* 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.
Reference：
[1] Chemical & Pharmaceutical Bulletin, 1987, vol. 35, # 5, p. 1823 - 1828
2
[ 103-88-8 ]
[ 5304-21-2 ]
Reference：
[1] Chemische Berichte, 1928, vol. 61, p. 2070
3
[ 103-88-8 ]
[ 1575-37-7 ]
Reference：
[1] Justus Liebigs Annalen der Chemie, 1881, vol. 209, p. 358
4
[ 103-84-4 ]
[ 614-76-6 ]
[ 103-88-8 ]
Yield
Reaction Conditions
Operation in experiment
94%
With N-Bromosuccinimide; chloro-trimethyl-silane In acetonitrile at 20℃; for 1 h;
General procedure: To a solution of 4-bromoanisole (200.8 mg, 1.09 mmol, 1.0 equiv) in acetonitrile (2 mL) was added N-chlorosuccinimide(NCS) (158.3 mg, 1.19 mmol, 1.1 equiv) at rt to give a slightly cloudy mixture. Chlorotrimethylsilane (TMSCl) (14 μL, 0.11 mmol, 0.1 equiv) was then added drop-wise to the reaction mixture. Within a few minutes, the reaction mixture became clear pale yellow solution. The mixture continued to stir at rt for 1 h and was diluted with hexane. The biphasic mixture was concentrated on a rotary evaporator to a crude white solid-oil mixture. This mixture was taken up in hexane and filtered through a short plug of SiO2 and eluted with 5-10percent EtOAc-hexane solution. The clear filtrate was concentrated to obtain a mixture of 4-bromo-2-chloro-1-methoxybenzene (2a-Cl) and 2,4-dichloro-1-methoxybenzene (2a-diCl) 237.0 mg (88percent of 2a-Cl and 11percent of 2a-diCl,based on NMR ratio 2a-Cl: 2a-diCl = 7.1: 1.0; as a pale yellow solid).
Reference：
[1] Synlett, 2014, vol. 25, # 12, p. 1769 - 1775
[2] Journal of Organic Chemistry, 2018, vol. 83, # 2, p. 930 - 938
[3] Organic and Biomolecular Chemistry, 2018, vol. 16, # 30, p. 5433 - 5440
[4] Synthetic Communications, 2002, vol. 32, # 15, p. 2313 - 2318
[5] Synthetic Communications, 2002, vol. 32, # 15, p. 2313 - 2318
[6] Synthesis, 2002, # 2, p. 169 - 171
[7] Helvetica Chimica Acta, 2003, vol. 86, # 1, p. 164 - 168
[8] Synthetic Communications, 2004, vol. 34, # 12, p. 2143 - 2152
[9] Angewandte Chemie - International Edition, 2011, vol. 50, # 24, p. 5524 - 5527
[10] Chemical Communications, 2013, vol. 49, # 49, p. 5586 - 5588
5
[ 103-84-4 ]
[ 33098-80-5 ]
[ 614-76-6 ]
[ 103-88-8 ]
Reference：
[1] Angewandte Chemie - International Edition, 2011, vol. 50, # 24, p. 5524 - 5527
6
[ 103-84-4 ]
[ 614-76-6 ]
[ 103-88-8 ]
[ 23373-04-8 ]
Reference：
[1] Australian Journal of Chemistry, 2003, vol. 56, # 11, p. 1107 - 1111
[2] Dalton Transactions, 2010, vol. 39, # 43, p. 10464 - 10472
[3] Angewandte Chemie - International Edition, 2011, vol. 50, # 24, p. 5524 - 5527
Reference：
[1] Chemistry Letters, 2000, # 1, p. 48 - 49
[2] Synthetic Communications, 2001, vol. 31, # 7, p. 1123 - 1127
[3] Tetrahedron, 2003, vol. 59, # 3, p. 287 - 293
[4] Organic and Biomolecular Chemistry, 2018, vol. 16, # 21, p. 3881 - 3884
[5] Collection of Czechoslovak Chemical Communications, 1935, vol. 7, p. 436,443
[6] Justus Liebigs Annalen der Chemie, 1881, vol. 209, p. 358
[7] Journal of the Chemical Society, 1924, vol. 125, p. 940,941
[8] Chemical & Pharmaceutical Bulletin, 1987, vol. 35, # 5, p. 1823 - 1828
[9] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 20, p. 2747 - 2750
[10] Journal of Medicinal Chemistry, 2012, vol. 55, # 13, p. 6047 - 6060
10
[ 103-88-8 ]
[ 3460-23-9 ]
Reference：
[1] Synthetic Communications, 2012, vol. 42, # 24, p. 3655 - 3663,9
[2] European Journal of Organic Chemistry, 2018, vol. 2018, # 34, p. 4748 - 4753
[3] Chemistry - A European Journal, 2017, vol. 23, # 29, p. 7031 - 7036
[4] Organic and Biomolecular Chemistry, 2018, vol. 16, # 30, p. 5433 - 5440
[5] Journal of the Indian Chemical Society, 1981, vol. 58, p. 447 - 453
[6] Journal of the Chemical Society, 1907, vol. 91, p. 1567
[7] Journal of the Chemical Society, 1916, vol. 109, p. 96
[8] Journal of the Chemical Society, 1923, vol. 123, p. 3394
11
[ 7647-01-0 ]
[ 103-88-8 ]
[ 127-65-1 ]
[ 3460-23-9 ]
Reference：
[1] Journal of the Chemical Society, 1923, vol. 123, p. 3394
12
[ 103-88-8 ]
[ 108-95-2 ]
[ 6312-87-4 ]
Reference：
[1] Journal of Organic Chemistry, 2009, vol. 74, # 18, p. 7187 - 7190
[2] Organic Letters, 2012, vol. 14, # 1, p. 170 - 173
[3] Organic Letters, 2008, vol. 10, # 20, p. 4565 - 4568
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; triethylamine In 1,4-dioxane at 20 - 100℃; Inert atmosphere
To a solution of compound 47 (250 mg, 1.45 mmol) in dioxane(6 mL) at room temperature was added bis(pinacolato)diboron(554 g, 2.18 mmol, 1.5 equiv.), and KOAc (427 mg, 4.35 mmol, 3equiv.). The reaction mixture was degassed under N2. Pd(dppf)Cl2(90 mg, 0.12 mmol, 0.1 equiv.) was added to the mixture anddegassed under N2. The reaction mixture was heated to 100 C andstirred overnight under nitrogen. The reaction mixture was monitoredusing TLC until completion, filtered through Celite andwashed with EA. The reaction solvent was evaporated underreduced pressure to give a residue, which was purified via silica gelcolumn chromatography (elution system - EA/Hexane 1: 1) togive compound 48 as a white solid (870 mg, 71percent).Rf 0.43 (EA/Hexane 1: 1); 1H NMR (400 MHz, CDCl3) d 7.76(d, J 8.3 Hz, 2H), 7.51 (d, J 7.9 Hz, 2H), 7.19 (s, 1H), 2.18 (s, 3H),1.33 (s, 12H).
