反应详情

温度

100 °C

A mixture of 4-(1-(4-methoxybenzyl)-3-iodo-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorobenzenamine (0.123 g, 0.25 mmol, prepared according to Example 7, Step B), ±(3S*,4R*)-tert-butyl 4-amino-3-fluoropiperidine-1-carboxylate (0.164 g, 0.750 mmol, prepared according to WO 2006/087543), copper(I)iodide (0.00952 g, 0.0500 mmol), (S)-pyrrolidine-2-carboxylic acid (0.0115 g, 0.100 mmol), K2CO3 (0.173 g, 1.25 mmol), and DMSO (1 mL) was stirred at 100° C. for 3 days. The reaction was partitioned between EtOAc and water. The phases were separated and the aqueous phase was re-extracted with EtOAc (5 mL). The combined organic phases were washed with water, dried (Na2SO4), filtered, and concentrated. The crude was purified by preparative TLC (1 mm thickness, Rf=0.56) eluting with 10% MeOH/CHCl3. LRMS (APCI+): m/z 581 (M+1) detected.

1. customThe reaction was partitioned between EtOAc and water
2. customThe phases were separated
3. extractionthe aqueous phase was re-extracted with EtOAc (5 mL)
4. washThe combined organic phases were washed with water
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated
8. customThe crude was purified by preparative TLC (1 mm thickness, Rf=0.56)
9. washeluting with 10% MeOH/CHCl3