反应详情

温度

80 °C

A flask is charged with 6-chloro-1-Boc-indole-2-boronic acid (0.839 g, 2.83 mmol), 1-benzyloxy-3-bromo-pyridine (0.500 g, 1.89 mmol), potassium phosphate (1.2 g, 5.67 mmol) and DMF (5 mL). The flask is evacuated and filled with nitrogen thrice and Pd(PPh3)4 (0.164 g, 0.141 mmol) is added. The flask is evacuated and filled with nitrogen thrice again, and heated to 80° C. for 3.5 h. The mixture is then diluted with ethyl acetate and washed with water thrice. The organic layer is dried over sodium sulfate and concentrated in vacuo. The residue is redissolved in DCM (1 mL) and trifluoroacetic acid (2 mL) is added. After 1 h, 4M aqueous NaOH is added and following extraction with DCM, the organic layer is dried over sodium sulfate and concentrated in vacuo. The residue is purified by silica gel flash chromatography (heptane-ethyl acetate, 1:1) to afford 2-(3-benzyloxy-phenyl)-6-chloro-1H-indole as a yellow solid. MS (ESI) m/z 335.07 (M+H)+.

1. customThe flask is evacuated
2. additionis added
3. customThe flask is evacuated
4. additionfilled with nitrogen thrice again
5. additionThe mixture is then diluted with ethyl acetate
6. washwashed with water thrice
7. dry with materialThe organic layer is dried over sodium sulfate
8. concentrationconcentrated in vacuo
9. dissolutionThe residue is redissolved in DCM (1 mL)
10. additiontrifluoroacetic acid (2 mL) is added
11. addition4M aqueous NaOH is added
12. extractionextraction with DCM
13. dry with materialthe organic layer is dried over sodium sulfate
14. concentrationconcentrated in vacuo
15. customThe residue is purified by silica gel flash chromatography (heptane-ethyl acetate, 1:1)