* 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] Roczniki Chemii, 1957, vol. 31, p. 1147,1151[2] Chem.Abstr., 1958, p. 10072
2
[ 3512-80-9 ]
[ 54221-93-1 ]
Reference：
[1] Roczniki Chemii, 1959, vol. 33, p. 387,392[2] Chem.Abstr., 1959, p. 18954
3
[ 3512-80-9 ]
[ 3512-75-2 ]
Reference：
[1] Chemische Berichte, 1894, vol. 27, p. 1323
[2] Roczniki Chemii, 1959, vol. 33, p. 387,392[3] Chem.Abstr., 1959, p. 18954
4
[ 3512-80-9 ]
[ 7647-01-0 ]
[ 7782-77-6 ]
[ 3512-75-2 ]
Reference：
[1] Chemische Berichte, 1894, vol. 27, p. 1323
5
[ 3512-80-9 ]
[ 5093-70-9 ]
Reference：
[1] Roczniki Chemii, 1959, vol. 33, p. 387,392[2] Chem.Abstr., 1959, p. 18954
[3] Patent: WO2006/89054, 2006, A1, . Location in patent: Page/Page column 59; 60-61
[4] Patent: WO2005/19228, 2005, A1, . Location in patent: Page/Page column 62-63
6
[ 4808-64-4 ]
[ 3512-80-9 ]
Yield
Reaction Conditions
Operation in experiment
71%
at 80℃; for 1 h;
A solution OF 4-NITRO-2, 6-DIMETHYLPYRIDINE-N-OXIDE (11.0 g, 65.4 mmol) in 50 mL of acetic acid was treated with iron powder (21.8 g, 390 mmol) in small portions while the mixture was rapidly stirred and gradually heated to 50 C (caution: the reaction becomes very exothermic at this temperature). After the exotherm ceased, the mixture was heated for an additional hour at 80 C. The resulting solidified mixture was treated with 50 ML of water and the suspension was filtered through CELITE filter aid. The filtrate was treated with ca. 200 ML of 6 N sodium hydroxide solution until the pH of the solution was basic (>12). The resulting green suspension was extracted with three 300 mL portions of chloroform. The extracts were combined, dried over magnesium sulfate, filtered, and concentrated in vacuo to give yellowish crystals (5.70 g, 71percent yield). A solution of 2, 6-dimethylpyridin-4-ylamine (2.00 g, 16. 4 MMOL) in 5 mL of acetic acid was treated dropwise with a solution of bromine (0.84 mL, 16.3 mmol) in 2 N-LL of acetic acid at room temperature in a water bath over a period of 10 minutes. After 1 hour, the resulting slurry was treated with 40 mL of 20percent sodium hydroxide solution and extracted with three 100 ML portions of dichloromethane (CH2CL2). The combined extracts were dried over magnesium sulfate, filtered, and concentrated IT7 VACUO. The resulting solid (starting material-desired PRODUCT-DIBROMO BYPRODUCT (1: 3: 1) ) was dissolved in 100 ML OF HOT HEXANES AND HOT FILTERED TO remove the insoluble starting material. The filtrate was allowed to cool to room temperature, which gave the title product as fine white needles (1. 30 g, 40percent yield).
35 g
With palladium 10% on activated carbon; acetic acid In water at 100℃; for 10 h; Autoclave
A 2L autoclave was charged with 60.0 g of 2,6-dimethyl-4-nitropyridine nitrogen oxide, 12.0 g of 10percent Pd/C catalyst, 1200 g of glacial acetic acid as a solvent, and hydrogenation at 100°C for 10 hours. The reaction pressure was: At 3 to 4 Pa, after completion of the reaction, the reaction mixture was concentrated under reduced pressure to remove acetic acid and water, and the product was recrystallized from acetone to obtain 35 g of an off-white powder.
