Sodium Carbonate → (4-{4-[5-(6-Trifluoromethyl-pyridin-3-ylcarbamoyl)-pyridin-2-yl]-phenyl}-cyclohexyl)-acetic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To 200 mg (1 mmol) 6-Bromo-N-(6-trifluoromethyl-pyridin-3-yl)-nicotinamide, 217 mg (1 mmol) {4-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclohexyl}-acetic acid methyl ester in DME (20 mL), Dichloro[1,1′-bis(diphenylphosphino) ferrocene]palladium (II) dichloromethane adduct (37 mg, 5 mol %), and saturated sodium carbonate aqueous solution (2 mL) were added and the mixture stirred at 80° C. over night under N2. Evaporated to dryness and purified by passing over small plug of silica gel (30% ethyl acetate in hexanes) to afford (4-{4-[5-(6-Trifluoromethyl-pyridin-3-ylcarbamoyl)-pyridin-2-yl]-phenyl}-cyclohexyl)-acetic acid methyl ester: M+1=498.1. 1H NMR (400 MHz, DMSO-D6) ppm 1.06 (s, 4 H) 1.12-1.20 (m, 2 H) 1.45-1.57 (m, 2 H) 1.81 (d,J=8.59 Hz, 4 H) 2.25 (d, J=6.57 Hz, 2 H) 2.50-2.57 (m, 1 H) 3.60 (s, 2 H) 7.39 (d, J=8.34 Hz, 2 H) 7.94 (d,J=8.84 Hz, 1 H) 8.07-8.15 (m, 2 H) 8.35-8.43 (m, 1 H) 8.50 (d, J=8.59 Hz, 1 H) 9.10 (s, 1 H) 9.20 (d,J=2.02 Hz, 1 H).

Provenance & Evidence