* 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.
With potassium carbonate In 1,2-dimethoxyethane; water at 80℃;
REFERENCE EXAMPLE 31; 2-(3-Aminophenyl)pyridine; To a suspension of 2-bromopyridine (0.5 g, 3.2 mmol), 3-aminophenylboronic acid (0.49 g, 3.2 mmol), anhydrous K2CO3 (0.87 g, 6.3 mmol) and Pd(PPh3J4 (0.36 g, 0.32 mmol) in 1 ,2-dimethoxyethane (50 mL) under argon, water (0.66 mL) was added. The mixture was heated under argon at 80 °C overnight. It was allowed to cool and water and EtOAc were added. The phases were separated and the aqueous phase was reextracted with EtOAc. The combined organic phases were dried over Na2SO4 and the solvent was evaporated. The crude product obtained was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 0.22 g of the title compound (yield: 42percent). LC-MS (method 1): tR = 1.46 min; m/z = 171.2 [M+H]+.
Reference：
[1] Molecular Crystals and Liquid Crystals, 2006, vol. 458, # 1, p. 227 - 235
[2] Journal of Medicinal Chemistry, 2000, vol. 43, # 6, p. 1123 - 1134
[3] Patent: WO2007/339, 2007, A1, . Location in patent: Page/Page column 52
[4] Tetrahedron, 2006, vol. 62, # 49, p. 11483 - 11498
[5] Patent: US2006/94644, 2006, A1, . Location in patent: Page/Page column 23
[6] Patent: WO2007/130743, 2007, A2, . Location in patent: Page/Page column 64
[7] Patent: WO2005/40152, 2005, A1, . Location in patent: Page/Page column 56
[8] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 23, p. 7268 - 7271
2
[ 4253-79-6 ]
[ 15889-32-4 ]
Reference：
[1] Journal of the American Chemical Society, 2016, vol. 138, # 27, p. 8470 - 8475
[2] Patent: US5902813, 1999, A,
[3] Journal of Medicinal Chemistry, 2012, vol. 55, # 14, p. 6375 - 6380
[4] Journal of the Chemical Society, 1940, p. 1279,1283
[5] Canadian Journal of Chemistry, 1953, vol. 31, p. 457,466
[6] ChemPlusChem, 2015, vol. 80, # 6, p. 938 - 943
[7] Journal of Medicinal Chemistry, 2017, vol. 60, # 17, p. 7410 - 7424
3
[ 109-09-1 ]
[ 13331-27-6 ]
[ 15889-32-4 ]
Yield
Reaction Conditions
Operation in experiment
78%
With potassium carbonate; hydrazine hydrate In water; N,N-dimethyl-formamide at 80℃; for 9 h;
General procedure: Aryl halide (1.0 mmol), phenylboronic acid (1.1 mmol),K2CO3(2.0 mmol), Ni7–Pd3BIHPS (0.03 g) and H2O/DMF (2:1, 3 mL) were mixed and heated at 80 °C for anappropriate time (monitored by TLC). Then, hydrazinehydrate (80 wtpercent, 6 eq) was added to the reaction vessel.After completion of the reduction process, the mixturewas filtered and washed with water. The organic layer wasextracted with ethyl acetate (3 × 15 mL) and dried overMgSO4.Then the organic solution was concentrated andpurified by column chromatography to obtain the finalproduct.
With tetrakis(triphenylphosphine) palladium(0) In toluene for 12 h; Reflux
To a 500 ml round bottom flask was added 20.0 g (116 mmol) of 3-bromoaniline,85.6 g (233 mmol) of 2- (tributylstannyl) pyridine,1.34 g (116 mmol) of tetrakistriphenylphosphine palladium,200 ml of toluene was added and the mixture was refluxed for 12 hours.After completion of the reaction, the temperature was cooled down to room temperature.The organic layer was extracted with ethyl acetate and water and concentrated under reduced pressure.Column purification was carried out using ethyl acetate and n-hexane as eluent. (12.7 g, yield 64percent).