Reference：
[1] Journal of Heterocyclic Chemistry, 1997, vol. 34, # 3, p. 717 - 727
[2] Patent: WO2005/30213, 2005, A1, . Location in patent: Page/Page column 166-167
[3] Organometallics, 2014, vol. 33, # 24, p. 7209 - 7214
[4] Acta Poloniae Pharmaceutica, 1955, vol. 12, p. 105,109[5] Chem.Abstr., 1956, p. 3427
[6] Yakugaku Zasshi, 1951, vol. 71, p. 156,159[7] Chem.Abstr., 1951, p. 9542
[8] Pharmaceutical Bulletin, 1954, vol. 2, p. 131,136
[9] Pharmaceutical Bulletin, 1956, vol. 4, p. 174,177
[10] Journal fuer Praktische Chemie (Leipzig), 1988, vol. 330, # 1, p. 154 - 158
[11] Patent: WO2005/30209, 2005, A1, . Location in patent: Page/Page column 51
[12] Patent: WO2006/89054, 2006, A1, . Location in patent: Page/Page column 59; 60
[13] Patent: WO2005/19228, 2005, A1, . Location in patent: Page/Page column 62-63
[14] Patent: CN107721915, 2018, A, . Location in patent: Paragraph 0025
[15] Patent: WO2004/26836, 2004, A2, . Location in patent: Page 30
7
[ 108-48-5 ]
[ 3512-80-9 ]
Reference：
[1] Journal of Heterocyclic Chemistry, 1997, vol. 34, # 3, p. 717 - 727
[2] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1915, vol. 47, p. 836[3] Chem. Zentralbl., 1916, vol. 87, # I, p. 1032
[4] Patent: CN107721915, 2018, A,
[5] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 25, p. 357
8
[ 1073-23-0 ]
[ 3512-80-9 ]
Reference：
[1] Journal of Heterocyclic Chemistry, 1997, vol. 34, # 3, p. 717 - 727
[2] Patent: CN107721915, 2018, A,
9
[ 3512-75-2 ]
[ 3512-80-9 ]
Reference：
[1] Journal of the Chemical Society, 1949, p. 1803,1806
10
[ 108-48-5 ]
[ 108-88-3 ]
[ 3512-80-9 ]
Reference：
[1] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1915, vol. 47, p. 836[2] Chem. Zentralbl., 1916, vol. 87, # I, p. 1032
11
[ 10034-85-2 ]
[ 3512-80-9 ]
[ 62-53-3 ]
Reference：
[1] Chemische Berichte, 1903, vol. 36, p. 1114
12
[ 3512-80-9 ]
[ 33259-24-4 ]
Yield
Reaction Conditions
Operation in experiment
40%
With bromine In acetic acid at 20℃; for 1.16667 h;
A solution OF 4-NITRO-2, 6-DIMETHYLPYRIDINE-N-OXIDE (11.0 g, 65.4 mmol) in 50 mL of acetic acid was treated with iron powder (21.8 g, 390 mmol) in small portions while the mixture was rapidly stirred and gradually heated to 50 C (caution: the reaction becomes very exothermic at this temperature). After the exotherm ceased, the mixture was heated for an additional hour at 80 C. The resulting solidified mixture was treated with 50 ML of water and the suspension was filtered through CELITE filter aid. The filtrate was treated with ca. 200 ML of 6 N sodium hydroxide solution until the pH of the solution was basic (>12). The resulting green suspension was extracted with three 300 mL portions of chloroform. The extracts were combined, dried over magnesium sulfate, filtered, and concentrated in vacuo to give yellowish crystals (5.70 g, 71percent yield). A solution of 2, 6-dimethylpyridin-4-ylamine (2.00 g, 16. 4 MMOL) in 5 mL of acetic acid was treated dropwise with a solution of bromine (0.84 mL, 16.3 mmol) in 2 N-LL of acetic acid at room temperature in a water bath over a period of 10 minutes. After 1 hour, the resulting slurry was treated with 40 mL of 20percent sodium hydroxide solution and extracted with three 100 ML portions of dichloromethane (CH2CL2). The combined extracts were dried over magnesium sulfate, filtered, and concentrated IT7 VACUO. The resulting solid (starting material-desired PRODUCT-DIBROMO BYPRODUCT (1: 3: 1) ) was dissolved in 100 ML OF HOT HEXANES AND HOT FILTERED TO remove the insoluble starting material. The filtrate was allowed to cool to room temperature, which gave the title product as fine white needles (1. 30 g, 40percent yield).
Bromine (4 g) is added, with stirring over 10 minutes, to a mixture of 4-amino-2, 6-lutidine (22, 1 g, approximately 6.5 mmol) in 48% HBr (12 ml) at -10 C, followed by cooling to -20 C. A solution of sodium nitrite (1.4 g) in water (4 ml) is added slowly. The mixture is EPO <DP n="62"/>stirred at -20 C for 1 hour, and then warmed and left at room temperature for 3 hours. The mixture is distilled. The oil fraction of the distillate is extracted with chloroform (3xlthetaml). The combined extracts are dried over magnesium sulfate. After filtration, the filtrate is neutralized in an ice-bath using 2M butyl lithium in hexanes until the pH reaches 7. A large amount of salt forms. After filtration, the filtrate is concentrated and dried, yielding 4-bromo-2,6-lutidine (23) oil. 1H NMR (300 MHz, CDCl3) delta 2.82 (s, 6H), 7.5 (s, 2H). MS, m/z 186 and 188 (M+l).
Bromine (4 g) is added, with stirring over 10 minutes, to a mixture of 4-amino- 2, 6-lutidine (22, 1 g, approximately 6. 5 mmol) in 48% HBr (12 ml) AT-10 C, followed by cooling to-20 C. A solution of sodium nitrite (1. 4 g) in water (4 ml) is added slowly. The mixture is stirred at-20 C for 1 hour, and then warmed and left at room temperature for 3 hours. The mixture is distilled. The oil fraction of the distillate is extracted with chloroform (3XLOML). The combined extracts are dried over magnesium sulfate. After filtration, the filtrate is neutralized in an ice-bath using 2M butyl lithium in hexanes until the pH reaches 7. A large amount of salt forms. After filtration, the filtrate is concentrated and dried, yielding 4-bromo-2, 6-lutidine (23) OIL. 1H NMR (300 MHz, CDCl3) 6 2. 82 (s, 6H), 7. 5 (s, 2H). MS, m/z 186 and 188 (M+1).
