Reaktion #1460046

Reaktionsgleichung

product

(3S)-3-[(5-bromopyrimidin-2-yl)oxy]quinuclidine

5-indolylboronic acid

NH3

→

5-{2-[(3S)-1-azabicyclo[2.2.2]oct-3-yloxy]pyrimidin-5-yl}-1H-indole

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe title product was purified by preparative HPLC (Gilson, column, Symmetry® C-8 7 μm, 40×100 mm
2. 2
   SonstigeEluting Solvent, MeCN/H2O (with 0.2% v. TFA) (v. 90/10 to 10/90 over 20 min.) Flow rate, 75 mL/min., uv, 250 nm) as solid (120 mg, yield, 38%)

Vorschrift

The product of Example 13E (283 mg, 1 mmol) was coupled with 5-indolylboronic acid (193 mg, 1.2 mmol) according to the procedure of Example 3A, The title product was purified by preparative HPLC (Gilson, column, Symmetry® C-8 7 μm, 40×100 mm. Eluting Solvent, MeCN/H2O (with 0.2% v. TFA) (v. 90/10 to 10/90 over 20 min.) Flow rate, 75 mL/min., uv, 250 nm) as solid (120 mg, yield, 38%). 1H NMR (300 MHz, CD3OD) δ 1.50–1.63 (m, 1H), 1.66–1.92 (m, 2H), 2.03–2.18 (m, 1H), 2.24–2.32 (m, 1H), 2.75–3.07 (m, 5H), 3.38–3.49 (m, 1H), 5.13–5.21 (m, 1H), 6.53 (dd, J=3.0, 0.7 Hz, 1H), 7.30 (d, J=3.4 Hz, 1H), 7.35 (dd, J=8.5, 1.7 Hz, 1H), 7.51 (dt, J=9.2, 0.7 Hz, 1H), 7.80 (dd, J=1.7, 0.7 Hz, 1H), 8.81 (s, 2H) ppm. MS (DCl/NH3): m/z 321 (M+H)+.

Quelle