Reference：
[1] European Journal of Medicinal Chemistry, 2018, vol. 158, p. 593 - 619
[2] European Journal of Medicinal Chemistry, 2015, vol. 96, p. 382 - 395
(i) N-(4-Bromophenyl)acetamide Triethylamine (0.65 ml, 4.65 mmol) was added to a solution of 200 mg (1.16 mmol) of 4-bromoaniline in tetrahydrofuran (2 ml), and the mixture was stirred at room temperature for 5 min. Acetyl chloride (0.165 ml, 2.33 mmol) was added thereto, and the mixture was stirred at room temperature for 17 hr. The reaction was stopped by adding a saturated aqueous sodium hydrogencarbonate solution, and the reaction solution was extracted with ethyl acetate. The organic layer was washed with water and saturated brine in that order, was dried over anhydrous sodium sulfate and was filtered. The filtrate was concentrated under the reduced pressure, and the residue was purified by column chromatography on silica gel (chloroform: methanol = 20: 1) to give 249 mg (yield 99%) of the title compound.
94%
To a stirred solution of 4-bromoaniline (30 g, 174 mmol) in dichioromethane (150 mL) was added triethylamine (73.53 mL, 523 mmol) at 0 C and the mixture was stirred for 15 mm. To this mixture was added acetyl chloride (19.12 g, 240mmol) dropwise and the mixture was stirred at room temperature overnight. The reaction was quenched by addition of water (100 mL). The organic layer was separated, washed with brine solution (100 mL), dried over sodium sulfate, and concentrated under reduced pressure to afford N-(4-bromophenyl)acetamide (35 g, 94% yield): ?H NMR (400 MHz, DMSO-d6) oe 10.05 (s, 1 H), 7.55 (d, J 9.2 Hz, 2H), 7.46 (dd, J= 2 Hz, 6.4 Hz, 2 H), 2.05 (s, 3 H).
94%
With hydroxyapatite supported copper(I) oxide; In acetonitrile; at 50℃; for 0.166667h;
General procedure: To a mixture of amine (1 mmol), acetyl chloride (1 mmol)in acetonitrile (5 mL) were added hydroxyapatite -Cu2O(0.1 g) under air atmosphere. The reaction mixture wasrefluxed at 50 C for an appropriate time. The progress ofthe reaction was monitored through TLC. Upon completionof the reaction, the reaction mixture was cooled toroom temperature and filtered. The residue was washedwith water followed by EtOAc (3 × 10 mL). The productwas obtained after the removal of solvent under reducedpressure followed by crystallization from pet ether orEtOAc:pet ether or passing through column of silica andelution with EtOAc:pet ether.
89%
With potassium carbonate; In dichloromethane; at 20℃; for 3h;
To the solution of 4-bromoaniline (46) (2.5 g, 14.5 mmol, 1equiv.) and potassium carbonate (6.05 g, 43.78 mmol, 3 equiv.) indichloromethane (50 mL) was added acetyl chloride (1.55 mL, 2equiv.). The solution was stirred at ambient temperature until TLCshowed the consumption of the starting material. Acetyl chlorideand DCM were evaporated under reduced pressure at 45 C. Waterwas added to dissolve the salt in the residue. The residue mixturewas filtered and washed with DCM. The product (47) was driedunder vacuum to give a light grey solid (2.78 g, 89%) which wasdirectly used in the next step without further purification.Rf 0.22 (EA/Hexane 1: 1); 1H NMR (400 MHz, CDCl3)d 7.49e7.34 (m, 4H), 7.17 (s, 1H), 2.17 (s, 3H).
46%
With triethylamine; In dichloromethane; at 0℃; for 2h;
Step 56a: N-(4-bromophenyl)acetamide (Compound 0601-150)To the solution of 4-bromoaniline (6.3 g, 63.7mmol) in CH2C12 (50 mL) was added acetyl chloride (3.75 g, 47.7 mmol) and TEA (7.4 g, 73.4 mmol) at 0 C, stirred for 2 hours.The reaction mixture was washed with water, brine , dried over Na2S04, filtered, and concentrated under reduced pressure to give the title compound 0601-150 (3.6 g, 46%>) as a brown solid. LCMS: 214 [M+l]+; 1H NMR (400 MHz, DMSO-d6). delta 2.05 (s, 3H), 7.46(d, J= 8.8 Hz, 2H), 7.57 (d, J= 8.8 Hz, 2H), 10.12 (s, 1H).
46%
With triethylamine; In dichloromethane; at 0℃; for 2h;
Step 56a: N-(4-bromophenyl)acetamide (Compound 0601-150)[0434]To the solution of 4-bromoaniline (6.3 g, 63.7 mmol) in CH2Cl2 (50 mL) was added acetyl chloride (3.75 g, 47.7 mmol) and TEA (7.4 g, 73.4 mmol) at 0 C., stirred for 2 hours. The reaction mixture was washed with water, brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give the title compound 0601-150 (3.6 g, 46%) as a brown solid. LCMS: 214 [M+1]+; 1H NMR (400 MHz, DMSO-d6). delta 2.05 (s, 3H), 7.46 (d, J=8.8 Hz, 2H), 7.57 (d, J=8.8 Hz, 2H), 10.12 (s, 1H).
