Triethylamine → 3-Methoxypyridine-2-carbonitrile

Participants

Reaction Steps

3-Methoxypyridine-1-oxide (25.2g, 209 mmol) was dissolved in acetonitrile (260 mL). Trimethylsilycyanide (66.35g, 669 mmol) and triethylamine (45.13g, 446 mmol) were added and the reaction mixture heated at reflux for overnight. The cooled solution was concentrated in vacuo to give a brown solid which was partitioned between CH2Cl2 and 3M Na2CO3. The organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by silica gel chomatography using 1:1 EtOAc/hexanes as eluent. Compound 762B was isolated (17.63g, 63%) as a light yellow solid. HPLC: 96.2% at 1,37 min(YMC S5 ODS column) eluting with 10–90% aqueous methanol containing 0.2% phosphoric acid over a 4 min gradient monitoring at 220 nm. MS (ES): m/z 134.88 [M+H]+.

Provenance & Evidence