反应详情

To a solution of benzo[d]oxazole-5-carbonitrile (CAS #:132227-01-1) (0.996 g, 6.91 mmol) in THF (20 mL), TMPMgCl.LiCl (1 M in THF) (6.91 mL, 6.91 mmol) was added at −78° C. After stirring for 30 min, tert-butyl 4-formyl-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 19-D) (1.00 g, 3.46 mmol) was added at −78° C. Then, the reaction mixture was warmed to rt. After stirring for 10 min, the reaction was heated at 50° C. After stirring for 1.5 h, the reaction mixture was cooled to rt, and diluted with aq. NH4Cl and brine. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with a 1:1 solution of 1M aq. NaHSO4 and brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by flash column chromatography on silica gel (heptane/EtOAc=100:0 to 40:60) to give the title compound. MS (ESI) m/z 432.3 (MH).

1. stirringAfter stirring for 10 min
2. temperaturethe reaction was heated at 50° C
3. stirringAfter stirring for 1.5 h
4. temperaturethe reaction mixture was cooled to rt
5. customThe layers were separated
6. extractionthe aqueous layer was extracted with EtOAc
7. washThe combined organic layers were washed with a 1:1 solution of 1M aq. NaHSO4 and brine
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated
11. customThe residue was purified by flash column chromatography on silica gel (heptane/EtOAc=100:0 to 40:60)