46%
With triethylamine; In dichloromethane; at 0℃; for 2h;
CH2Cl2 (50mL) solution of 4-bromo-aniline (6.3g, 63.7mmol) in concentrated solution, with the addition of acetyl chloride (3.75g, 47.7mmol) and TEA the (7.4g, 73.4mmol) at 0 , 2 hours with stirring did. The reaction mixture was washed with water, brine, dried over Na2SO4, filtered and concentrated in vacuo to give the title compound 0601-150 as a brown solid (3.6g, 46%).
46%
With triethylamine; In dichloromethane; at 0℃; for 2h;
To the solution of 4-bromoaniline (6.3 g, 63.7mmol) in CH2C12 (50 mL) was addedacetyl chloride (3.75 g, 47.7 mmol) and TEA (7.4 g, 73.4 mmol) at 0 C, stirred for 2hours. The reaction mixture was washed with water, brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give the title compound 0601-150 (3.6 g, 46%) as a brown solid. LCMS: 214 [M+lf?; ?H NMR (400 MI-Tz, DMSO-d6). 2.05 (s, 3H), 7.46 (d, J 8.8 Hz, 2H), 7.57 (d, J 8.8 Hz, 2H), 10.12 (s, 1H).
46%
With triethylamine; In dichloromethane; at 0℃; for 2h;
To the solution of 4-bromoaniline (6.3 g, 63.7 mmol) in CH2Cl2 (50 mL) was added acetyl chloride (3.75 g, 47.7 mmol) and TEA (7.4 g, 73.4 mmol) at 0 C., stirred for 2 hours. The reaction mixture was washed with water, brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give the title compound 0601-150 (3.6 g, 46%) as a brown solid. LCMS: 214 [M+1]+1H NMR (400 MHz, DMSO-d6). delta 2.05 (s, 3H), 7.46 (d, J=8.8 Hz, 2H), 7.57 (d, J=8.8 Hz, 2H), 10.12 (s, 1H).
With triethylamine; In dichloromethane; at 20℃;
General procedure: 1.607g was added to a 100mL round bottom flask with a magnetic stir bar.15.0 mmol of toluidine, 50.0 mL of CH 2 Cl 2 and 4.170 mL, 30.0 mmol of Et 3 N,Finally, 1.273 mL, 18.0 mmol of acetyl chloride was added, and the reaction mixture was stirred at room temperature with a magnetic stirrer;TLC showed that after the consumption of p-toluidine was completed, the reaction was quenched with 100 mL of saturated NaHCO3 solution.It was then extracted 3 times with 100.0 mL of CH 2 Cl 2 and the combined organic phases were washed twice with 50 mL of brine.The solid obtained by distilling off the organic solvent was washed with a 5:1 mixture of petroleum ether/ethyl acetate to give a white solid p-methylacetanilide;
5.8 g
With triethylamine; In dichloromethane; at 20℃;Cooling with ice; Inert atmosphere;
4-Bromoaniline (5.0 g, 29.1 mmol, CAS: 106-40-1) was dissolved in 80 mL of dichloromethane and 8.1 mL of triethylamine was added. After cooling in an ice water bath, acetyl chloride (2.74 g, 34.9 mmol) was slowly added dropwise under the protection of argon. After the addition was completed, the mixture was allowed to warm to room temperature and stirred overnight.Add 80 mL of water, extract three times with DCM, combine the organic phases, and wash three times with saturated brine.Dry over anhydrous sodium sulfate and remove the solvent by rotary evaporation in vacuo.Purification by silica gel column chromatography gave Intermediate E23-1 (5.8 g).
General procedure: Polystyrene-supported phosphine oxide (10.4 mg, 2.5 mol%), (E)-1-Phenylethan-1-one oxime 1a (67.5 mg, 0.5 mmol) and HFIP (2 mL) were added to a 10-mL glass vessel containing a magnetic stirring bar. Then, oxalyl chloride (64.8 mg, 0.5 mmol) was added at 0 C. The mixture was stirred at room temperature for 2 h. After completion of the reaction (indicated by TLC), the catalyst was removed by filtration and the solvent was removed under reduced pressure. The crude material was purified by silica gel column using PE/EtOAc as the eluent to afford the desired product 2a in 99% yield.
88%
With titanium cation-exchanged montmorillonite; In benzonitrile; at 90℃; for 18h;Inert atmosphere;
General procedure: A typical procedure for the Beckmann rearrangement of 1 by Ti4+-mont is as follows. Ti4+-mont (0.10 g) was placed in a reaction vessel, followed by addition of benzonitrile (5 mL) and 1 (1 mmol). The reaction mixture was vigorously stirred at 90 C under Ar for 3 h. After the reaction, the mixture was centrifuged, and the supernatant was analyzed by GC with naphthalene as an internal standard to determine the conversion and yield.
86%
With carbon tetrabromide; Eosin Y; N,N-dimethyl-formamide; In acetonitrile; at 20℃; for 16h;Irradiation; Inert atmosphere; Green chemistry;
General procedure: A mixture of ketoxime 1 (1.0 mmol), CBr4 (2.0 equiv), eosin Y (2 mol%), DMF (20 mol%) and MeCN (3 mL) was taken in a hot oven dried round bottom flask and irradiated with green LEDs under a nitrogen atmosphere. After completion of the reaction as indicated by TLC, it was quenched with saturated aqueous sodium hydrogen carbonate (10 mL) and extracted with ethyl acetate (3 × 10 mL). The organic phase was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to yield the crude product, which was purified by silica gel column chromatography (EtOAc-hexane) to give the corresponding amide 2 in high yield. All the products are known compounds and were characterized by comparison of their mp, TLC, 1HNMR, 13C NMR and MS data with authentic samples obtained commercially or prepared byliterature methods.
