1H-Indole-4-boronic acid, pinacol ester → 4-{2-[(3R)-1-azabicyclo[2.2.2]oct-3-yloxy]pyrimidin-5-yl}-1H-indole

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Reaction Steps

The product of Example 11A (170 mg, 0.6 mmol) was coupled with 4-(4,4,5,5-tetra-methyl-[1,3,2]dioxaborolan-2-yl)-1H-indole ((ref. WO02055517, 146 mg, 0.6 mmol) according to the procedure in Example 8A. The title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.10) as a solid (76 mg, yield, 40%). 1H NMR (300 MHz, CD3OD) δ 1.50–1.64 (m, 1H), 1.67–1.93 (m, 2H), 2.05–2.19 (m, 1H), 2.25–2.33 (m, 1H), 2.73–3.12 (m, 5H), 3.39–3.50 (m, 1H), 5.17–5.25 (m, 1H), 6.55 (dd, J=3.4, 1.0 Hz, 1H), 7.11 (dd, J=7.1, 1.0, Hz, 1H), 7.23 (t, J=8.1 Hz, 1H), 7.35 (d, J=3.1 Hz, 1H), 7.44–7.49 (m, 1H), 8.85 (s, 2H) ppm. MS (DCl/NH3): m/z 321 (M+H)+.

Provenance & Evidence