反应详情

温度

56 °C

Lithium chloride (0.472 g, 11.14 mmol) and lithium formate (0.579 g, 11.14 mmol) were combined in a sealable dried tube. DMF (10 mL), 5-fluoro-3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridine-4-carbaldehyde (1.650 g, 3.71 mmol), acetic anhydride (0.702 mL, 7.43 mmol) and diacetoxypalladium (0.083 g, 0.371 mmol) were added. N-Ethyl-N-isopropylpropan-2-amine (1.294 mL, 7.43 mmol) was added and the mixture was sealed and heated at 56° C. for 3 h. The reaction mixture was taken up in MeOH/DCM (20%) and filtered. The yellow solution was concentrated and the residue was dissolved in MeOH/DCM (10%) and washed with aqueous HCl (0.1N). The aqueous phase was extracted two more times. The organics were combined, dried over MgSO4 and concentrated to an orange oil, which was triturated in ether (300 mL). The precipitate was filtered and dried in vacuo to afford the title compound as light yellow solid (1.15 g, 77%). 1H NMR (400 MHz, DMSO-d6) δ 2.37 (s, 3H) 7.47 (d, J=8.08 Hz, 2H) 8.10 (d, J=8.10 Hz, 2H) 8.54-8.65 (m, 2H) 10.60 (s, 1H) 13.45 (br. s., 1H). [M+H] calc'd for C15H10FIN2O3S, 363; found, 363.4.

1. customthe mixture was sealed
2. filtrationfiltered
3. concentrationThe yellow solution was concentrated
4. dissolutionthe residue was dissolved in MeOH/DCM (10%)
5. washwashed with aqueous HCl (0.1N)
6. extractionThe aqueous phase was extracted two more times
7. dry with materialdried over MgSO4
8. concentrationconcentrated to an orange oil, which
9. customwas triturated in ether (300 mL)
10. filtrationThe precipitate was filtered
11. customdried in vacuo