72%
With iron(III) chloride; silver hexafluoroantimonate; In 1,2-dichloro-ethane; at 80℃; for 24h;
General procedure: To an oven-dried 20 mL vial containing FeCl3 (24.3 mg,0.15 equiv), was added a solution of oxime (1 mmol) in DCE (10mL) and the mixture was stirred until FeCl3 was completely dissolved(10-15 min). To this solution was added AgSbF6 (154.6mg, 0.45 equiv), then the vial was capped and put into mechanicalshaker at 80 C for 24 h. The mixture was filtered throughCelite with CH2Cl2 (100 mL) and concentrated to give a residue,which was purified by silica flash chromatography usinghexanes and ethyl acetate in appropriate combination based onthe Rf of the desired product.
With 7,7-dichlorocyclohepta-1,3,5-triene; In acetonitrile; at 80℃;Schlenk technique; Inert atmosphere;
In a 50 ml three neck round bottom flask,After adding 0.214 g of p-bromoacetophenone oxime and 8 mg of 1,1-dichloroheptatriene,Even a ball condenser,On schlenk,Suction and ventilation 3 times,N2 system to maintain the atmosphere,Then 10 ml of acetonitrile was added,Stirring and heating to 80 reflux reaction,The reaction was followed by liquid chromatography (after the sample was added a small amount of acetic acid in the sampleEster dilution):3h when the conversion of raw materials 22%24h fully converted raw materials,Acetylacetophenone target product selectivity of> 98%.After the reaction was completed, the solvent was distilled off under reduced pressure,By rapid preparative chromatography,Pure acetyl p-methylaniline was obtained,White solid.
With hydroxylamine hydrochloride; water; Thiamine hydrochloride; In 1,4-dioxane; at 90℃; for 0.5h;
General procedure: A mixture of ketone 1 (2 mM), hydroxylamine hydrochloride (3 mM) and thiamine hydrochloride (0.4 mM) was taken in 10mL dioxane:H2O (9:1) in a round-bottom flask and heated at 90 C for specific time (30-90 min). The progress of the reaction was monitored using thin layer chromatography (tlc). After completion of the reaction, the reaction flask was cooled to room temperature. The residue was taken in ethyl acetate (30 ml), washed with water (2x15 ml), brine (1x15 ml) and the organic layer was dried (anhyd. Na2SO4). The resulting ethyl acetate solution was concentrated and the desired amides 2 (75-95% yield) are obtained by recrystallization from ethanol.
90%
With mesitylenesulfonylhydroxylamine; In acetonitrile; at 20℃; for 8h;
General procedure: To a round bottom flask, equipped with a magnetic stirring bar, was added ketone 1 (0.5 mmol, 1.0 equiv.) and acetonitrile (2 mL) at room temperature. To this stirred solution, freshly prepared O-(Mesitylsulfonyl)hydroxylamine 2 (2.0 equiv.) was added. The reaction mixture was stirred for the specified duration and temperature. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was diluted with ethyl acetate (10 mL) and washed with a saturated aqueous NaHCO3 solution (3 x 5 mL). The combined organic layer was washed with brine solution and dried over anhydrous Na2SO4. Solvent was removed under reduced pressure to get the crude product. The reaction that required elevated temperature was stirred first at room temperature for 2 hours after addition of MSH and then heated at 70 C for the specified time.
88%
With hydroxylamine hydrochloride; In acetonitrile;Reflux;
General procedure: Ketones (1 mmol) and hydroxylamine hydrochloride (0.0694g,1 mmol) were dissolved in CH3CN (10 mL) and stirred for 10 - 15 min. The complex (CS-SalBr-Zn-L) (10 mol%) were added tothe reaction flask. The reaction mixture was heated under reflux for specific time (3e7 h). After completion, the reaction mixture was cooled to room temperature and the catalyst was removed by filtration. The filtrate was treated with ethyl acetate (3 10 mL).The combined organic layers were treated with saturated brine solution and dried over anhydrous sodium sulphate. The removal of solvent yields crude product, which after purification by column chromatography over Silica gel (100e200 mesh), afforded the desired products.
With N-Bromosuccinimide; chloro-trimethyl-silane; In acetonitrile; at 20℃; for 1h;
General procedure: To a solution of 4-bromoanisole (200.8 mg, 1.09 mmol, 1.0 equiv) in acetonitrile (2 mL) was added N-chlorosuccinimide(NCS) (158.3 mg, 1.19 mmol, 1.1 equiv) at rt to give a slightly cloudy mixture. Chlorotrimethylsilane (TMSCl) (14 muL, 0.11 mmol, 0.1 equiv) was then added drop-wise to the reaction mixture. Within a few minutes, the reaction mixture became clear pale yellow solution. The mixture continued to stir at rt for 1 h and was diluted with hexane. The biphasic mixture was concentrated on a rotary evaporator to a crude white solid-oil mixture. This mixture was taken up in hexane and filtered through a short plug of SiO2 and eluted with 5-10% EtOAc-hexane solution. The clear filtrate was concentrated to obtain a mixture of 4-bromo-2-chloro-1-methoxybenzene (2a-Cl) and 2,4-dichloro-1-methoxybenzene (2a-diCl) 237.0 mg (88% of 2a-Cl and 11% of 2a-diCl,based on NMR ratio 2a-Cl: 2a-diCl = 7.1: 1.0; as a pale yellow solid).
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; In tetrahydrofuran; ethyl acetate; at 70℃; for 2h;Inert atmosphere;
To a solution of ketoxime (0.01 mol) in THF (10 mL) was added T3P (15 mol %, 50% soln in EtOAc) and the resulting reaction mixture was stirred at reflux for 1-4 h under nitrogen atmosphere. When the reaction was completed as confirmed by TLC, the solvent was removed under vacuum and the residue was diluted with water (20 mL). The product was extracted with ethyl acetate (2 × 20 mL) and the combined organic phase was washed with saturated NaHCO3 solution (1 × 10 mL) and brine. The organic phase was dried over anhydrous Na2SO4. The solvent was removed under reduced pressure to afford the desired amides in good purity.
