Water → 3-(2-fluoropyridin-4-yl)-2-phenyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole

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Reaction Conditions

Reaction Steps

A mixture of 1.00 g (3.22 mmol) of 2-(phenyl)-3-iodo-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole, 1.80 g (8.06 mmol) of 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, 2.63 g (8.06 mmol) of Cs2CO3 and 526 mg (0.65 mmol) of Pd(dppf)Cl2 in 8 ml of THF is heated under argon at 60° C. for 16 h. 20 ml of water are added, and the reaction mixture is extracted with 3×50 ml of ethyl acetate. The combined organic phases are dried over MgSO4 and freed from the solvent under reduced pressure. Purification by column chromatography on silica gel (cyclohexane/ethyl acetate) gives 507 mg (57%) of the desired product; log P(HCOOH): 2.53; 1H-NMR (DMSO-d6): 8.10 (d, 1H), 7.40 (m, 5H), 7.07 (d, 1H), 6.85 (s, 1H), 4.19 (dd, 2H), 3.11 (dd, 2H), 2.62 (m, 2H).

Provenance & Evidence