Ethanone,1-(1H-pyrrolo[2,3-b]pyridin-3-yl)-(9CI)

Solid

the 7-azaindole (0. 59g, 5mmol) dissolvedin 80mL of dichloromethane, added Aluminum trichloride (3. 39g, 25mmol), slowlydropwise added Acetyl chloride (3. 4mL, 47. 8mmol), at room temperature keepthe reaction for 10h. The reaction solution was placed in an ice bath, slowlyadded 20mL of methanol to quench the reaction. the reaction mixture wasconcentrated and in the residue added 30mL of water , the pH value of reaction solution wasadjusted to approx 4 with 1N of Aqueous sodium hydroxide solution, the reactionsolution was extracted with Ethyl acetate (15mLX3), combined the organicphases, washed with saturated brine (20 mLx2) and Dried over anhydrous sodiumsulfate. Filtrated , concentrated and the residue was separated and purifiedwith column chromatography (Eluent, petroleum ether: ethyl acetate = 1: 1, v /v) to obtain pale yellow solid 0.72g, yield 90percent.A solution of 7-azaindole (590 mg, 5 mmol) in 80 mL of DCM was added AlCl3 (3.39 g, 25 mmol). Acetyl chloride (3.4 mL, 47.8 mmol) was added slowly and the reaction was allowed to proceed for 10 h at room temperature. The reaction mixture was quenched by adding 20 mL of methanol slowly and the reaction mixture was concentrated. To the residue, 30 mL of water was added. The mixture was adjusted to pH ~ 4 with IN NaOH, extracted with EtOAc (15 mL × 5), dried over anhydrous sodium sulfate and concentrated. Analytical separation (Ρ: Ε = 1: 1) gave a white solid (22-1) in 82.5percent yield. Starting from 22-1, the title compound was synthesized according to the synthesis scheme of The product 22 was a white solid with a 4.9percent yield in two steps and a MP of 147.8-148.2 ° C.To a suspension of AlCl1 -( 1 H-pyrrol o [2 , 3 -b)pγ ri din-3 -vDethanone[0244] To a suspension Of AlClA solution of 6.89 g (43.0 mmol) of the 7-azaindole (0. 59g, 5mmol) dissolvedin 80mL of dichloromethane, added Aluminum trichloride (3. 39g, 25mmol), slowlydropwise added Acetyl chloride (3. 4mL, 47. 8mmol), at room temperature keepthe reaction for 10h. The reaction solution was placed in an ice bath, slowlyadded 20mL of methanol to quench the reaction. the reaction mixture wasconcentrated and in the residue added 30mL of water , the pH value of reaction solution wasadjusted to approx 4 with 1N of Aqueous sodium hydroxide solution, the reactionsolution was extracted with Ethyl acetate (15mLX3), combined the organicphases, washed with saturated brine (20 mLx2) and Dried over anhydrous sodiumsulfate. Filtrated , concentrated and the residue was separated and purifiedwith column chromatography (Eluent, petroleum ether: ethyl acetate = 1: 1, v /v) to obtain pale yellow solid 0.72g, yield 90%.A solution of 7-azaindole (590 mg, 5 mmol) in 80 mL of DCM was added AlCl3 (3.39 g, 25 mmol). Acetyl chloride (3.4 mL, 47.8 mmol) was added slowly and the reaction was allowed to proceed for 10 h at room temperature. The reaction mixture was quenched by adding 20 mL of methanol slowly and the reaction mixture was concentrated. To the residue, 30 mL of water was added. The mixture was adjusted to pH ~ 4 with IN NaOH, extracted with EtOAc (15 mL × 5), dried over anhydrous sodium sulfate and concentrated. Analytical separation (Rho: Epsilon = 1: 1) gave a white solid (22-1) in 82.5% yield. Starting from 22-1, the title compound was synthesized according to the synthesis scheme of The product 22 was a white solid with a 4.9% yield in two steps and a MP of 147.8-148.2 C.To a suspension of AlCl3 (5.6 g, 42 mmol) in dry dichloromethane (200mL), solid 1H-pyrrolo[2, 3-b]pyridine (1 g, 8.4 mmol) was added and the reaction mixture was stirred at RT for 1 h. Acetyl chloride (3 mL, 42 mmol) was cautiously dropped in and the reaction mixture was stirred overnight at RT. After cooling in ice bath the mixture was cautiously quenched with methanol (40 