33%
With phthalic anhydride; zinc trifluoromethanesulfonate; In acetonitrile; at 50℃;Inert atmosphere;
General procedure: Oxime 1 (1.0 mmol, 1.0 equiv), Zn(OTf)2 (73.7 mg, 0.2 mmol, 0.2 equiv) and o-phthalic anhydride (15.0 mg, 0.1 mmol, 0.1 equiv) were dissolved in 1.0 mL CH3CN at rt under nitrogen atomesphere and stirred until the complete consumption of the oxime monitored by TLC analysis. The mixture was evaporated and the residue was purified on flash column chromatography with petroleum ether/ethyl acetate (5:1~2:1) as eluent to afford the desired amide 2.
General procedure: A mixture of carboxylic acid (1 mmol) and TAPC (0.5 mmol, 0.17 g) was grinded at room temperature for 1 min. Then amine (1mmol) was added to the reaction mixture and grinding was continued at the sametemperature for the specified time (Table 2). The progress of the reaction wasmonitored by TLC. After completion of the reaction, H2O (10 mL) wasadded to the reaction mixture and filtered. The product was recrystallized fromEtOH/H2O to afford the pure product.
96%
With poly(4-vinylpyridine) perchlorate; In neat (no solvent); at 20℃; for 0.3h;
General procedure: The substrate (alcohol, phenol or amine; 1.0 mmol) was treated with Ac2O (2.0 mmol) in the presence of P(4-VPH)ClO4 (50 mg) at room temperature under solvent-free conditions and magnetic stirring. After completion of the reaction as indicated by TLC, the mixture was diluted with Et2O (25 ml) and the catalyst allowed to settle down. The supernatant ethereal solution was decanted off, the catalyst washed with Et2O (2 ml) and the combined ethereal solution concentrated under vacuum to afford the product, identical(mp, IR, 1H and 13C NMR, and GC-MS) to an authentic sample of acetylated product. The recovered catalyst was dried at 50 C under vacuum for 2 h. The recovered catalyst, after drying, was reused for four more consecutive acetylation reactions of benzyl alcohol (1.0 mmol) affording 96, 96, 94, and 94% yields, respectively, in 22, 23, 23, and 25 min (Scheme 2).
(ii) N-(4-Bromophenyl)-N-methylacetamide Sodium hydride (101.5 mg, 2.33 mmol) (55% in paraffin liquid) was added to a solution of 249 mg (1.16 mmol) of the title compound produced in step (i) of Reference Example 7 in N,N-dimethylformamide (2.5 ml), and the mixture was stirred at room temperature for 30 min. Thereafter, methyl iodide was added, and the mixture was stirred at room temperature for 1 hr. The reaction was stopped by adding a saturated aqueous sodium hydrogencarbonate solution, and the reaction solution was extracted with ethyl acetate. The organic layer was washed with water and saturated brine in that order, was dried over anhydrous sodium sulfate, and was filtered. The filtrate was concentrated under the reduced pressure, and the residue was purified by column chromatography on silica gel (hexane : ethyl acetate = 2 : 1) to give 239 mg (yield 90%) of the title compound. 1H-NMR (400 MHz, CDCl3) delta: 1.88 (3H, s), 3.24 (3H, s), 7.08 (2H, d, J = 8.5 Hz), 7.54 (2H, d, J = 8.5 Hz). MS (FAB+) m/z: 227 (M+ + 1).
74%
N-(4-Bromophenyl)-7V-methyl-acetamide (62) EPO <DP n="237"/><strong>[103-88-8]4-bromoacetanilide</strong> (1.0 g, 4.67 mmol) in DMF (5 mL) is added dropwise to a suspension of sodium hydride (224 mg, 5.61 mmol, 60% dispersion in mineral oil) in DMF (5 mL) at 0C. After stirring 1 h at 0C, iodomethane (349 mul, 5.61 mmol) is added and the reaction mixture warmed to RT and stirred 16 h. The reaction is quenched with water (15 mL) and extracted into EtOAc (3 x 15 mL); the combined organic phases are then dried over Na2SO4 and reduced in vacuo. Purification by column chromatography (40% EtOAc in heptane) gives the title compound. Yield: 780 mg (74%).LC/MS tr 1.17 min. MS(ES+) m/z 230, 228 (M+H
74%
Synthesis of Compound 318lambdaf-(4-Bromophenyl)-lambda''-methyl-acetamide (62)<strong>[103-88-8]4-bromoacetanilide</strong> (1.0 g, 4.67 mmol) in DMF (5 mL) was added dropwise to a suspension of sodium hydride (224 mg, 5.61 mmol, 60% dispersion in mineral oil) in DMF (5 mL) at 0C. After stirring 1 h at 0C, iodomethane (349 mul, 5.61 mmol) <n="149"/>was added and the reaction mixture warmed to RT and stirred 16 h. The reaction was quenched with water (15 mL) and extracted into EtOAc (3 x 15 mL); the combined organic phases were then dried over Na2SO4 and reduced in vacuo. Purification by column chromatography (40% EtOAc in heptane) gave the title compound.Yield: 780 mg (74%).LCZMS f1. 1.17 min.MS(ES+) m/z 230, 228 (M+H).
74%
JV-(4-Bromophenyl)-7V-methyl-acetamide (62); EPO <DP n="237"/><strong>[103-88-8]4-bromoacetanilide</strong> (1.0 g, 4.67 mmol) in DMF (5 mL) is added dropwise to a suspension of sodium hydride (224 mg, 5.61 mmol, 60% dispersion in mineral oil) in DMF (5 mL) at 0C. After stirring 1 h at 0C, iodomethane (349 mul, 5.61 mmol) is added and the reaction mixture warmed to RT and stirred 16 h. The reaction is quenched with water (15 mL) and extracted into EtOAc (3 x 15 mL); the combined organic phases are then dried over Na2SO4 and reduced in vacuo. Purification by column chromatography (40% EtOAc in heptane) gives the title compound. Yield: 780 mg (74%). LC/MS fr 1.17 min. MS(ES+) m/z 230, 228 (M+H).
