Carbon tetrabromide → HCID 118035439, compound

Participants

Reaction Steps

To di-tert-butyl malonate (0.207 mL, 0.925 mmol), THF (40 mL) and DBU (0.139 mL, 0.925) were added, and the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was cooled to −20° C., and carbon tetrabromide (207 mg, 0.925 mmol) was added thereto, and the resulting mixture was stirred at −20° C. for 2 hours. To the reaction mixture, a saturated aqueous ammonium chloride solution was added, and the resulting mixture was extracted with chloroform. The organic layer was dried over sodium sulfate, and the solvent was evaporated under reduced pressure. To a portion (80 mg) of the obtained residue, DMF (1.43 mL), Compound 8 (12.5 mg, 0.029 mmol), and potassium carbonate (11.9 mg, 0.086 mmol) were added, and the resulting mixture was stirred at room temperature for 2 hours. To the reaction mixture, a saturated aqueous ammonium chloride solution was added, and the resulting mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by thin-layer chromatography (ethyl acetate/n-hexane=1/9). By using the obtained residue, Compound 22 (1.1 mg) was obtained in the same manner as Step 2 of Example 7.

Provenance & Evidence