Potassium Carbonate → 6-fluoro-5-[4-(3-hydroxyoxetan-3-yl)-3-methoxyphenyl]-1H-indole-3-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-2-methoxyphenyl]oxetan-3-ol (101 mg, 0.348 mmol) and 5-bromo-6-fluoro-1H-indole-3-carbaldehyde (88.5 mg, 0.365 mmol) in toluene/ethanol (8 mL, 3:1) was added 2N potassium carbonate (145 mg, 1.051 mmol) and Pd(dppf)Cl2 (30 mg, 0.041 mol). The reaction was degassed with N2 for 2 minutes. The reaction was heated to 110° C. for 3 hours. The reaction mixture was concentrated to give a crude residue, which was purified by column chromatography on a silica gel to afford the title compound (86 mg, 73%) as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 9.98 (s, 1H), 8.80 (br. s, 1H), 8.32 (d, 1H), 7.79 (d, 1H), 7.32 (d, 1H), 7.15 (m, 2H), 7.07 (s, 1H), 3.88 (s, 3H), 3.62 (s, 1H), 2.50 (m, 2H), 2.34 (m, 2H), 1.98 (m, 1H), 1.64 (m, 1H)

Provenance & Evidence