With sodium carbonate In 1,2-dimethoxyethane; water for 5 h; Reflux
(i) 3-(Pyridin-2-yl)aniline 3.72 g (20.0 mmol) of 3-aminophenyl boronic acid* hemisulphate salt, 3.16 g (20.0 mmol) of 2-bromopyridine, 1.16 g (1.0 mmol) of tetrakis(triphenyl phosphine)palladium(0), and 11.2 g (106 mmol) of sodium carbonate were heated under reflux for 5 hours in a mixed solvent of 100 mL of DME and 34 mL of water. After completion of the reaction, extraction with ethyl acetate, and drying over anhydrous sodium sulfate were carried out. The solvent was distilled off under reduced pressure. The resulting crude product was separated and purified using silica gel column chromatography to give 1.27 g of 3-(pyridin-2-yl)aniline (yield: 37percent). 1H-NMR (CDCl3) δ: 3.76 (2H, br), 6.65-6.78 (1H, m), 7.10-7.40 (4H, m), 7.60-7.78 (2H, m), 8.60-8.70 (1H, m).
Reference：
[1] Journal of the American Chemical Society, 2016, vol. 138, # 27, p. 8470 - 8475
[2] Journal of the American Chemical Society, 2016, vol. 138, # 27, p. 8470 - 8475
[3] Journal of the American Chemical Society, 2016, vol. 138, # 27, p. 8470 - 8475
11
[ 109-04-6 ]
[ 15889-32-4 ]
Reference：
[1] Journal of Medicinal Chemistry, 2017, vol. 60, # 17, p. 7410 - 7424
12
[ 13331-27-6 ]
[ 15889-32-4 ]
Reference：
[1] Journal of Medicinal Chemistry, 2017, vol. 60, # 17, p. 7410 - 7424
palladium; In ethanol; ethyl acetate; Petroleum ether;
EXAMPLE 5 3-(2-Pyridyl)aniline (2f): To a solution of 2-(3-nitrophenyl)pyridine (prepared as described in J. Chem. Soc. 1958 p. 1759) (12.7g, 63.5mmol) in abs. ethanol is added palladium catalyst (1.3g 5% Pd on activated carbon) and the mixture is hydrogenated at ambient pressure until the hydrogen uptake has ceased. The mixture is filtered through celite and the filtrate is concentrated under reduced pressure. The residue is purified by column-chromatography on silica gel using a mixture of ethyl acetate and petroleum ether (9:1)as the eluent to afford 2f (9.5g, 88%) as a light brown oil.
(b) In a manner similar to that of Example 7(b), the above nitro compound (0.92 g) gives 2-(3-aminophenyl)pyridine (0.50 g) as a colourless oil.
6
[ 109-04-6 ]
[ 30418-59-8 ]
[ 15889-32-4 ]
Yield
Reaction Conditions
Operation in experiment
42%
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 80℃;
REFERENCE EXAMPLE 31; 2-(3-Aminophenyl)pyridine; To a suspension of 2-bromopyridine (0.5 g, 3.2 mmol), 3-aminophenylboronic acid (0.49 g, 3.2 mmol), anhydrous K2CO3 (0.87 g, 6.3 mmol) and Pd(PPh3J4 (0.36 g, 0.32 mmol) in 1 ,2-dimethoxyethane (50 mL) under argon, water (0.66 mL) was added. The mixture was heated under argon at 80 C overnight. It was allowed to cool and water and EtOAc were added. The phases were separated and the aqueous phase was reextracted with EtOAc. The combined organic phases were dried over Na2SO4 and the solvent was evaporated. The crude product obtained was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 0.22 g of the title compound (yield: 42%). LC-MS (method 1): tR = 1.46 min; m/z = 171.2 [M+H]+.
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 90℃;
Step A: 2-Bromopyridine (2.00 mL), 3-aminophenylboronic acid (5.40 g) and palladium tetrakistriphenylphosphine (1.2512 g) were added to a mixture of 130 mL of dimethoxyethane and 32 mL of 2.0 M aqueous potassium carbonate under an atmosphere of dry N2. The reaction mixture was heated at 90 C. overnight. The reaction mixture was then cooled to room temperature and diluted with water (300 mL). The resulting precipitate was collected, washed with water and air-dried. The dried material was purified using silica gel chromatography to give 2.75 g of 3-(pyridin-2-yl)benzenamine.
