* 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 iron; ammonium chloride In ethanol at 25 - 90℃; for 2 h;
IM01: 2-Methoxy-4-methyl-pyridin-3-ylamineThe title compound is commercially available. A mixture of 4-methyl-2-methoxy-3-nitropyridine (4.5 g, 26.8 mmol), NH4Cl (7.16 g, 133.9 mmol) and Fe powder (7.5 g, 133.9 mmol) in ethanol (50 mL) was stirred at 25° C. The mixture was slowly heated to 90° C. and stirred at this temperature for 2 h. The reaction mixture was filtered through a plug of celite and the celite plug was washed with ethanol (50 mL). The combined filtrates were evaporated to dryness. The remanens was diluted with water (50 mL) and the mixture was extracted with EtOAc (100 mL). The organic layer was dried over Na2SO4. Evaporation to dryness gave the title compound as a solid (3.5 g, 81percent). 1H NMR (CDCl3, 400 MHz) δ 7.50-7.49 (1H, d, J=5.2 Hz), 6.62-6.61 (1H, d, J=5.2 Hz), 3.97 (3H, s), 3.79-3.69 (2H, br s), 2.15 (3H, s).
81%
With ammonium chloride In ethanol at 25 - 90℃; for 2 h;
The title compound is commercially available. A mixture of 4-methyl-2-methoxy-3- nitropyridine (4.5 g, 26.8 mmol), NH4CI (7.16 g, 133.9 mmol) and Fe powder (7.5 g, 133.9 mmol) in ethanol (50 mL) was stirred at 25 °C. The mixture was slowly heated to 90 °C and stirred at this temperature for 2 h. The reaction mixture was filtered through a plug of celite and the celite plug was washed with ethanol (50 mL). The combined filtrates were evaporated to dryness. The remanens was diluted with water (50 mL) and the mixture was extracted with EtOAc (100 mL). The organic layer was dried over Na2S04. Evaporation to dryness gave the title compound as a solid (3.5 g, 81 percent). 1 H NMR (CDCI3, 400 MHz) δ 7.50-7.49 (1 H, d, J = 5.2 Hz), 6.62-6.61 (1 H, d, J = 5.2 Hz), 3.97 (3H, s), 3.79-3.69 (2H, br s), 2.15 (3H, s).
Reference：
[1] Patent: US2013/5743, 2013, A1, . Location in patent: Page/Page column 12
[2] Patent: WO2013/4617, 2013, A1, . Location in patent: Page/Page column 29
[3] Chemical and Pharmaceutical Bulletin, 2008, vol. 56, # 6, p. 775 - 780
2
[ 23056-39-5 ]
[ 124-41-4 ]
[ 160590-36-3 ]
Yield
Reaction Conditions
Operation in experiment
100%
at 0℃; for 25 h; Reflux
A solution of 2-chloro-4-methyl-3 -nitropyridine (250 g, 1.45 mol) in methanol (1.0 L) was added dropwise (2 h) to a stirred and cooled (0 °C) solution of sodium methoxide (250 g,4.63 mol) in methanol (850 mL). After addition, the mixture was heated to reflux for 23 h, at which time TLC indicated the reaction had gone to completion. The mixture was concentrated under reduced pressure to a volume of approximately 900 mL, and quenched by addition of water (1.5 L). The resulting solid was collected by filtration, washed with water and dried under reduced pressure to give the title compound (250 g, 100percent yield) as a brownsolid. ‘H NMR (400 MHz, DMSO-d6): 8.22 (d, J= 5.2 Hz, 1 H), 7.10 (d, J= 5.6 Hz, I H),3.92 (s, 3 H), 2.26 (s, 3 H).
