2,2,2-trifluoro-N-(pyridin-2-ylmethyl)acetamide → HCID 178431093, compound

Participants

Reaction Conditions

Reaction Steps

Following general procedure F using 2,2,2‐trifluoro‐N‐(pyridin‐2‐ylmethyl)acetamide (51.0 mg, 0.25 mmol), B2pin2 (95 mg, 0.375 mmol), [Ir(COD)OMe]2 (2.5 mg, 0.00375 mmol) and 1a (3.8 mg, 0.0075 mmol) in THF (1.25 mL). The reaction was stirred at 35 °C for 20 hours before cooling and the solvents removed. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 8.0:1:1 C4:C5‐borylation:SM in 69% yield. The crude product was unable to be purified by silica gel chromatography, however a small sample of the C4 product was isolated clean from flushing the silica with EtOAc (mixed fractions) followed by 20% MeOH in EtOAc (clean C4 fraction) as an off white solid (9.9 mg, 0.03 mmol, 12%):

Provenance & Evidence