反应详情

To a solution of 3-(benzyloxy)-6-bromopicolinic acid (0.50 g, 1.62 mmol) and HATU (1.23 g, 3.24 mmol) in DMF (5 mL) was added phenylamine (0.52 g, 4.87 mmol) dropwise. After stirring at room temperature overnight, the mixture was concentrated and the residue was diluted with water and extracted with EtOAc. The combined organic phase was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by flash gel chromatography (DCM:MeOH=50:1) to afford the product of N-benzyl-3-(benzyloxy)-6-bromopicolinamide (0.60 g, yield: 93.2%). 1H-NMR (CDCl3, 400 MHz) δ 7.79 (br s, 1H), 7.38˜7.41 (m, 3H), 7.19˜7.32 (m, 9H), 5.18 (s, 2H), 4.58 (d, J=5.6 Hz, 2H). MS (M+H)+: 397/399.

1. concentrationthe mixture was concentrated
2. additionthe residue was diluted with water
3. extractionextracted with EtOAc
4. washThe combined organic phase was washed with brine
5. dry with materialdried over Na2SO4
6. concentrationconcentrated
7. customThe residue was purified by flash gel chromatography (DCM:MeOH=50:1)