74%
Synthesis of Compound 318; yV-(4-Bromophenyl)-7V-methyl-acetamide (62); <strong>[103-88-8]4-bromoacetanilide</strong> (1.0 g, 4.67 mmol) in DMF (5 mL) is added dropwise to a suspension of sodium hydride (224 mg, 5.61 mmol, 60% dispersion in mineral oil) in DMF (5 mL) at 0C. After stirring 1 h at 0C, iodomethane (349 mul, 5.61 mmol) is added and the reaction mixture warmed to RT and stirred 16 h. The reaction is quenched with water (15 mL) and extracted into EtOAc (3 x 15 mL); the combined organic phases are then dried over Na2SO4 and reduced in vacuo. Purification by column chromatography (40% EtOAc in heptane) gives the title compound. Yield: 780 mg (74%).LC/MS ;r 1.17 min. MS(ES+) m/z 230, 228 (M+H).
With potassium phosphate In N,N-dimethyl-formamide at 100℃; for 20h;
91%
With potassium phosphate; copper(l) iodide; glycine In 1,4-dioxane at 100℃; for 24h;
90%
With aluminum oxide; potassium fluoride; copper(l) iodide; 1,10-Phenanthroline In toluene at 110℃; for 11h;
75%
With copper(I) thiophene-2-carboxylate; sodium t-butanolate In dimethyl sulfoxide at 100℃; for 6h; Inert atmosphere;
70%
With copper(ll) sulfate pentahydrate; sodium ascorbate; sodium t-butanolate In dimethyl sulfoxide at 100℃; for 7h;
1 General procedure for N-arylation of primary amides
General procedure: CuSO4*5H2O (0.15 mmol), NaAsc (0.3 mmol), aryl iodides (1mmol), primary amides (1.2mmol), t-BuONa (2.0 mmol), and DMSO (3mL) were added to a flask. The reaction mixture was stirred under air, and then cooled to room temperature and extracted with ethyl acetate (3×10 mL). The organic layer was then dried over anhydrous Na2SO4, and the solvent was removed under reduced pressure. The secondary amides were finally obtained by column chromatography on silica gel eluted with ethyl acetate/petroleum ether.
With potassium phosphate; copper(l) iodide; dimethylaminoacetic acid In dimethyl sulfoxide at 80℃; for 24h; Inert atmosphere;
With potassium fluoride;palladium diacetate; In tetrahydrofuran;
EXAMPLE 38 Synthesis of N-acetyl-4-aminobiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.02 mmol, 2.0 mol percent), phenylboronic acid (183 mg, 1.5 mmol), potassium fluoride (174 mg, 3.0 mmol), and 4'-bromoacetanilide (214 mg, 1.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) was added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl bromide had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL), filtered through celite, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 182 mg (86percent) of the title compound.
182 mg (86%)
With potassium fluoride;palladium diacetate; In tetrahydrofuran;
Example 38 Synthesis of N-acetyl-4-aminobiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.02 mmol, 2.0 mol percent), phenylboronic acid (183 mg, 1.5 mmol), potassium fluoride (174 mg, 3.0 mmol), and 4'-bromoacetanilide (214 mg, 1.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) was added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl bromide had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL), filtered through celite, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 182 mg (86percent) of the title compound.
A microwave vessel was charged with 4'-bromoacetoanilide (1.19 g, 5.56 mmol), 2,2,6, 6-tetramethyl-3,5-heptanedione (0.23 mL, 1.1 mmol), copper(I) chloride (0.22 g, 2.2 mmol), cesium carbonate (5.42 g, 16.7 mmol), 4-fluoro-2- methylphenol (0.70 g, 5.6 mmol), and JV-methyl-2-pyrrolidone (5 niL). The reaction mixture was heated at 200 0C in a microwave oven for 20 minutes. The reaction mixture then was cooled to ambient temperature and diluted with deionized water (20 mL). The dilution was extracted with ethyl acetate (20 mL) and the extract combined with saturated sodium bicarbonate (aq., 100 mL). The mixture was washed with brine (30 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The residue was diluted with concentrated hydrochloric acid (15 mL) and the dilution was heated at 100 0C for 2 hours. The reaction mixture was cooled to ambient temperature and diluted with 4N sodium hydroxide until basic. The dilution was extracted with methylene chloride (30 mL) and the extract was washed with brine (30 mL), dried over anhydrous sodium sulfate, filtered and concentrated. Product was purified from the residue by reverse phase HPLC to give 4-(4-fluoro-2- methylphenoxy)aniline (0.33 g, 1.5 mmol, 27% yield) as off-white solid. MS (EI) for C13H12FNO, found 218.1 (MH+).
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In ethanol at 80℃; for 2h; Inert atmosphere;
General procedure: General procedure: The synthetic procedure for pentafluorophenyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonate (a) is presented as an example (Scheme 1). 2,2'-Bis(1,3,2-benzodioxaborole) (cat2B2, 262 mg, 1.10 mmol), PdCl2(dppf) (25 mg, 0.030 mmol), AcOK (294 mg, 3.0 mmol), pentafluorophenyl 4-bromobenzenesulfonate (403 mg, 1.0 mmol), and EtOH (6.0 mL) were charged in a reaction vessel under an Ar atmosphere. The resulting mixture was stirred for 2 h at 80 °C. After cooling to room temperature, pinacol (260 mg, 2.20 mmol) was added to the mixture. The mixture was further stirred for 30 min at room temperature. H2O and n-hexane were added to the mixture and the product was extracted into the organic layer. After drying the organic layer with anhydrous MgSO4, solids were removed by filtration. The filtrate was concentrated. The product was obtained as a white solid by Kugelrohr distillation.
