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With potassium fluoride; copper(l) iodide; In 1-methyl-pyrrolidin-2-one; at 115 - 125℃; for 6.08333 - 6.16667h;
Into a 250 ml 3-necked round bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed NMP (80 ml). To the above was added KF (6.8 g, 0.12 mol) and CuI (15 g, 0.08 mol). After stirring 5-10 min, XIV-A-95 (11 g, 0.04 mol) and ClF2CCO2Et (18 g, 0.12 mol) were added. The resulting solution was stirred for 6 h while the temperature was maintained at 115-125 C. After cooling, 300 ml CH2Cl2 was added to the reaction system. The organic layer was washed with saturated NaCl solution (80 ml×5) and dried with Na2SO4. After evaporating the solvent, the residue was purified by column chromatography (eluant: PE:EtOAc=10:1) and compound XIV-B-95 was collected (4.65 g, 53.1%) as a yellow solid (m.p.: 38-40 C.)
(3.5 mmol) of 2-iodo-5-bromothiopyridine was dissolved in 5 ml of 4-dioxane,0.128 (0.1 mole) of tetrakis (triphenylphosphine) palladium was added under nitrogen atmosphere,80 ° (reaction 211. To room temperature,Followed by the addition of 9 ml of a 21percent aqueous sodium carbonate solution,A solution of 0.8 g (4.2 mmol)1-Phenyl-1H-pyrazole-4-boronic acid in 1,4-dioxane5ml, rose to 100 ° CThe reaction was continued for 4 h.After cooling to room temperature, it was poured into ice water, solid precipitated, stirred until solid precipitated completely,The product was purified by silica gel column chromatography (eluent:Ethyl acetate / petroleum ether = l / lO, V: V) gave a white solid intermediate 10h 0.86 g, yield 82percent
iPrMgCl*LiCl (Turbo Grignard, 1.3 mol/L in tetrahydrofuran, 25.6 mL) is added dropwise to a flask charged with a stir bar, 2-iodo-5-bromo-pyridine (9.00 g), and tetrahydrofuran (180 mL) and chilled to -30° C. The mixture is stirred in the cooling bath for 1 h. 2-Chloro-N-methoxy-N-methylacetamide (4.58 g) dissolved in tetrahydrofuran (20 mL) is added dropwise over 5 min. The mixture is stirred for 30 min and then quenched by the addition of aqueous 1 M HCl solution. The mixture is concentrated, and the aqueous residue is extracted with ethyl acetate. The combined extract is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 20:1?1:1) to give the title compound. Mass spectrum (ESI+): m/z=234/236/238 (Br+Cl) [M+H]+.
PrMgCI*LiCI (Turbo Grignard, 1 .3 mol/L in tetrahydrofuran, 25.6 mL) is added dropwise to a flask charged with a stir bar, 2-iodo-5-bromopyridine (9.00 g), and tetrahydrofuran (180 mL) and chilled to -30 °C. The mixture is stirred in the cooling bath for 1 h. 2-Chloro-N-methoxy-N-methylacetamide (4.58 g) dissolved in tetrahydrofuran (20 mL) is added dropwise over 5 min. The mixture is stirred for 30 min and then quenched by the addition of aqueous 1 M HCI solution. The mixture is concentrated, and the aqueous residue is extracted with ethyl acetate. The combined extract is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 20:1?1 :1 ) to give the title compound. Mass spectrum (ESI+): m/z = 234/236/238 (Br+CI) [M+H]+.
PrMgCI*LiCI (Turbo Grignard, 1 .3 mol/L in tetrahydrofuran, 25.6 mL) is added dropwise to a flask charged with a stir bar, 2-iodo-5-bromopyridine (9.00 g), and tetrahydrofuran (180 mL) and chilled to -30 C. The mixture is stirred in the cooling bath for 1 h. <strong>[67442-07-3]2-chloro-N-methoxy-N-methylacetamide</strong> (4.58 g) dissolved in tetrahydrofuran (20 mL) is added dropwise over 5 min. The mixture is stirred for 30 min and then quenched by the addition of aqueous 1 M HCI solution. The mixture is concentrated, and the aqueous residue is extracted with ethyl acetate. The combined extract is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 20:11 :1 ) to give the title compound. Mass spectrum (ESI+): m/z = 234/236/238 (Br+CI) [M+H]+.
9-(5-bromopyridin-2-yl)-9H-3,9'-bicarbazole[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
2.43 g
With potassium phosphate; copper(l) iodide; trans-1,2-Diaminocyclohexane; In 1,4-dioxane; for 12h;Reflux;
9H-3,9'-bicarbazole (5.0g), 5-bromo-2-iodo-pyridine (3.9g), CuI (0.26g), K3PO4 (0.26g), trans-1,2-dicyclohexyldiamine (0.164mL) Was dissolved in 1,4-dioxane and stirred under reflux for 12 hours. Extracted with dichloromethane and distilled water, and filtered the organic layer using silica gel. After removal of the organic solution, the compound was purified by silica gel column to obtain compound 9- (5-bromopyridin-2-yl) -9H-3,9'-bicarbazole (2.43 g).
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