With bromine; In water; at -15℃;
4-Amino-2,6-dimethylpyridine first formed a salt with an acid, cooled to -15 ° C, and added liquid bromine.After the dropwise addition, the aqueous solution of sodium nitrite is added dropwise, and the pH of the solution is adjusted to be alkaline after the addition is completed.Further extraction, drying and concentration afforded 2,6-dimethyl-4-bromopyridine.
A mixture of 2,6-dimethylpyridin-4-amine (0.5 g, 4.07 mmol) and bromine (0.21 mL, 4.07 mmol) in acetic acid (1 mL) was stirred at room temperature for 2 h. The mixture was treated with aqueous 20% sodium hydroxide (10 mL) and extracted with 30 mL CH2C12. The combined organics were washed with brine, dried over Na2S04 and concentrated. The residue was suspended in hot heptanes. The solid material was collected and dried to yield 3-bromo-2,6- dimethylpyridin-4-amine (0.43 g, 52%). MS m/z 201.1, 203.1 [M+H]+.
40%
With bromine; In acetic acid; at 20℃; for 1.16667h;
A solution OF 4-NITRO-2, 6-DIMETHYLPYRIDINE-N-OXIDE (11.0 g, 65.4 mmol) in 50 mL of acetic acid was treated with iron powder (21.8 g, 390 mmol) in small portions while the mixture was rapidly stirred and gradually heated to 50 C (caution: the reaction becomes very exothermic at this temperature). After the exotherm ceased, the mixture was heated for an additional hour at 80 C. The resulting solidified mixture was treated with 50 ML of water and the suspension was filtered through CELITE filter aid. The filtrate was treated with ca. 200 ML of 6 N sodium hydroxide solution until the pH of the solution was basic (>12). The resulting green suspension was extracted with three 300 mL portions of chloroform. The extracts were combined, dried over magnesium sulfate, filtered, and concentrated in vacuo to give yellowish crystals (5.70 g, 71% yield). A solution of 2, 6-dimethylpyridin-4-ylamine (2.00 g, 16. 4 MMOL) in 5 mL of acetic acid was treated dropwise with a solution of bromine (0.84 mL, 16.3 mmol) in 2 N-LL of acetic acid at room temperature in a water bath over a period of 10 minutes. After 1 hour, the resulting slurry was treated with 40 mL of 20% sodium hydroxide solution and extracted with three 100 ML portions of dichloromethane (CH2CL2). The combined extracts were dried over magnesium sulfate, filtered, and concentrated IT7 VACUO. The resulting solid (starting material-desired PRODUCT-DIBROMO BYPRODUCT (1: 3: 1) ) was dissolved in 100 ML OF HOT HEXANES AND HOT FILTERED TO remove the insoluble starting material. The filtrate was allowed to cool to room temperature, which gave the title product as fine white needles (1. 30 g, 40% yield).
(2,6-dimethyl-pyridin-4-yl)-carbamic acid pentafluorophenyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
In tetrahydrofuran; at -10 - 20℃; for 48h;
A solution of 2, 6-dimethyl-pyridin-4-ylamine (Example C1. 2., 1.23 g, 10 MMOL) in THF (30 mL) is slowly added to a cooled (-10C) SOLUTION of bis (pentafluorophenyl) carbonate (3.94 g, 10 MMOL) in THF (10 mL). The mixture is stirred at r. t. for 48 h and the solution of title compound is used as stock solution for subsequent coupling reactions.
5-bromo-thiophene-2-sulfonic acid (2,6-dimethyl-pyridin-4-ylmethyl)-amide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
52%
With triethylamine; In tetrahydrofuran; at 0 - 20℃; for 16h;
To a stirred solution of commercially available 4-aminomethyl-2,6-dimethyl-pyridine [CAS-No. 324571-98-4 (0.24 g, 1.76 mmol) in THF (8 ml) was added at 0 C. (ice water bath) commercially available 5-bromo-thiophene-2-sulfonyl chloride (0.46 g, 1.76 mmol) dissolved in THF (8 ml) and triethylamine (0.27 ml, 1.94 mmol). The reaction mixture was stirred at room temperature for 16 h and evaporated. The crude product was further purified by flash chromatography (ethyl acetate/heptane) and crystallization from dichloromethane/hexane to yield the title compound (0.33 g, 52%) as a light red solid. MS (ISN) 359.0 [(M-H)-], mp 138 C.
With palladium on activated charcoal; hydrogen; In methanol;
<strong>[4913-57-9]4-nitro-2,6-dimethylpyridine</strong> at a Pd / C catalyst, methanol as the solvent, hydrogenation, filtration,The filtrate was concentrated to give 4-amino-2,6-dimethylpyridine;
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