697-46-3 ]
  • [ 106-96-7 ]
  • [ 1437780-61-4 ]
YieldReaction ConditionsOperation in experiment
89% Stage #1: phenyl(1H-pyrrol-2-yl)methanone With potassium carbonate In N,N-dimethyl-formamide at 0℃; for 0.333333h; Stage #2: propargyl bromide In N,N-dimethyl-formamide at 20℃; for 16h; General procedure for the synthesisof the compounds 2a-2i General procedure: To a stirred mixture of 2-acylpyrroles 1a-1i (1 mmol) in 10cm3DMF was added K2CO3(2 mmol) at 0 °C. The reactionmixture was stirred at 0 °C for 20 min, and then propargylbromide (1.4 mmol) in 5 cm3DMF was added to the reactionflask dropwise over a period of 10 min. After stirring for16 h at room temperature, the resulting mixture was dilutedwith 20 cm3water and extracted with ethyl acetate (3 × 20cm3).The combined extracts were washed with brine (4 × 10cm3),dried with MgSO4,and filtered. The solvent was evaporated,and the crude product was purified over silica geleluting with hexane/EtOAc (5:1) to give 2a-2i.
  • 55
  • [ 7697-46-3 ]
  • [ 6279-86-3 ]
  • [ 108-24-7 ]
  • [ 140947-23-5 ]
YieldReaction ConditionsOperation in experiment
94.2% With sodium acetate; manganese(III) triacetate dihydrate; sodium hydrogensulfite In water; toluene 1 Example 1 Add 25 g of 2-benzoylpyrrole, 50.8 g of triethyl methanetricarboxylate, 58.7 g of manganese acetate dihydrate (trivalent), 24.0 g of sodium acetate, and 111.8 g of acetic anhydride into 250 mL of toluene, and heat to complete the reaction. , Add about 125mL of sodium bisulfite aqueous solution (add 2.5g of sodium bisulfite to 125mL of water for dissolution configuration), separate the liquids, after the organic phase is concentrated under reduced pressure, directly beaten with 50mL of isopropanol, filtered, and dried to obtain 55.2 g Diethyl 5-benzoyl-2,3-dihydro-1H-pyrrolazine-1,1-dicarboxylate (intermediate), yield 94.2%. Detected by HPLC, the purity of the intermediate is 99.733%, and the single largest impurity is 0.091%. The results are shown in Table 1 and Figure 1.
  • 56
  • [ 7697-46-3 ]
  • 2-azido-N-phenyl-N-butylacrylamide [ No CAS ]
  • N-butyl-N,1-diphenylpyrrolo[1,2-a]pyrazine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With Cs2CO3 In N,N-dimethyl-formamide at 20℃; for 48h; 3.2.4. Synthesis of N-butyl-N,1-diphenylpyrrolo[1,2-a]pyrazine-3-carboxamide (GML-23) 11.0 mmol (3.60 g) of cesium carbonate and 10.0 mmol(1.70 g) of phenyl(2H-pyrrol-2-yl)methanone were added to asolution of 10.0 mmol of 2-azido-N-phenyl-N-butylacrylamideamide in 15 ml of dry DMF and the reaction mixture was stirredat room temperature for two days. The resulting mixture wasdiluted with 30 ml of water, and the product was extracted with ethyl acetate 4 times with 20 ml. The combined organic solutions were washed with 20 ml of water, filtered through a paperfilter and evaporated to dryness. The residue was chromatographed on a silica gel column using ethyl acetate/hexane (2:3)as eluent. The product fractions were evaporated to dryness, the residue was recrystallized from ethanol to give pale yellow solid,yield 80%. M.p. 110-113°C. Found (%): C, 78.95; H, 6.40;N, 10.35. Calcd.(%): C, 78.02; H, 6.27; N, 11.37. 1H-NMR(DCl3, δ, ppm, J/Hz): 0.93 (t, 3 , 23, 3J = 7.3); 1.38 (m,2 , 23); 1.66 (m, 2 , 223); 3.98 (m, 2 ,N2); 6.90 (m, 1 , (8)); 6.94 (m, 1 , (7)); 7.18-7.55 (m,11 , 2 Ph, H(6)); 8.56 (s, 1 , (4)). IR (KBr), ν/sm-1: 3441(CON), 3076, 2955, 2870 (CH3, CH2-CH2-CH2), 1619 (C=O).
80% With Cs2CO3 In N,N-dimethyl-formamide at 20℃; for 48h; 3.2.4. Synthesis of N-butyl-N,1-diphenylpyrrolo[1,2-a]pyrazine-3-carboxamide (GML-23) 11.0 mmol (3.60 g) of cesium carbonate and 10.0 mmol(1.70 g) of phenyl(2H-pyrrol-2-yl)methanone were added to asolution of 10.0 mmol of 2-azido-N-phenyl-N-butylacrylamideamide in 15 ml of dry DMF and the reaction mixture was stirredat room temperature for two days. The resulting mixture wasdiluted with 30 ml of water, and the product was extracted with ethyl acetate 4 times with 20 ml. The combined organic solutions were washed with 20 ml of water, filtered through a paperfilter and evaporated to dryness. The residue was chromatographed on a silica gel column using ethyl acetate/hexane (2:3)as eluent. The product fractions were evaporated to dryness, the residue was recrystallized from ethanol to give pale yellow solid,yield 80%. M.p. 110-113°C. Found (%): C, 78.95; H, 6.40;N, 10.35. Calcd.(%): C, 78.02; H, 6.27; N, 11.37. 1H-NMR(DCl3, δ, ppm, J/Hz): 0.93 (t, 3 , 23, 3J = 7.3); 1.38 (m,2 , 23); 1.66 (m, 2 , 223); 3.98 (m, 2 ,N2); 6.90 (m, 1 , (8)); 6.94 (m, 1 , (7)); 7.18-7.55 (m,11 , 2 Ph, H(6)); 8.56 (s, 1 , (4)). IR (KBr), ν/sm-1: 3441(CON), 3076, 2955, 2870 (CH3, CH2-CH2-CH2), 1619 (C=O).
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