100%
at 0℃; for 23 h; Reflux
A solution of 2-chloro-4-methyl-3 -nitropyridine (250 g, 1.45 mol) in methanol (1.0 L) was added dropwise (2 h) to a stirred and cooled (0 °C) solution of sodium methoxide (250 g, 4.63 mol) in methanol (850 mL). After addition, the mixture was heated to reflux for 23 h, at which time TLC indicated the reaction had gone to completion. The mixture was concentrated under reduced pressure to a volume of approximately 900 mL, and quenched by addition of water (1.5 L). The resulting solid was collected by filtration, washed with water and dried under reduced pressure to give the title compound (250 g, 100percent yield) as a brown solid. NMR (400 MHz, DMSO-<): δ 8.22 (d, J= 5.2 Hz, 1 H), 7.10 (d, J= 5.6 Hz, 1 H), 3.92 (s, 3 H), 2.26 (s, 3 H)
100%
at 0℃; for 23 h; Reflux
A solution of 2-chloro-4-methyl-3-nitropyridine (250 g, 1.45 mol) in methanol (1.0 L) was added dropwise (2 h) to a stirred and cooled (0 °C) solution of sodium methoxide (250 g, 4.63 mol) in methanol (850 mL). After addition, the mixture was heated to reflux for 23 h, at which time TLC indicated the reaction had gone to completion. The mixture was concentrated under reduced pressure to a volume of approximately 900 mL, and quenched by addition of water (1.5 L). The resulting solid was collected by filtration, washed with water and dried under reduced pressure to give the title compound (250 g, 100percent yield) as a brown solid. 1H NMR (400 MHz, DMSO-d6): δ 8.22 (d, J= 5.2 Hz, 1 H), 7.10 (d, J= 5.6 Hz, 1 H), 3.92 (s, 3 H), 2.26 (s, 3 H).
100%
at 0℃; for 23 h; Reflux
A solution of 2-chloro-4-methyl-3 -nitropyridine (250 g, 1.45 mol) in MeOH (1.0 L) was added dropwise over 2 h to a stirred and cooled (0 °C) solution of NaOMe (250 g, 4.63 mol) in MeOH (850 mL). The reaction was heated to reflux temperature for 23 h. The mixture was partially concentrated under reduced pressure and quenched by the addition of water (1.5 L), the resulting solid was collected by filtration, washed with water and dried under vacuum to give the titlecompound (250 g, 100percent yield) as a brown solid. ‘H NMR (400 MHz, DMSO-d6): ö 8.22 (d, J5.2 Hz, 1 H), 7.10 (d, J= 5.6 Hz, 1 H), 3.92 (s, 3 H), 2.26 (s, 3 H).
Reference：
[1] Patent: WO2016/77378, 2016, A1, . Location in patent: Page/Page column 85; 157; 158; 163; 164
[2] Patent: WO2016/77380, 2016, A1, . Location in patent: Page/Page column 63
[3] Patent: WO2016/77375, 2016, A1, . Location in patent: Page/Page column 79
[4] Patent: WO2016/123391, 2016, A1, . Location in patent: Page/Page column 76; 185; 186
[5] Journal of Organic Chemistry, 2001, vol. 66, # 17, p. 5723 - 5730
[6] Chemical and Pharmaceutical Bulletin, 2008, vol. 56, # 6, p. 775 - 780
3
[ 67-56-1 ]
[ 23056-39-5 ]
[ 124-41-4 ]
[ 160590-36-3 ]
Reference：
[1] Journal of Medicinal Chemistry, 2016, vol. 59, # 11, p. 5391 - 5402
4
[ 160590-36-3 ]
[ 160590-40-9 ]
Reference：
[1] Journal of Organic Chemistry, 2001, vol. 66, # 17, p. 5723 - 5730
[2] Patent: US2015/307465, 2015, A1,
5
[ 160590-36-3 ]
[ 884495-14-1 ]
Yield
Reaction Conditions
Operation in experiment
82.2%
at 80℃; for 12.5 h;
Sodium acetate (365 g, 5.37 mol) was added to a stirred solution of 2-methoxy-4-methyl-3-nitropyridine (250 g, 1.49 mol) in acetic acid (1 .5 L) at ambient temperature and then Br2(639 g, 4.00 mol) was added dropwise (30 mm). After addition, the mixture was heated at 80°C for 12 h, at which time TLC indicated the reaction had gone to completion. The mixturewas cooled (0 °C) and quenched by sequential addition of 10percent aqueous (1.5 L) and saturatedaqueous sodium sulfate (1.5 L). The resulting solid was collected by filtration, washed withwater, and dried under reduced pressure to give the title compound (302 g, 82.2percent yield) as alight yellow solid. h11 NMR (400 MHz, DMSO-d6): 6 8.25 (s, 1 H), 3.94 (s, 3 H), 2.29 (s, 3H).
