* 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 hydrogenchloride In tetrahydrofuran; water at 60℃; for 1 h;
A solution of 2-chloro- 5-(methoxymethoxy)pyridine-4-carbaldehyde ( 12 g, 59.52 mmol, 1.00 equiv) in tetrahydrofuran (80 mL) and 3M HCl (130 mL) was stirred for 1 h at 60°C. The reaction mixture was cooled to rt and the pH value of the solution was adjusted to 7 with 5percent aqueous sodium carbonate solution. The organic layer was collected and the aqueous layer was extracted with 400 mL of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1 :3) to give 6 g (64percent) of 2-chloro-5-hydroxypyridine-4-carbaldehyde as a light yellow solid. TLC: petroleum ether: ethyl acetate=2:1 , Rf = 0.3.
Reference：
[1] Patent: WO2013/127268, 2013, A1, . Location in patent: Page/Page column 95; 96
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 18, p. 8345 - 8368
2
[ 41288-96-4 ]
[ 1060804-53-6 ]
Reference：
[1] Patent: WO2013/127268, 2013, A1,
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 18, p. 8345 - 8368
3
[ 877133-56-7 ]
[ 1060804-53-6 ]
Reference：
[1] Patent: WO2013/127268, 2013, A1,
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 18, p. 8345 - 8368
100 mL of CH2Cl2 was put into the compound 2-chloro-5-hydroxy-pyridine-4-carbaldehyde (13.7 g, 87 mmol) and agitated, and triethylamine (13.3 g, 130.5 mmol), and trifluoroacetic anhydride (25.8 g, 130.5 mmol) were slowly dropped thereto. The mixture was agitated at normal temperature for 2 hours, water and CH2Cl2 were added to separate the organic layer, and the organic extract was dried over magnesium sulfate and concentrated under the vacuum. It was purified with CH2Cl2/EtOH to prepare the compound C-26 (22.7 g, yield 90%). MS [M+H]+=289
To a solution of aldehyde 21 a (4.4 g, 27.9 mmol, Anichem) in isopropyl alcohol (180 mL) is added hydroxylamine hydrochloride (5.8 g, 83.8 mmol). The solution is heated to reflux for 1 h, then cooled to RT and the solvent is removed in vacuo. The residue is diluted with EtOAc, washed with sodium bicarbonate solution and dried (Na2S04) to obtain the corresponding oxime. Cyanuric chloride (9.1 g, 49.3 mmol) is added portionwise to DMF (40 mL) at 0C while maintaining the temperature below 25C until cyanuric chloride completely consumed (~1 h). The obtained oxime is added to the solution of DMF at the same temperature and stirred for 1 h. The reaction mixture is quenched by adding water, extracted with EtOAc and washed with NaHC03 solution and brine. The organic layer is dried (Na2S04) and concentrated to give cyanide 21 b.
With hydrogenchloride; In tetrahydrofuran; water; at 60℃; for 1h;
A solution of 2-chloro- 5-(methoxymethoxy)pyridine-4-carbaldehyde ( 12 g, 59.52 mmol, 1.00 equiv) in tetrahydrofuran (80 mL) and 3M HCl (130 mL) was stirred for 1 h at 60C. The reaction mixture was cooled to rt and the pH value of the solution was adjusted to 7 with 5% aqueous sodium carbonate solution. The organic layer was collected and the aqueous layer was extracted with 400 mL of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1 :3) to give 6 g (64%) of 2-chloro-5-hydroxypyridine-4-carbaldehyde as a light yellow solid. TLC: petroleum ether: ethyl acetate=2:1 , Rf = 0.3.
With potassium carbonate; In N,N-dimethyl-formamide; at 50℃; for 2h;
A solution of <strong>[1060804-53-6]2-chloro-5-hydroxypyridine-4-carbaldehyde</strong> (5.7 g, 36. 18 mmol, 1.00 equiv), methyl 2-bromoacetate (7.8 g, 50.99 mmol, 1 .41 equiv) and potassium carbonate (6.5 g) in DMF (100 mL) was stirred for 2 h at 50C The resulting solution was diluted with 400 mL of ethyl acetate and washed with 2x200 mL of FL . The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether ( 1 :3) to yield 5.5 g (66%) of methyl 2-[(6-chloro-4-formylpyridin-3-yl)oxy]acetate as a light yellow solid. TLC: petroleum ethe ethyl acetate=2: 1 , Rf = 0.3.
With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 8h;
j00489j To a mixture of <strong>[1060804-53-6]2-chloro-5-hydroxyisonicotinaldehyde</strong> (4.0 g, 25 mmol) and methyl 2- bromoacetate (5.8 g, 38 mmol) in N,N-dimethylformamide (40 mL) under nitrogen at room temperature was added potassium carbonate (6.9 g, 50 mmol). The reaction mixture was stirred at 80 C for 8 hours, then diluted with water (100 mL) and extracted with ethyl acetate (3 x 100 mL). The combined organic layers were washed with brine (2 x 100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel silica gel chromatography [petroleum ether: ethyl acetate = 25:11 to give compound B-109 (4.2 g, 79% yield) as a white solid. LCMS (E): tR=0.68 mm., 212.6 mlz (M+1).
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