反应详情

Methyl 4-bromo-3-fluorobenzoate (2.261 g, 9.702 mmol) [CAS 849758-12-9] was added to a solution of 1,2,3,6-tetrahydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridine (3 g, 9.702 mmol) [CAS 375853-82-0] (synthesis described in WO 2004072025 A2 20040826) in 1,4-dioxane (21 ml) and an aqueous saturated solution of NaHCO3 (18 ml). The resulting solution was degassed using a stream of nitrogen and Pd(PPh3)4 (0.561 g, 0.485 mmol) was added to this solution. The reaction was then microwaved in a sealed tube at 150° C. for 5 minutes. The resulting cooled reaction mixture was then diluted with EtOAc and filtered through a pad of diatomaceous earth. The filtrate was collected, dried over Na2SO4 and concentrated in vacuo. The crude reaction mixture was then purified by column chromatography (silica gel; DCM to DCM/EtOAc up to 6% as eluent). The desired fractions were collected and evaporated in vacuo to yield D22 (2.107 g, 65%).

1. customThe resulting solution was degassed
2. additionwas added to this solution
3. customThe reaction was then microwaved in a sealed tube at 150° C. for 5 minutes
4. temperatureThe resulting cooled
5. customreaction mixture
6. filtrationfiltered through a pad of diatomaceous earth
7. customThe filtrate was collected
8. dry with materialdried over Na2SO4
9. concentrationconcentrated in vacuo
10. customThe crude reaction mixture
11. customwas then purified by column chromatography (silica gel; DCM to DCM/EtOAc up to 6% as eluent)
12. customThe desired fractions were collected
13. customevaporated in vacuo