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 90℃;
2-Bromopyridine (2.00 mL), 3-aminophenylboronic acid (5.40 g) and palladium tetrakistriphenylphosphine (1.2512 g) were added to a mixture of 130 mL of dimethoxyethane and 32 mL of 2.0 M aqueous potassium carbonate under an atmosphere of dry N2. The reaction mixture was heated at 90 C overnight. The reaction mixture was then cooled to room temperature and diluted with water (300 mL). The resulting precipitate was collected, washed with water and air-dried. The dried material was purified using silica gel chromatography to give 2.75 g of 3-(pyridin-2-yl)benzenamine.
Step F: Preparation of 3-(2-pyridinyl)benzenamine; To a solution of 2-bromopyridine (1.6 g, 10 mmol) in dimethoxyethane (50 mL) and water (17 mL) was added 3-aminophenylboronic acid hemisulfate (1.86 g, 10 mmol), sodium carbonate (5.6 g, 52.8 mmol) and tetrakis (triphenylphosphine) palladium (0) (0.3 g). The mixture was heated to reflux for 5 hours and then allowed to cooled to room temperature. Brine (50 mL) was added, and the mixture was extracted with ethyl acetate (3 x 25 mL). The organic extracts were dried (MgS04) and concentrated to leave the crude product. The crude product was purified by flash column chromatography to provide the title compound as a thick yellow oil (1.1 g). 11-1 NMR (CDC13) 8 8.6 (m, 1H), 7.69 (m, 2H), 7. 3 (m, 4H), 6.8 (m, 1H), 3.8 (br s 2H).
With palladium diacetate; potassium carbonate; triphenylphosphine; In ethanol; toluene; at 60℃; for 12h;Inert atmosphere;
General procedure: The general procedure for the preparation of N-(3-phenyl)-2,2-dichloroacetamide heterocyclic derivatives was as follows. A mixture of 1 mmol aryl(heterocyclic) bromide, 1.5 mmol 3-aminophenylboronic acid, 2 mmol K2CO3, Triphenyl phosphine at 0.4 mmol and palladium acetate at 0.1 mmol were stirred in 6 mL toluene and 6 mL ethanol at 60? under an argon atmosphere. The progress of the reaction was monitored by TLC (petroleum ether/ethyl acetate). After the reaction finished, the reaction mixture was filtered. The filtrate was concentrated to dryness and subjected to flash column chromatography (silica gel), eluting with petroleum ether/ethyl acetate, to give 3-aryl (hetero) aniline.
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,2-dimethoxyethane; water; at 80℃;Inert atmosphere;
To a suspension of 2-bromopyridine (0.5 g, 3.2 mmol), 3-aminophenylboronic acid (0.49 g, 3.2 mmol), anhydrous K2CO3 (0.87 g, 6.3 mmol) and Pd(PPh3)4 (0.36 g, 0.32 mmol) in 1,2-dimethoxyethane (50 mL) under argon, water (0.66 mL) is added. The mixture is heated under argon at 80 C. overnight. The reaction mixture is allowed to cool and water and EtOAc is added. The phases are separated in a funnel and the aqueous phase is reextracted with EtOAc. The combined organic phases are dried over Na2SO4 and the solvent Is evaporated. The crude product obtained is purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford the title compound.
3-(1,1-dimethylethyl)-1-ethyl-N-[3-(2-pyridinyl)phenyl]-1H-pyrazole-5-carboxamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With triethylamine; In dichloromethane; at 0 - 20℃; for 1.01667h;
Step G: Preparation of 3-(1, 1-dimethylethyl)-1-ethyl-N-E3-(2-pyridinyl) phenyl]-lH- pyrazole-5-carboxamide; To a solution of 3- (2-pyridinyl) benzenamine (i. e. the product of Step F) (0.34 g, 2 mmol) in dichloromethane (5 mL), triethylamine (0.3 mL, 2. 2 mmol) was added, and the solution was cooled to 0 C. To this a solution of 3- (1, 1-dimethylethyl)-1-ethyl- 1H pyrazole-5-carbonyl chloride (i. e. the product of Step E) (0.43 g, 2 mmol) in dichloromethane (2 mL) was added over one minute, and then the mixture was allowed to come to room temperature while being stirred for one hour. The mixture was concentrated, and the residue was purified using a silica gel flash chromatography column eluted with hexane-ethyl acetate (8: 2 and then 1 : 1) to provide the titles compound, a compound of present invention, as a white solid (0.25 g). 1H NMR (CDC13) 8 8.7 (m, 1H), 8.2 (s, 1H), 7.8 (m, 1H), 7. 77 (m, 4H), 7.5 (m, 1H), 7.23 (m, 1H), 6.47 (s, 1H), 4.59 (q, 2H), 1.49 (t, 3H), 1.36 (s, 9H).
