Cesium fluoride → {4-{2-[(3R)-1-Aza-bicyclo[2.2.2]oct-3-yloxy]-pyrimidin-5-yl}-2-nitro-phenyl}-carbamic Acid tert-butyl Ester

Participants

Reaction Steps

The product of Example 19A (0.57 g, 2.0 mmol) was coupled with the product of Example 34B (1.50 g, 4 mmol) under the catalysis of Pd2(dba)3 (24 mg, 0.025 mmol) and (tBu3P)2Pd (26 mg, 0.05 mmol) with CsF (Strem Chemicals, 1.80 g, 12.0 mmol) in dioxane (20 mL) and DMF (Aldrich, 2 mL) at 80° C. under N2 for 16 hours according to the procedure of Example 34C. The title compound was purified by chromatography (SiO2, EtOAc: MeOH (v. 2% NH3.H2O), 50:50, Rf. 0.3) as oil (590 mg, 67%). 1H NMR (300 MHz, MeOH-D4) δ 1.38 (s, 9 H), 1.46-1.59 (m, 1 H), 1.61-1.73 (m, 1 H), 1.74-1.88 (m, 1 H), 1.95-2.10 (m, 1 H), 2.22-2.33 (m, 1 H), 3.38-3.48 (m, 1 H), 5.15-5.25 (m, 1 H), 7.58 (d, J=8.2 Hz, 1 H), 7.97 (dd, J=8.8, 2.1 Hz, 1 H), 8.56 (d, J=4.9 Hz, 1 H), 8.97 (s, 2 H) ppm. MS (DCl/NH3): 442 (M+H)+.

Provenance & Evidence