Sodium Carbonate → Ethyl 1-(2'-fluoro-2,3'-bipyridin-6-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of the title compound from Example 1 Step A (100 mg, 0.3 mmol), (2-fluoropyridin-3-yl)boronic acid (66 mg, 0.47 mmol), trans dichlorobis(triphenylphosphine) palladium (II) (31.0 mg, 0.05 mmol), Na2CO3 (0.47 mL, 2.0 M aqueous, 0.94 mmol) and acetonitrile (1 mL) in a nitrogen-filled capped vial was stirred at 100° C. After 50 min, the mixture was allowed to cool to ambient temperature, then was concentrated in vacuo. Purification by flash chromatography on silica gel using hexane:EtOAc (6:1 to 4:1 v/v) as mobile phase provided the title compound: LCMS m/z 381.1 [M+H]+; 1H NMR (400 MHz, CDCl3) δ 8.63 (m, 1H), 8.27 (m, 1H), 8.13 (s, 1H), 8.10 (d, J=7.9 Hz, 1H), 8.03 (t, J=7.9 Hz, 1H), 7.70 (d, J=7.8 Hz, 1H), 7.35 (m, 1H), 4.39 (q, J=7.1 Hz, 2H), 1.39 (t, J=7.1 Hz, 3H).

Provenance & Evidence