Sodium Carbonate → HCID 68841605, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-iodo-5-(trifluoromethyl)pyridin-2-amine (13 g, 45.1 mmole), 4-(triethylsilyl)but-3-in-1-ol (12.4 g, 67.7 mmole), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane (1.78 g, 2.26 mmole), lithium chloride (1.86 g, 45.1 mmole) and sodium carbonate (9.54 g, 90.3 mmole) in DMF (460 ml) was stirred under nitrogen for 15 hours at 100° C. The reaction mixture was cooled to RT, 2 l of EtOAc/ether (1:1) were added, and the mixture was poured into 2 l of H2O. The two-phase suspension was filtered through filter earth. After separating the phases the aqueous phase was extracted with EtOAc (2×1 l). The organic phases were combined and washed with H2O and with saturated NaCl solution and dried over MgSO4. After filtering the drying agent the solvents were removed on a rotary evaporator. The residue was purified by column chromatography (tert.-butyl methyl ether/n-hexane=2:3). The mixed fraction thereby obtained was taken up 4 times, each time with 20 ml of dichloromethane and suction filtered from the white crystalline solid. The first three fractionated precipitates were combined: 2-(2-(triethylsilyl)-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanol was obtained (3.8 g, 24.4%).

Provenance & Evidence