mL), concentrated to dryness and purified by flash chromatography on silica gel (eluant: dichloromethane/methanol 10:1). Obtained 1.05 g (6.5 mmol, 78% yield) of desired 3-acetyl, 7-azaindole.1 -( 1 H-pyrrol o [2 , 3 -b)pgamma ri din-3 -vDethanone[0244] To a suspension Of AlCl3 (4.91 g, 36.8 mmol) in CH2Cl2 (100 mL) at rt was added lH-pyrrolo[2}3-6]pyridine (899 mg, 7.61 mmol). After 60 min AcCl (2.7 mL, 37.8 mmol) was added dropwise and the mixture was stirred overnight. The reaction was quenched by carefull addition of MeOH (35 mL) and evaporated to dryness. Saturated aqueous NaHCO3 (150 mL) and EtOAc (100 mL) were added to the residue followed by vigorous stirring. The aqueous layer was extracted with EtOAc (2x 100 mL), and the combined organic layers were dried over Na2SO4 and evaporated to dryness to give the title compound as colorless crystals (803 mg, 66%).[0245] 1H NMR (400 MHz, CD3OD) delta 8.70 (dd, J = 7.9, 1.6 Hz, IH), 8.37-8.35 (m, 2H), 7.37 (dd, J= 7.9, 5.0 Hz, I H), 2.58 (s, 3H).A solution of 52.8 ml (229 mmol) of tin tetrachloride in 100 ml of chlorobenzene is added dropwise with ice-cooling to a solution of 15.5 g (131 mmol) of 7-azaindole in 100 ml of chlorobenzene, and the mixture is subsequently stirred for 15 minutes with ice-cooling. A solution of 16.2 ml (227 mmol) of acetyl chloride in 100 ml of chlorobenzene is then added dropwise, and the reaction mixture is stirred at room temperature for 24 hours. The resultant precipitate is filtered off with suction, washed with dichloromethane, and the residue is dried in vacuo. This solid is then stirred with 100 ml of water and filtered off with suction. The residue is stirred with 2 N aqueous sodium hydroxide solution, filtered off with suction, washed with water and dried in vacuo. This solid is extracted a number of times with hot ethyl acetate. The ethyl acetate solution is evaporated: General procedure: To a 20 ml or 40 ml viale quipped with a stir bar was added photocatalyst, nitrogen nucleophile, iodomesitylene dicarboxylate, copper salt, and ligand. Dioxane was added followed by addition of the base. The solution was sonicated for 1-3 min until it became homogeneous. Next, the solution was degassed by sparging with nitrogen for 5-10 min before sealing with Parafilm. The reaction was stirred and irradiated using two 34-W blue LED lamps (3 cm away, with cooling fan to keep the reaction at room temperature) for 1 h. The reaction mixture was removed from the light, cooled to ambient temperature, diluted with water (15 ml) and ethyl acetate (25 ml), and the aqueous layer was extracted with ethyl acetate (3 × 25 ml). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel to afford the desired decarboxylative C-N coupling product. For aniline substrates, a solution of these nitrogen nucleophiles in dioxane was used; additionally, if the iodomesitylene dicarboxylate is a liquid, its solution in dioxane was used.Step a: 2-Bromo-theCompound (0. 48g, 3mmol) of PreparationExample 23a dissolved in 5mL of DMF, added Potassium carbonate (0. 83g, 6mmol)and under 50 C the reaction was stirred for 15min. added 2-bromoethyl methyl ether(0. 52g, 3. 6mmol) and continued at 50 C keep the reaction for 2h.in the reaction solution added 50mL ofwarer, the reaction solution was extracted with Ethyl acetate (15mLX3), combined the organic phases, washed with saturated brine (20 mLx2) and Driedover anhydrous sodium sulfate. Filtrated , concentrated and the residue wasseparated and purified with column chromatography (Eluent, petroleum ether:ethyl acetate = 2: 1, v / v) to obtain pale yellow solid 0.50g, yield 75%.

Molecular Weight:160.17
XLogP3:1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:160.063662883
Monoisotopic Mass:160.063662883
Topological Polar Surface Area:45.8
Heavy Atom Count:12
Complexity:193
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes