2,2,2-trifluoro-N-(pyridin-2-ylmethyl)acetamide → HCID 178431065, 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 dtbpy (2.0 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 30:30:16:9 C4:C5:C3,5‐borylation:SM in 60% yield. The crude product was unable to be purified by silica gel chromatography and was hence characterised from the crude. By subtracting the resonances for the C4 isomer, SM, and using a combination of 2D NMR analysis the NMR data of the C5 and C3,5 isomers can be assigned as follows:

Provenance & Evidence