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With potassium acetate In dichloromethane; dimethyl sulfoxide at 80℃;
Example 46; 6-(2,3-Dihydro-1H-indol-5-yl)-4-morpholin-4-yl-1-(1-pyridin-3-ylmethyl-piperidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidine (Scheme 36)1 mmol (198 mg) 5-bromoindoline, 1.5 mmol (381 mg) bispinacolatodiboron, 0.1 mmol (73 mg) Pd(dppf)Cl2.CH2Cl2 and 3 mmol (296 mg) KOAc are suspended in DMSO and heated at 80 C overnight. The mixture is diluted with EtOAc, filtered over Celite and concentrated. Flash chromatography (5-20percent EtOAc in hexanes) gave 69 mg (28percent) of the boronate. This was added to a solution of 50 mg 6-Chloro-4-morpholin-4-yl-1-(1-pyridin-3-ylmethyl-piperidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidine in 2 mL DME and 250 uL of a 2M Na2CO3 solution. 10 mol percent Pd(PP3)4 was added and the mixture was stirred at 95C overnight. The solvents were removed and the product was purified by HPLC (TFA buffers).
With copper(l) iodide; sodium L-prolinate; In dimethyl sulfoxide; at 95℃; for 24h;
5-bromoindoline (1g, 5.05mmol), L-proline sodium salt (139 mg, 1.0mmol), cuprous iodide (96 mg, 0 . 50mmol) and sodium methylsulfinate (618 mg, 6.05mmol) dissolved in dimethyl sulfoxide (10 ml). At 95 C stirring for 24 hours. The reaction is cooled down to the room temperature after the addition of water (50 ml) quenching after dichloromethane is used for extraction (50 ml × 2), combined with the organic phase, saturated sodium chloride solution (30 ml), anhydrous sodium sulfate drying, filtering, the filtrate is concentrated under reduced pressure to obtain a yellow solid title compound (0.99g, yield 99.4%).
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