Sodium hydride → HCID 178525771, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (1S,4S)-4-hydroxycyclohexanecarboxylic acid (2.14 g, 14.9 mmol) in DMA (10 mL) was added to a stirred suspension of NaH (1.32 g, 30.2 mmol) in DMA (15 mL) at 0° C. where it was stirred for 10 min. The suspension was taken off the cooling bath and 5-bromo-2-fluoropyridine (1.53 mL, 14.87 mmol, CAS 766-11-0) was added followed by DMA (10 mL). The reaction was heated at 100° C. for 2.5 h. The solvent was evaporated and DCM and 2M HCl were added, the phases separated and the aqueous phase was extracted with DCM (2×50 mL). The combined organics were dried over MgSO4, filtered and evaporated. The remaining crude was purified by flash chromatography using 5-75% EtOAc (1% HOAc) in heptane to afford the title compound (1.86 g, 42%) as solid.

Provenance & Evidence