反应详情

A solution of N-allyl-N-(2-bromo-6-methoxy-pyridin-3-yl)-2,2,2-trifluoro-acetamide (5.54 g, 16.3 mmol), palladium acetate (147 mg, 0.65 mmol), tetra(n-butylammonium) chloride (4.99 g, 17.9 mmol) and triethylamine (3.72 g, 26.8 mmol) in anhydrous DMF (35 mL) is stirred at 10° C. under N2 for an hour. DMF is evaporated off, and the residue is mixed with water (20 mL) and stirred at rt overnight. EtOAc (50 mL) is added. The organic layer is separated, dried (Na2SO4), filtered, and concentrated in vacuo. The residue is purified by silica gel column chromatography eluting with 30-70% EtOAc in heptane to afford 5-methoxy-3-methyl-1H-pyrrolo[3,2-b]pyridine (2.62 g) as a solid. 1H NMR (300 MHz, CDCl3): δ 2.38 (s, 3H), 4.05 (s, 3H), 6.62 (s, H), 7.12 (s, H), 7.54 (d, H), 7.94 (br, N—H).

1. customDMF is evaporated off
2. additionthe residue is mixed with water (20 mL)
3. additionEtOAc (50 mL) is added
4. customThe organic layer is separated
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe residue is purified by silica gel column chromatography
9. washeluting with 30-70% EtOAc in heptane