With trimethylsilylazide; silver carbonate; trifluoroacetic acid In water; 1,2-dichloro-ethane at 60℃; for 12h; Schlenk technique; Inert atmosphere;
93%
With (triphenylphosphine)gold(I) chloride; trimethylsilylazide; water; silver carbonate; trifluoroacetic acid In 1,2-dichloro-ethane at 60℃; Schlenk technique; Inert atmosphere;
85%
With sodium azide; C16H17AuBrN3O; water; trifluoroacetic acid In 1,2-dichloro-ethane at 25℃; for 2h; Schlenk technique; Inert atmosphere; regioselective reaction;
6.3. General procedure for catalysis
General procedure: Alkynes (0.5 mmol), NaN3 (1 mmol), H2O (1 mmol), catalyst 1(2 mol%) and TFA/DCE (2 mL, 1:1 v/v) were taken in a Schlenk tube inside a fume hood. The reaction mixture was allowed to stir for 2 h at room temperature. Then 25 mL water was added to it and theorganics were extracted with ethyl acetate (3 x 10 mL). The solventwas evaporated under reduced pressure. The residue was purifiedby column chromatography on silica gel (petroleum ether/ethylacetate) to give the desired amide product. Yields were calculatedbased on isolated products. GC yields were reported in presence ofinternal standard dodecane.
62%
With formic acid; nitromethane; trifluoromethylsulfonic anhydride In acetic acid at 100℃; for 12h;
1-(5-bromo-2-methyl-1H-indol-1-yl)ethanone[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
79%
With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate; silver carbonate In 1,4-dioxane at 110℃; for 24h; Schlenk technique; Inert atmosphere;
A. General Procedure for Rhodium-Catalyzed Indoles Synthesis
General procedure: A 10 mL Schlenk tube equipped with a magnetic stirrer was charged with [Rh Cp* Cl2]2 (5 mol%), AgSbF6 (20 mol%), Cu(OAc)2 (1equiv), Ag2CO3(1equiv),and substituted acetanilideas 1 (0.2 mmol). The tube wasevacuated and backfilled with argon for three times. Then allyl carbonate (0.4 mmol) in dioxane (1 mL) was added. After addition of all substrates, the reactionmixture was stirred and heated at 110°Cfor 24h. Then reaction was cooled to room temperature. Solvent and volatile reagents were removed by rotary evaporation and theresidue was purified by flash column chromatography on silica gel to give the target product
With carbon monoxide; palladium diacetate In acetonitrile at 60℃;
4.5 General procedure for the synthesis of acetanilides from guanidines
General procedure: To a screw-cap reaction tube was added symmetrical N,N′-disubstituted guanidines 1a (0.2 mmol), Pd(OAc)2 (5 mol%, 2.2 mg), Cu(OAc)2 (0.2 mmol, 36.3 mg). The reaction tube was evacuated and back-filled with CO (three times, balloon). MeCN (2mL) was added using a syringe and the mixture was heated to the desired temperature with use of an oil bath. When the reaction was completed (detected by TLC), the mixture was cooled to room temperature and vented to discharge the excess CO. The solvent was concentrated by evaporation in vacuo. The residue was purified by flash column chromatography on silica gel to afford the desired product amides 2a with petroleum ether/ethyl acetate as the eluent.
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; triethylamine; In 1,4-dioxane; at 20 - 100℃;Inert atmosphere;
To a solution of compound 47 (250 mg, 1.45 mmol) in dioxane(6 mL) at room temperature was added bis(pinacolato)diboron(554 g, 2.18 mmol, 1.5 equiv.), and KOAc (427 mg, 4.35 mmol, 3equiv.). The reaction mixture was degassed under N2. Pd(dppf)Cl2(90 mg, 0.12 mmol, 0.1 equiv.) was added to the mixture anddegassed under N2. The reaction mixture was heated to 100 C andstirred overnight under nitrogen. The reaction mixture was monitoredusing TLC until completion, filtered through Celite andwashed with EA. The reaction solvent was evaporated underreduced pressure to give a residue, which was purified via silica gelcolumn chromatography (elution system - EA/Hexane 1: 1) togive compound 48 as a white solid (870 mg, 71%).Rf 0.43 (EA/Hexane 1: 1); 1H NMR (400 MHz, CDCl3) d 7.76(d, J 8.3 Hz, 2H), 7.51 (d, J 7.9 Hz, 2H), 7.19 (s, 1H), 2.18 (s, 3H),1.33 (s, 12H).
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; for 2h;Reflux; Inert atmosphere;
General procedure: A mixture of substituted 3-(or 4-) bromobenzamides or 3-bromobenzoate or N-(3-(or 4-)bromophenyl)acetamide 3, (0.5 mmol), bis(pinacolato)diboron (0.14 g, 0.55 mmol), potassium acetate (0.15 g, 1.5 mmol), PdCl2(dppf) (0.03 g, 0.04 mmol) and 1,4-dioxane (10 mL) was refluxed for 2 h under nitrogen atmosphere. The solvent was evaporated under reduced pressure to afford a dark brown residue. To the residue was added intermediate 2 (0.4 mmol), sodium carbonate (0.16 g, 1.5 mmol), PdCl2(dppf) (0.03 g, 0.04 mmol), 1,2-dimethoxyethane (8 mL) and water (2 mL) and the mixture was refluxed for 2 h under nitrogen atmosphere. The mixture was evaporated under reduced pressure and purified by silica gel column chromatography using chloroform/methanol = 30: 1 as the eluent to afford the compounds T1-T6, T9-T10, T12 and T14-T21 as an off-white or a white solid.
4‑methoxy‑N’‑(1‑phenylethylidene)benzenesulfonohydrazide[ No CAS ]
[ 46407-51-6 ]
[ 1137-77-5 ]
Yield
Reaction Conditions
Operation in experiment
1: 83%
2: 7%
With di-tert-butyl(methyl)phosphonium tetrafluoroborate salt; palladium diacetate; potassium carbonate In N,N-dimethyl acetamide at 110℃; Inert atmosphere;
With Imidazole hydrochloride at 150℃; for 5h; Sealed tube;
3.2. General Procedures for the Synthesis of N-Acetamides 1a-1w
General procedure: To a mixture of aromatic or aliphatic or heterocyclic amine (3.0 mmol, 1.0 equiv.), Imidazolium chloride (1.0 mmol, 0.3 equiv.), N,N-Dimethyl acetamide (2.0 mL) was added. The mixture was refluxed at 150 °C and the progress of the reaction was monitored by TLC visualized with UV short wavelength followed by iodine stain. After completion, the mixture was diluted with cold water(10 mL) then extracted with EtOAc (10 mL). The EtOAc layer was washed with 1 M hydrochloric acid (3.0 15 mL). Adsorption of pigment with activated carbon, filtration of filtrate. The filtrate was dried over anhydrous Na2SO4 and concentrated under vacuum to obtain crude N-acetamide amine, the N-acetamide amine product was isolated by column chromatography eluting with petroleum ether:ethyl acetate (10:1) mixtures.
