反应详情

温度

150 °C

To a solution of 2-bromo-7-(1H-indol-5-yl)-5-tosyl-5H-pyrrolo[3,2-b]pyrazine [Intermediate AV] (65 mg, 0.14 mmol) in CH3CN (1 mL) in a Personal Chemistry microwave reaction vial was added 3,4,5-trimethoxyphenylboronic acid (30 mg, 0.14 mmol), bis(triphenylphosphine)-palladium(II) dichloride (7.0 mg, 0.010 mmol), and 1 M Na2CO3 (1 mL). The resulting mixture was de-gassed with Ar for 10 min, after which it was heated at 150° C. for 10 min in a Personal Chemistry Optimizer. The organic layer was separated, filtered, and concentrated in vacuo. The residue was dissolved in MeOH (3 mL) and acetone (2 mL), and 2 M NaOH (1.5 mL) was added. The resulting mixture was stirred at 65° C. for 30 min, after which it was partitioned between EtOAc and 1 M NaOH. The organic layer was separated, dried over MgSO4, filtered, and stripped to give a residue which was purified by preparatory HPLC to give the title compound as a yellow solid. HPLC retention time: 2.25 minutes; MS ESI (m/z) 401.2 (M+1)+, calc. 400.

1. customThe resulting mixture was de-gassed with Ar for 10 min
2. customThe organic layer was separated
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. dissolutionThe residue was dissolved in MeOH (3 mL)
6. additionacetone (2 mL), and 2 M NaOH (1.5 mL) was added
7. customafter which it was partitioned between EtOAc and 1 M NaOH
8. customThe organic layer was separated
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. customto give a residue which
12. customwas purified by preparatory HPLC