Triethylborane → Tert-butyl 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-6-ethylpyridin-2-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

tert-Butyl 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-6-chloropyridin-2-ylcarbamate (11-4, 0.496 g, 1.33 mmol) was dissolved in 2 mL DMF. Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (0.087 g, 0.11 mmol), cesium carbonate (2.601 g, 7.98 mmol), and triethylborane (1M in hexanes) (3.190 mL, 3.19 mmol) were added and the solution was heated to 50° C. After 24 hours the reaction was allowed to cool to room temperature and was concentrated to afford a brown oil. The oil was filtered through celite and washed with CH2Cl2. The filtrate was concentrated to afford a light brown oil. The oil was purified by flash column chromatography (10:90 EtOAc/hexanes) to afford tert-butyl 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-6-ethylpyridin-2-ylcarbamate as a light yellow oil. Free base: 1H NMR (CDCl3) δ 7.60 (s, 1H), 7.14 (bs, 1H), 6.91 (s, 1H), 4.71 (s, 2H), 2.68 (q, 2H, J=7.63 Hz), 1.51 (s, 9H), 1.25 (t, 3H, J=7.63 Hz), 0.95 (s, 9H), 0.10 (s, 6H).

Provenance & Evidence