3-(4-Bromophenyl)-1-methylpyrrolidine

Uses

3-(4-Bromophenyl)-1-Methylpyrrolidine (cas# 1088410-99-4) is a useful reagent for the preparation of pyrazolopyrimidines for treatment and prevention of ALK2-mediated diseases.

Synthesis

The general procedure for the synthesis of 3-(4-bromophenyl)-1-methylpyrrolidine from formaldehyde and the compound (CAS:328546-98-1) was as follows: referring to the method of Example 11, formalin (0.0452 mL, 0.557 mmol), acetic acid (0.0319 mL, 0.557 mmol) and triacetoxyborohydride (118 mg , 0.557 mmol) were added to a chloroform-ethanol (3:1, 2 mL) solvent mixture containing 3-(4-bromophenyl)pyrrolidine (42 mg, 0.186 mmol). The reaction mixture was stirred at room temperature for 40 min. After completion of the reaction, the reaction solution was diluted with ethyl acetate and the diluted solution was washed with 10% aqueous sodium bicarbonate. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 43 mg of the title compound in 97% yield. The product was analyzed by mass spectrometry (GC) at m/z 239 [M]+, 1H-NMR (400 MHz, CDCl3) δ: 1.71-1.88 (1H, m), 2.29-2.50 (5H, m), 2.61-2.69 (1H, m), 2.72-2.80 (1H, m), 2.94-3.00 (1H, m), 3.28 -3.38 (1H, m), 7.15 (2H, d, J = 8.3 Hz), 7.40 (2H, d, J = 8.3 Hz).

References

[1] Patent: EP2166015, 2010, A1. Location in patent: Page/Page column 28