Toluene → (S)-Methyl 1-(1,3-benzodioxol-5-yl)-3-[4-methoxy-2-(phenylmethoxy)phenyl]-5-propoxy-1H-indene-2-carboxylate

Participants

Reaction Steps

A 500 mL three-necked round-bottomed flask under nitrogen was charged with (S)-Methyl-1-(1,3-benzodioxol-5-yl)-3-[(fluorosulfonyl)oxy]5-propoxy-1H-indene-2-carboxylate (10 g, 21.46 mmol), [4-methoxy-2-(phenylmethoxy)phenyl]boronic acid (Compound (u)) (5.53 g, 21.46 mmol), toluene (200 mL), EtOH (16 mL), and Pd(dppf)Cl2 catalyst (78.5 mg, 0.11 mmol). The mixture was stirred for 0.5 h at room temperature followed by the addition of K2CO3 solution (5.92 g in 16 mL H2O, 42.92 mmol) and heated to 70° C. for 45 min. The mixture was cooled to room temperature, washed with H2O (2×50 mL), brine (1×50 mL), dried over MgSO4 and the solvent removed in vacuo. The crude product was purified via recrystallization from 2-methoxy ethanol to afford (S)-Methyl 1-(1,3-benzodioxol-5-yl)-3-[4-methoxy-2-(phenylmethoxy)phenyl]-5-propoxy-1H-indene-2-carboxylate as a light yellow solid (8.7 g, 75% yield): mp 114.0-117.0° C. 1H NMR (DMSO, 335 K) δ 7.3-7.2 (m, 8 H), 7.1 (d, J=8.3 Hz, 1 H), 6.9 (dd, J=2.4, 8.2 Hz, 1 H), 6.85 (d, J=2.1 Hz, 1 H), 6.75 (dd, J=2.3, 8.2 Hz, 1 H), 6.65 (d, J=2.3 Hz, 1 H), 6.55 (d, J=1.5 Hz, 1 H), 5.9 (s, 2 H), 5.1 (s, 2 H), 4.9 (s, 1 H), 3.9-3.8 (m, 5 H), 3.4 (s, 3 H), 1.65 (quintet, J=7.8 Hz, 2 H), 0.9 (t, J=7.4 Hz, 3 H)

Provenance & Evidence