Tri-o-tolylphosphine → HCID 69431616, compound

Participants

Reaction Steps

The product of Example 28B (300 mg, 0.8 mmol) was coupled with the product of Example 28A (450 mg, 0.95 mmol) under the catalysis of Pd2(dba)3 (Aldrich, 30 mg, 0.033 mmol) and P(o-tolyl)3 (Aldrich, 30 mg, 0.1 mmol) in dry DMF (Aldrich, 4 mL) at 80° C. for 3 hours. It was then concentrated under reduced pressure and the free base of the title compound was purified by preparative HPLC (Xterra™, column, Xterra RP-18 5 μm, 30×100 mm. Eluting Solvent, MeCN/H2O(NH4HCO3, 0.1 M, pH=10) (v. 90/10 to 10/90 over 20 min.) Flow rate, 75 mL/min., uv, 250 nm) (60 mg, yield, 14%). The free base was treated with fumaric acid (Aldrich, 17 mg, 0.15 mmol) in EtOAc/MeOH (v.10:1, 5 mL) at ambient temperature for 10 hours to give the title compound (56 mg, 74%). 1H NMR (300 MHz, MeOH-D4) δ ppm 1.77-2.18 (m, 3H) 2.22-2.36 (m, 1H) 2.45-2.54 (m, 1H), 3.15-3.43 (m, 5H), 3.71-3.82 (m, J=14.9 Hz, 1H), 4.14-4.41 (m, 3H), 4.61-4.93 (m, 3H), 6.69 (s, 2H), 6.91-7.04 (m, 3H), 7.12-7.22 (m, J=8.8 Hz, 2H), 7.31-7.42 (m, 2H), 7.44-7.54 (m, 3H) ppm. MS (DCl/NH3) m/z 550 (M+H)+. Anal. Calculated for C28H28N3OI.1.15 C4H4O4: C, 57.33; H, 4.81; N, 6.15. Found: C, 57.13; H, 4.42; N, 6.22.

Provenance & Evidence