Tetrahydrofuran → Ammonium Hydroxide

Participants

Reaction Conditions

Reaction Steps

A 542 mg (2 mmol) sample of 5-bromo-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)-pyridine, from Example 28 above, was dissolved in 10 mL of THF, 6.6 mg of Ni(dppp)Cl was added, and the mixture was cooled to 0° C. To this solution was added 0.6 mL of methylmagnesium bromide, then the mixture was stirred at room temperature for 5 hours. The reaction was quenched by addition of NH4Cl solution, and the mixture was extracted with CHCl3. The organic extract was dried and concentrated. The residue was purified by chromatography on silica gel, eluting with 100:1.25:0.025 chloroform: methanol:ammonium hydroxide, to give 40 mg of the title compound. MS (DCI/NH3) m/e: 221 (M+H)+. 1H NMR (CDCl3,300 MHz) δ: 8.16 (d, J=2.4 Hz, 1H), 8.08 (d, J=1.2 Hz, 1H), 7.06 (t, J=2.4 Hz, 1H), 4.02 (dd, J=9.3, 5.4 Hz, 1H), 3.92 (dd, J=9.0, 6.0 Hz, 1H), 3.12 (m, 1H), 2.70-2.59 (m, 3H), 2.49 (s, 3H), 2.32 (m, 1H), 2.04 (m, 1H), 1.93-1.68 (m, 3H), 1.25 (t, J=7.80, 3H).

Provenance & Evidence