反应详情

温度

125 °C

Ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (50.0 mg, 0.222 mmol), phenyl boronic acid (32.4 mg, 0.266 mmol) and potassium carbonate (0.332 mL, 0.665 mmol) were added to tetrahydrofuran (1.5 mL) in a microwave vial. The solution was purged with nitrogen for 5 minutes and PdCl2(dppf)-CH2Cl2 (18 mg, 0.022 mmol) was then added. The reaction was sealed and heated at 125° C. by microwave irradiation for 30 minutes. The reaction mixture was diluted with EtOAc and washed with saturated sodium bicarbonate, dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification of desired product was carried out by reverse phase HPLC using an acetonitrile gradient in water with 0.1% TFA modifier. Pure fractions were pooled and concentrated under reduced pressure. Saturated aqueous sodium bicarbonate and EtOAc were added to the residue. The organic layer was separated and the aqueous layer was then extracted with EtOAc (×3). The combined organic layers were then washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford the product as a solid. LRMS (ESI) calc'd for C15H14ClN3O2 [M+H]+: 268, found 268. 1H NMR (600 MHz, DMSO-D6) δ 13.01 (s, 1H), 8.91 (s, 1H), 8.30 (s, 1H), 7.63 (m, 2H), 7.49 (m, 3H), 3.82 (q, 2H, J=7.04 Hz), 0.78 (t, 3H, J=7.04 Hz).

1. customThe solution was purged with nitrogen for 5 minutes
2. customThe reaction was sealed
3. washwashed with saturated sodium bicarbonate
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customPurification of desired product
8. concentrationconcentrated under reduced pressure
9. additionSaturated aqueous sodium bicarbonate and EtOAc were added to the residue
10. customThe organic layer was separated
11. extractionthe aqueous layer was then extracted with EtOAc (×3)
12. washThe combined organic layers were then washed with brine
13. dry with materialdried over sodium sulfate
14. filtrationfiltered
15. concentrationconcentrated under reduced pressure