85%
With 1,2,4-Triazole; 8-quinolinol; copper(II) choride dihydrate at 150℃;
Stage #1: 4-bromoacetanilide With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 0.166667h;
Stage #2: With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 0.5h;
Stage #3: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -20℃; for 0.5h;
N-(4-Formyl-phenyl)-acetamide (3i)
To a solution of 4-Bromo-phen N-(4-Formyl -phenyl)-acetamide(1.5 g, 7.0 mmol, 1.0 equiv.) in dry THF (25 mL) at 0 C was added a 2 M solution of iPrMgCl in THF(3.5 mL, 7.0 mmol, 1.0 equiv.) during 5 min. The clear solution was stirred at that temperature for anadditional 5 min, and a 2.5 M solution of n-BuLi in hexanes (5.6 mL, 14.0 mmol, 2.0 equiv.) was addeddropwise during 5 min, while maintaining the temperature below 20 C. The resulting mixture wasstirred at that temperature for 0.5 h, dry DMF (0.5 g, 1.0 equiv.) in dry THF (5 mL) was added dropwiseduring 10 min. The resulting mixture was warmed to 20 C in 0.5 h and quenched with water (6 mL).After stirring the mixture below 20 C for 10 min, the phases were separated and the water phasewas extracted one additional time with ethyl acetate. The resulting suspension was allowed to reachroom temperature and fitered through a 0.5 1 cm pad of silica gel eluted with 10 mL of ethyl acetate.The filtrate was concentrated and the residue was purified by flash chromatography on silica gel(eluent: petroleum ether/ethyl acetate = 10:1) to afford product 3i as white solid, 1.0 g (yield: 94%) ,m.p.: 157-158 C. 1H-NMR (600 MHz, DMSO) 10.35 (s, 1H), 9.86 (s, 1H), 7.81 (dd, J = 32.9, 8.6 Hz,4H), 2.10 (s, 3H). 13C-NMR (151 MHz, DMSO) 191.92, 169.55, 145.29, 131.56, 131.27, 119.01, 24.68.
Under a nitrogen atmosphere, cuprous iodide (3.0 mol%, 0.7 mg), sodium iodide (1.0 equiv., 18.7 mg) and magnets were added to a previously baked 10 mL glass pressure tube. Dioxane (0.2 mL), 4-bromoacetanilide (0.125 mmol, 1.0 equiv., 26.8 mg) and N,N'-dimethylethylenediamine (10.0 mol%, 1.1 mg) were then added. After the addition was completed, the glass pressure tube was placed in a metal module that had been preheated to 100C and stirred for 10 hours. After cooling to room temperature, cuprous oxide (20 mol%, 3.6 mg), ferrous chloride (3 mol%, 0.5 mg), N-methylpyrrolidone (0.5 mL) and phenylsilane (3.0 equiv., 40.6) were added under nitrogen atmosphere. Mg). The tube was purged of air and charged with carbon dioxide (5.0 equiv., 15 mL) and ammonia gas (5.0 equiv., 15 mL). After the addition was completed, the reactor was placed in a metal module preheated to 160C and stirred for 10 hours. After the reaction was completed, the reaction system was cooled to room temperature and pressure was slowly released. Using dodecane as an internal standard, the yield was determined to be 91% by the gas chromatographic working curve.
3 mol of DL-methionine was added to 5 mol of 4-bromoacetanilide and dissolved by heating, and 5 mol of bromoethylamine was added. After refluxing for 120 min, 300 ml of a 35% ethanol solution was added, and the mixture was evaporated to dryness.The temperature of the residue was lowered to 15 C, washed with a mass fraction of 80% toluene solution, washed with a mass fraction of 90% nitroethane solution, recrystallized in a mass fraction of 96% butanol solution, and dehydrated to obtain a finished product. N-acetyl-DL-methionine 538.62 g, yield 94%.
N-(4-(2-cyclopropylethynyl)phenyl)acetamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
91%
Stage #1: 4-bromoacetanilide With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine; cesium fluoride In water at 20℃; for 0.25h; Sealed tube; Inert atmosphere;
Stage #2: (2-cyclopropylethynyl)trimethylsilane In water at 80℃; for 16h; Sealed tube; Inert atmosphere;
With hydrogen fluoride; In ethyl acetate; for 8.5h;Cooling with ice; Industrial scale;
Take 152kg of <strong>[6214-44-4]4-ethoxybenzyl alcohol</strong>, dissolve it in 300kg of ethyl acetate, add 212kg of 4-bromoacetanilide, add 40kg of HF in batches under ice bath, add in 60min, continue the reaction in ice bath for 30min, then heat the system. After refluxing for 7h, after the reaction is completed, it is cooled to room temperature, and the pH of the system is adjusted to 8-9 by 1mol/L sodium hydroxide solution. The organic layer is washed with saturated brine, washed with water until neutral, dried with anhydrous sodium sulfate, filtered, and the filtrate is reduced. The solvent was recovered by pressure, and 70% ethanol was crystallized to obtain 315 kg of yellow crystals, yield 91%.
Stage #1: 1-bromo-4-ethylbenzene With N-hydroxyphthalimide; oxygen; cobalt(II) diacetate tetrahydrate In acetic acid at 80℃; for 12h;
Stage #2: With formic acid; nitromethane; trifluoromethylsulfonic anhydride In acetic acid at 100℃; for 12h;
With morpholine; nickel(II) chloride ethylene glycol dimethyl ether complex; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-κN1,κN1′]bis[3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC]iridium hexafluorophosphate; 4,4’-di-tert-butyl-2,2’-bipyridine In N,N-dimethyl-formamide at 20℃; for 2h; Irradiation;
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