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With palladium diacetate; triethylamine; In N,N-dimethyl-formamide; at 100℃;
Step 2: synthesis of 5-chloro-lH-pyrrolo[3,2-b]pyridine-2-carboxylic acid 11-b2-oxopropanoic acid (36.22 g, 411.31 mmol), palladium(II)acetate (7.74 g, 34.15 mmol) and Et3N (69.11 g, 682.94 mmol) were added to a solution of 2-bromo-6- chloropyridin-3 -amine 11-a (32.20 g, 155.21 mmol) and TPP (35.83 g, 136.59 mmol) in dry DMF (300 ml). The reaction mixture was stirred at 100C overnight. The solvent was then evaporated, water was added and the water layer was washed with EtOAc. The water layer was acidified with cone. HCl. The precipitate was filtered off and dried, yielding 25.21 g of the wanted product 11-b (82.6 %). m/z = 197.1 (M+H)+, CI pattern.
82.6%
With palladium diacetate; triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; at 100℃;
2-oxopropanoic acid (36.22 g, 411.31 mmol), palladium(II)acetate (7.74 g, 34.15 mmol) and Et3N (69.11 g, 682.94 mmol) were added to a solution of 2-bromo-6- chloropyridin-3-amine 28-b (32.20 g, 155.21 mmol) and TPP (35.83 g, 136.59 mmol) in dry DMF (300 ml). The reaction mixture was stirred at 100C overnight. The solvent was then evaporated, water was added and the water layer was washed with EtOAc. The water layer was acidified with cone. HC1. The precipitate was filtered off and dried, yielding 25.21 g of the intermediate 28-c (82.6 %)
82.6%
With palladium diacetate; triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; at 100℃;
2-oxopropanoic acid (36.22 g, 411.31 mmol), palladium(II)acetate (7.74 g,34.15 mmol) and Et3N (69.11 g, 682.94 mmol) were added to a solution of<strong>[1050501-88-6]2-bromo-6-chloropyridin-3-amine</strong> 49-a (32.20 g, 155.21 mmol) and TPP (35.83 g, 136.59 mmol)in dry DMF (300 ml). The reaction mixture was stirred at 100C overnight. The solvent was then evaporated, water was added and the water layer was washed withEtOAc. The water layer was acidified with cone. HCl. The precipitate was filtered offand dried, yielding 25.21 g of the wanted product 49-b (82.6 %).m/z = 197.1 (M+It.
82.6%
With palladium diacetate; triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; at 100℃;
Step 2: synthesis of 5-chloro-1H-pyrrolo[3,2-bjpyridine-2-carboxylic acid (intermediate 20b)2-oxopropanoic acid (36.22 g, 411.31 mmol), palladium(II)acetate (7.74 g, 34.15 mmol) and Et3N (69.11 g, 682.94 mmol) were added to a solution of 2-bromo-6- chloropyridin-3-amine 20a (32.20 g, 155.21 mmol) and TPP (35.83 g, 136.59 mmol) in dry DMF (300 ml). The reaction mixture was stirred at 100C overnight. The solvent was then evaporated, water was added and the water layer was washed with EtOAc.The water layer was acidified with conc. HC1. The precipitate was filtered off and dried, yielding 25.21 g of the wanted product 20b (82.6 %). m/z = 197.1 (M+H), Cl pattern.
82.6%
With palladium diacetate; triethylamine; triphenylphosphine; In water; N,N-dimethyl-formamide; at 100℃;
2-oxopropanoic acid (36.22 g, 411.31 mmol), palladium(II)acetate (7.74 g, 34.15 mmol) and Et3N (69.11 g, 682.94 mmol) were added to a solution of <strong>[1050501-88-6]2-bromo-6-chloropyridin-3-amine</strong> 49-a (32.20 g, 155.21 mmol) and TPP (35.83 g, 136.59 mmol) in dry DMF (300 ml). The reaction mixture was stirred at 100 C. overnight. The solvent was then evaporated, water was added and the water layer was washed with EtOAc. The water layer was acidified with conc. HCl. The precipitate was filtered off and dried, yielding 25.21 g of the wanted product 49-b (82.6%). m/z=197.1 (M+1)+.
With palladium diacetate; triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; at 115℃; for 18h;Inert atmosphere;
To the mixture of <strong>[1050501-88-6]2-bromo-6-chloropyridin-3-amine</strong> (5 g, 24.4 mmol), Pd(OAc)2 (1.09 g, 4.88 mmol), PPh3 (1.91 g, 7.32 mmol) and triethylamine (10.8 g, 107.3 mmol) in DMF (30 mL) in N2 atmosphere, was added 2-oxopropanoic acid (5.69 g, 64.6 mmol) by a syringe. The resulting mixture was heated at 115C for l8hrs under N2. The reaction mixture was cooled to room temperature and poured into water (200 mL) The resulting precipitate was filtered and the filtrate was washed with EA(30 mL x 3). The pH of aqueous phase was adjusted with iN aq. HC1 solution to pH 4, and the resulting precipitate was collected by filtration and dried by reduced pressure to give 5-chloro-1H-pyrrolo[3,2-bjpyridine-2- carboxylic acid (2.44 g, 51%) as a solid. HPLC/UV purity: 90%; LC-MS (ESI): 197.1 (M + 1).
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