* 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 manganese(IV) oxide In dichloromethane at 20℃; for 48 h;
Method of synthesising quinoline D*.8D*.7 D*.8Alcohol D*.7 (716 mg, 2.70 mmol) is placed in DCM (9 mL), combined with Mn02 (705 mg, 8.12 mmol) and stirred for 2 d at 20°C. The reaction mixture is filtered through Celite, the solvent is eliminated and product D*.8 (577 mg, 63 percent) is obtained.
63%
With manganese(IV) oxide In dichloromethane at 20℃; for 48 h;
Method of Synthesising Quinoline D*.8Alcohol D*.7 (716 mg, 2.70 mmol) is placed in DCM (9 mL), combined with MnO2 (705 mg, 8.12 mmol) and stirred for 2 d at 20° C. The reaction mixture is filtered through Celite, the solvent is eliminated and product D*.8 (577 mg, 63percent) is obtained.
General procedure: A mixture of 2-aminopyridine-5-carboxylic acid (2) or substituted 2-aminobenzothiazole (3.0 mmol) in MeOH-DCM (2:3, 15.0 mL) and aldehyde (3.0 mmol) containing 5 mol% of Sc(OTf)3 was stirred for 1 h at room temperature, followed by the addition of 3 mmol of the phenyl isocyanide, and the mixture was stirred for another 12 h at rt. Then 1 mL of hexane was added and the resulting yellowish solid was filtered, washed three times with hexane-ethyl acetate mixture (5:1, 20 mL) and triturated with ethyl acetate-hexane. The crude product was used in the next step without further purification.
General procedure: A mixture of 2-aminopyridine-5-carboxylic acid (2) or substituted 2-aminobenzothiazole (3.0 mmol) in MeOH-DCM (2:3, 15.0 mL) and aldehyde (3.0 mmol) containing 5 mol% of Sc(OTf)3 was stirred for 1 h at room temperature, followed by the addition of 3 mmol of the phenyl isocyanide, and the mixture was stirred for another 12 h at rt. Then 1 mL of hexane was added and the resulting yellowish solid was filtered, washed three times with hexane-ethyl acetate mixture (5:1, 20 mL) and triturated with ethyl acetate-hexane. The crude product was used in the next step without further purification.
Step 2; 6-Bromoquinoline-3-carbaldehyde 2 (2.8 g, 12.0 mmol) and methyl(triphenylphosphoranylidene) acetate (4.0 g, 12.0 mmol) were dissolved in dry THF (50 mL) and heated to 50 C. After 40 min the solution was evaporated to dryness under reduced pressure. Purification using silica chromatography (hexane to 60% ethyl acetate in hexane gradient) gave methyl 3-(6-bromoquinolin-3-yl)acrylate 3 as a mixture of E and Z isomers.
Step 1; 5-Bromo-2-nitrobenzaldehyde 1 (6.03 g, 26.2 mmol) was dissolved in MeOH (200 mL) and treated with 5N HC1 (10 mL). The mixture was heated to 70 C and iron powder (7.32 g, 131 mmol) was added in five portions every 5 min. Upon completion (by TLC) the reaction was cooled and DCM (200 mL) was added before filtering through a pad of celite. The filtrate was concentrated under reduced pressure to 150 mL. To this material, a solution of 1,1,3, 3-tetramethoxypropane (9.52 ml, 57.7 mmol) in 5N HC1 (10 mL) pre- mixed for 45 min was added. The reaction mixture was stirred at 80 C for 60 min. Toluene (100 mL) and acetic acid (40 mL) were added and the solution was heated to 110 C for 3 h, then cooled and evaporated to dryness under reduced pressure. The crude material was purified using silica chromatography (20-60% ethyl acetate in hexane gradient) to give 6-bromoquinoline-3-carbaldehyde 2.
Method of synthesising quinoline D.62Aldehyde D*.8 (82 mg, 0.35 mmol) is placed in DCM (1 .5 mL), combined with amine ED.14 (0.18 mL, 1 .39 mmol) and CH3COOH (0.09 mL) and stirred for 10 min at 20C. Then NaBH(OAc)3 (1 10 mg, 0.52 mmol) is added, the mixture is stirred for 12 h at 20C, the solvent is eliminated, the residue is purified by chromatography (20:80 to 80:20 in 15 min CH3CN/H20) and quinoline D.62 (68 mg, 59 %) is obtained.
59%
Method of Synthesising Quinoline D.62Aldehyde D*.8 (82 mg, 0.35 mmol) is placed in DCM (1.5 mL), combined with amine ED.14 (0.18 mL, 1.39 mmol) and CH3COOH (0.09 mL) and stirred for 10 min at 20 C. Then NaBH(OAc)3 (110 mg, 0.52 mmol) is added, the mixture is stirred for 12 h at 20 C., the solvent is eliminated, the residue is purified by chromatography (20:80 to 80:20 in 15 min CH3CN/H2O) and quinoline D.62 (68 mg, 59%) is obtained.
With manganese(IV) oxide; In dichloromethane; at 20℃; for 48h;
Method of synthesising quinoline D*.8D*.7 D*.8Alcohol D*.7 (716 mg, 2.70 mmol) is placed in DCM (9 mL), combined with Mn02 (705 mg, 8.12 mmol) and stirred for 2 d at 20C. The reaction mixture is filtered through Celite, the solvent is eliminated and product D*.8 (577 mg, 63 %) is obtained.
63%
With manganese(IV) oxide; In dichloromethane; at 20℃; for 48h;
Method of Synthesising Quinoline D*.8Alcohol D*.7 (716 mg, 2.70 mmol) is placed in DCM (9 mL), combined with MnO2 (705 mg, 8.12 mmol) and stirred for 2 d at 20 C. The reaction mixture is filtered through Celite, the solvent is eliminated and product D*.8 (577 mg, 63%) is obtained.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