2-(1,1-dimethylethyl)-5-ethyl-N-[3-(2-pyridinyl)phenyl]-2H-1,2,3-triazole-4-carboxamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In dichloromethane; at 20℃; for 2h;
Step C: Preparation of 2- (1, 1-dimethylethyl)-5-ethyl-N [3- (2-pyridinyl) phenyl] - 2H-1, 2,3-triazole-4-carboxamide; To a stirred solution of ethyl 2- (1, 1-dimethylethyl)-5-ethyl-2H-1, 2,3-triazole- 4-carboxylate (i. e. the first eluted product of Step B) (1.119 g, 5.64 mmol) in tetrahydrofuran (15 mL) was added a solution of lithium hydroxide (0.54 g, 22.56 mmol) in water (15 mL). The mixture was stirred at room temperature overnight, and then partitioned between ether and water. The aqueous layer was acidified with hydrochloric acid (6 N) to pH 1-2 and extracted with ethyl acetate, dried (NaSOq,) and concentrated to provide the carboxylic acid intermediate as a white solid (0.94 g, 5. 08 mmol, 90% yield). To a solution of the carboxylic acid intermediate (0.1 g, 0.5 mmol) in dichloromethane (2 mL) at room temperature was added sequentially 1-propanephosphonic acid cyclic anhydride (50% in ethyl acetate, 0.25 g, 0.785 mmol), 3- (2-pyridinyl) benzenamine (i. e. the product of Example 1, Step F) (0. 1 g, 0. 58 mmol) and triethylamine (0.1 mL, 0.75 mmol). After stirring at room temperature 2 h the mixture was concentrated, and the residue was purified using silica gel column chromatography eluted with hexane-ethyl acetate (9: 1) to provide the title product, a compound of the present invention, as an off-white solid (0.07 g). 1H NMR (CDC13) 6 7.75 (m, 2H), 8.2 (m, 1H), 8.0 (d, 1H), 7.8 (m, 1H), 7.75 (m, 2H), 7.4 (t, 1H), 7.25 (m, 1H), 3.06 (m, 2H), 1.58 (s, 9H), 1.29 (t, 3H).
3-Cyclohexyl-6-(2-pyridyl)-1,2,3,4-tetrahydro-1,2,4-benzothiadiazine-1,1-dioxide 3-Aminophenylboronic acid hemisulphate (5.58 g, 30 mmol), 2-bromopyridine (2.7 ml, 28 mmol), Pd(PPh3)2Cl2 (100 mg, 0.5 mol %), 2M K2CO3 (50 ml) were refluxed in 1,2-dimethoxyethane (50 ml) for 24 h under N2. The mixture was diluted with CH2Cl2 (100 ml) and washed with sat. NaHCO3 (50 ml). The organic layer was dried (Na2SO4) and the solvent was removed under reduced pressure. Flash-chromatography with CH2Cl2 as eluent gave 3-(2-pyridyl)aniline as a yellow oil, 1.0 g (21%).
With sodium carbonate; In 1,2-dimethoxyethane; water; for 5h;Reflux;
(i) 3-(Pyridin-2-yl)aniline 3.72 g (20.0 mmol) of 3-aminophenyl boronic acid· hemisulphate salt, 3.16 g (20.0 mmol) of 2-bromopyridine, 1.16 g (1.0 mmol) of tetrakis(triphenyl phosphine)palladium(0), and 11.2 g (106 mmol) of sodium carbonate were heated under reflux for 5 hours in a mixed solvent of 100 mL of DME and 34 mL of water. After completion of the reaction, extraction with ethyl acetate, and drying over anhydrous sodium sulfate were carried out. The solvent was distilled off under reduced pressure. The resulting crude product was separated and purified using silica gel column chromatography to give 1.27 g of 3-(pyridin-2-yl)aniline (yield: 37%). 1H-NMR (CDCl3) delta: 3.76 (2H, br), 6.65-6.78 (1H, m), 7.10-7.40 (4H, m), 7.60-7.78 (2H, m), 8.60-8.70 (1H, m).