82.2%
at 80℃; for 12 h;
Sodium acetate (365 g, 5.37 mol) was added to a stirred solution of 2-methoxy-4 -methyl -3- nitropyridine (250 g, 1.49 mol) in acetic acid (1.5 L) at ambient temperature and then Br2 (639 g, (0447) 4.00 mol) was added dropwise (30 min). After addition, the mixture was heated at 80 °C for 12 h, at which time TLC indicated the reaction had gone to completion. The mixture was cooled (0 (0448) °C) and quenched by sequential addition of 10percent aqueous (1.5 L) and saturated aqueous sodium sulfite (1.5 L). The resulting solid was collected by filtration washed with water, and dried under reduced pressure to give the title compound (302 g, 82.2percent yield) as a light yellow solid. (0449) NM (400 MHz, DMSO-iM): δ 8.25 (s, 1 H), 3.94 (s, 3 H), 2.29 (s, 3 H)
82.2%
at 20 - 80℃; for 12 h;
Sodium acetate (365 g, 5.37 mol) was added to a stirred solution of 2-methoxy-4-methyl-3- nitropyridine (250 g, 1.49 mol) in acetic acid (1.5 L) at ambient temperature and then Br2 (639 g, 4.00 mol) was added dropwise (30 min). After addition, the mixture was heated at 80 °C for 12 h, at which time TLC indicated the reaction had gone to completion. The mixture was cooled (0 °C) and quenched by sequential addition of 10percent aqueous (1.5 L) and saturated aqueous Na2S03 (1.5 L). The resulting solid was collected by filtration washed with water, and dried under reduced pressure to give the title compound (302 g, 82.2percent yield) as a light yellow solid. 1H NMR (400 MHz, DMSO-t 6): δ 8.25 (s, 1 H), 3.94 (s, 3 H), 2.29 (s, 3 H).
82.2%
at 20 - 80℃; for 12 h;
BrSodium acetate (365 g, 5.37 mol) was added to a stirred solution of 2-methoxy-4-methyl-3-nitropyridine (250 g, 1.49 mol) in acetic acid (1.5 L) at ambient temperature, then bromine (639g, 4.00 mol) was added and the reaction was heated at 80 °C for 12 h. The mixture was then quenched by the addition of 10percent aqueous NaOH (1.5 L) and saturated aqueous Na2SO3 (1.5 L) at 0 °C. The resulting solid was collected by filtration and washed with water, dried under vacuum to give the title compound (302 g, 82.2percent yield) as a light yellow solid. ‘H NMR (400MHz, DMSO-d6): ö 8.25 (s, 1 H), 3.94 (s, 3 H), 2.29 (s, 3 H).
With iron; ammonium chloride; In ethanol; at 25 - 90℃; for 2h;
IM01: 2-Methoxy-4-methyl-pyridin-3-ylamineThe title compound is commercially available. A mixture of 4-methyl-2-methoxy-3-nitropyridine (4.5 g, 26.8 mmol), NH4Cl (7.16 g, 133.9 mmol) and Fe powder (7.5 g, 133.9 mmol) in ethanol (50 mL) was stirred at 25 C. The mixture was slowly heated to 90 C. and stirred at this temperature for 2 h. The reaction mixture was filtered through a plug of celite and the celite plug was washed with ethanol (50 mL). The combined filtrates were evaporated to dryness. The remanens was diluted with water (50 mL) and the mixture was extracted with EtOAc (100 mL). The organic layer was dried over Na2SO4. Evaporation to dryness gave the title compound as a solid (3.5 g, 81%). 1H NMR (CDCl3, 400 MHz) delta 7.50-7.49 (1H, d, J=5.2 Hz), 6.62-6.61 (1H, d, J=5.2 Hz), 3.97 (3H, s), 3.79-3.69 (2H, br s), 2.15 (3H, s).
81%
With ammonium chloride; In ethanol; at 25 - 90℃; for 2h;
The title compound is commercially available. A mixture of 4-methyl-2-methoxy-3- nitropyridine (4.5 g, 26.8 mmol), NH4CI (7.16 g, 133.9 mmol) and Fe powder (7.5 g, 133.9 mmol) in ethanol (50 mL) was stirred at 25 C. The mixture was slowly heated to 90 C and stirred at this temperature for 2 h. The reaction mixture was filtered through a plug of celite and the celite plug was washed with ethanol (50 mL). The combined filtrates were evaporated to dryness. The remanens was diluted with water (50 mL) and the mixture was extracted with EtOAc (100 mL). The organic layer was dried over Na2S04. Evaporation to dryness gave the title compound as a solid (3.5 g, 81 %). 1 H NMR (CDCI3, 400 MHz) delta 7.50-7.49 (1 H, d, J = 5.2 Hz), 6.62-6.61 (1 H, d, J = 5.2 Hz), 3.97 (3H, s), 3.79-3.69 (2H, br s), 2.15 (3H, s).
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