Methyl iodide → HCID 11567441, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of diisopropylamine (55.0 ml, 0.39 mmol) in THF (3 ml) at 0° C. was added nBuLi (2.5M, hex., 135 ml) slowly. After 20 minutes the mixture was cooled to −78° C. and (−)-4-(5-{(1R)-1-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]ethoxy}-4-methyl-4H-1,2,4-triazol-3-yl)pyridine (107 mg, 0.28 mmol) in THF (2 ml) was added. The resulting mixture was stirred for 45 minutes before CH3I (22 ml, 0.34 mmol) was added and the reaction mixture was stirred for 1 h at r.t. Sat. NH4Cl solution was added and the mixture was extracted with EA. The organic phase was washed with H2O and brine, dried and evaporated. Purification of the residue by silica gel chromatography using CHCl3:MeOH 50:1 followed by prep. HPLC gave the title compound (22 mg, 20%). 1H-NMR: 2.11 (s, 6 H) 3.63 (s, 3 H) 7.45 (d, 1 H) 7.52-7.57 (m, 1 H) 7.59 (d, 2 H) 7.98 (d, 1 H) 8.09 (s, 1 H) 8.72 (d, 2 H)

Provenance & Evidence