General procedure: A mixture of 3-aryl (hetero) aniline (1 mmol) and dichloroacetyl chloride (1.3 mmol, 1.3 equiv) were stirred in dry toluene (20 mL) at reflux. The progress of the reaction was monitored by TLC (petroleum ether/ethyl acetate). After 1-5 h, the solvent and excess dichloroacetyl chloride was evaporated under vacuum to give the residual powder as N-(3-aryl(hetero)-phenyl)-2,2-dichloroacetamide derivatives (90%-99% yield).
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; sodium t-butanolate; In toluene; for 24h;Inert atmosphere; Reflux;
10.5 g (34.1 mmol) of compound (IV) and 5.8 g (34.1 mmol) of compound (II) are suspended in 400 ml_ of toluene under Ar atmosphere. 380 mg (0.68 mmol) of 1 ,1-bis-(diphenylphosphino)-ferrocene and 150 mg (0.68 mmol) of Pd(OAc)2 are added to the flask and stirred vigorously under Ar atmostphere. Then 3.9 g (40.9 mmol) of sodium t-butoxide is added to the flask under Ar. The reaction mixture is stirred under reflux for 24 h. After cooling, the organic phase is separated off, washed three times with 100 mL of water, dried over magnesium sulfate, filtered and subsequently evaporated to dryness. The residue is purified by column chromatography on silica gel using a mixture of ethylacetate/heptane (1 :2) . The yield is 11.1 g (27.9 mmol), corresponding to 82% of theory.
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; sodium t-butanolate; In toluene; for 24h;Inert atmosphere; Reflux;
7.2 g (30.6 mmol) of compound (I) and 5.2 g (30.6 mmol) of compound (II) are suspended in 200 ml_ of toluene under Ar atmosphere. 340 mg (0.61 mmol) of 1 ,1-bis-(diphenylphosphino)-ferrocene and 140 mg (0.61 mmol) of Pd(OAc)2 are added to the flask and stirred vigorously under Ar atmosphere. Then 3.5 g (36.7 mmol) of sodium t-butoxide is added to the flask under Ar. The reaction mixture is stirred under reflux for 24 h. After cooling to room temperature, the organic phase is separated off, washed three times with 100 ml_ of water, dried over magnesium sulfate,filtered and subsequently evaporated to dryness. The residue is purified by column chromatography on silica gel using a mixture of ethylacetate/heptane (1 :2) . The yield is 8.2 g (29.4 mmol), corresponding to 96percent of theory.
72%
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; for 20h;Reflux;
5.0 g (64.1 mmol) of the compound represented by the formula (1-a) obtained from the above-mentioned scheme 1 and 10.9 g of the compound represented by the formula (1-b) obtained from the above scheme 2 were added to a 500 ml round bottom flask 64.1 mmol), Pd2 (dba) 3 (1.17 g, 1.28 mmol),0.260 g (1.28 mmol) of tri (tertiary butyl) phosphine, 12.3 g (128 mmol) of sodium tertiary butoxide and 200 ml of toluene were placed and refluxed for 20 hours.After completion of the reaction, the temperature was lowered to room temperature and filtered.The organic layer was concentrated under reduced pressure, and then subjected to column purification using 14.9 g (yield: 72.0percent) of ethyl acetate and n-hexane as eluent.
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl acetamide; at 20℃;
General procedure: A mixture of the carboxylic acid 6a (0.5 g, 1.66 mmol), amine (8a) (0.193 g, 1.74 mmol), WSC HCl(0.382 g, 1.99 mmol), HOBt (0.269 g, 1.99 mmol) in DMA (5 mL) was stirred at room temperature. Aftercompletion of the reaction, the reaction mixture was poured into an aqueous NaHCO3 solution. The solidwas separated by filtration, and washed with water to afford the corresponding amide (12a) as a solid(0.281g, 82%).
