Potassium Carbonate → 3-(3-((6-Amino-1-naphthyl)oxy)propyl)-7-(2-methylphenyl)-1h-indole-2-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of EXAMPLE 563A (45 mg), o-tolylboronic acid (15.7 mg), K2CO3 (1 M, 0.17 ml) and bis(triphenylphosphine)palladium(II) dichloride (7.2 mg, 0.01 mmol) in a mixture of dimethoxyethane (2.2 ml), ethanol (0.6 ml) and water (0.9 ml) was heated at 160° C. in a microwave reactor (CEM Discover) for 10 minutes. The reaction mixture was acidified with a diluted trifluoroacetic acid methanol solution and concentrated. The residue was suspended in a mixture of DMSO and methanol (1:1) and filtered. The filtrate was purified by RP HPLC to provide the desired product. 1H NMR (400 MHz, DMSO-D6) δ 10.43 (s, 1 H), 8.08 (d, J=8.90 Hz, 1 H), 7.69 (d, J=6.75 Hz, 1 H), 7.31-7.34 (m, 2 H), 7.18-7.29 (m, 5 H), 7.02-7.11 (m, 5 H), 6.64 (d, J=7.67 Hz, 1 H), 4.15 (t, J=5.98 Hz, 2 H), 2.49-2.53 (m, 2 H), 2.17-2.25 (m, 2 H), 2.06 (s, 3 H).

Provenance & Evidence