With potassium carbonate; hydrazine hydrate; In water; N,N-dimethyl-formamide; at 80℃; for 9h;
General procedure: Aryl halide (1.0 mmol), phenylboronic acid (1.1 mmol),K2CO3(2.0 mmol), Ni7-Pd3BIHPS (0.03 g) and H2O/DMF (2:1, 3 mL) were mixed and heated at 80 C for anappropriate time (monitored by TLC). Then, hydrazinehydrate (80 wt%, 6 eq) was added to the reaction vessel.After completion of the reduction process, the mixturewas filtered and washed with water. The organic layer wasextracted with ethyl acetate (3 × 15 mL) and dried overMgSO4.Then the organic solution was concentrated andpurified by column chromatography to obtain the finalproduct.
With tetrakis(triphenylphosphine) palladium(0); In toluene; for 12h;Reflux;
To a 500 ml round bottom flask was added 20.0 g (116 mmol) of 3-bromoaniline,85.6 g (233 mmol) of 2- (tributylstannyl) pyridine,1.34 g (116 mmol) of tetrakistriphenylphosphine palladium,200 ml of toluene was added and the mixture was refluxed for 12 hours.After completion of the reaction, the temperature was cooled down to room temperature.The organic layer was extracted with ethyl acetate and water and concentrated under reduced pressure.Column purification was carried out using ethyl acetate and n-hexane as eluent. (12.7 g, yield 64%).
Preparation follows the literature procedure described in J. Org. Chem. 2016, 81, 3256-3262. Equal amounts of compound 1 and 2 are added to a microwave vial (10 ml) equipped with a magnetic stirrer followed by a small addition of EtOH/H2O. The reaction is performed in a closed vial for half hour. After completion of the reaction, the mixture is concentrated under vacuum. The residue is purified by chromatography on reverse phase.
With oxygen; copper(II) bis(trifluoromethanesulfonate); toluene-4-sulfonic acid; In ethanol; at 80℃; for 72h;
Weigh m-aminoacetophenone (100.0mg, 0.74mmol) in ethanol (3mL),Cu (OTf) 2 (26.8mg, 0.074mmol), TsOH · H2O (84.4mg, 0.44mmol), 1,3-propanediamine (185muL, 2.22mmol) were added in this order,Ventilation and oxygen, heating to 80 C for 72h.After the reaction was completed, the reaction solution was cooled to room temperature, and concentrated by rotary evaporation. Ethyl acetate, water, and saturated sodium carbonate were added to make the mixture alkaline.Extract with ethyl acetate (25 mL x 3), wash with saturated brine (30 mL x 2), and dry over anhydrous sodium sulfate.Column chromatography (EA: PE 1: 3) yielded 62.3 mg of the product with a yield of 49.5%.
2-chloro-4-methanesulfonyl-N-[3-(pyridin-2-yl)phenyl]benzamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Weigh 2-chloro-4-methylsulfonylbenzoic acid (165.5mg, 0.71mmol) and dissolve in DCM (10mL)Add 4 drops of DMF and heat to reflux. The solution gradually cleared and the endpoint of the reaction was monitored by TLC.After the reaction was completed, excess SOCl2 and DCM were removed by rotary evaporation and dissolved in anhydrous THF (10 mL).Take the 3- (2-pyridyl) aniline (100 mg, 0.59 mmol) prepared above and dissolve it in anhydrous THF (5 ml).TEA (164 muL, 1.18 mmol) was added and the ice-water bath was cooled to 0 C.The prepared anhydrous solution of 2-chloro-4-methylsulfonylbenzoyl chloride in THF was slowly added dropwise to the above solution,After the dropwise addition was completed, the temperature was slowly raised to room temperature for 5 hours, and the reaction endpoint was monitored by TLC. After the reaction was completed, the solution was in suspension.0.5 mL of distilled water was added and the solution gradually cleared. It was washed with saturated sodium carbonate solution (2 mL x 2) and the solution was separated.Take the organic phase slowly and add it to 50mL of distilled water. A white solid precipitates out and is filtered.Drying under vacuum gave 204.7 mg of a white solid with a yield of 90.1%.
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