Methyl iodide → Quinoline

Participants

Reaction Conditions

Reaction Steps

To a solution of 8-bromo-6-methanesulfonylmethyl-quinoline from Step 1 (1 eq.) in THF (0.2M) at 0° C., was added potassium t-butoxide (1.3 eq.) over 30 min. After 0.5 h at 0° C., MeI (1.6 eq.) was added and the reaction mixture was stirred at 0° C. for 2 h. A second portion of potassium t-butoxide (1.3 eq.) was added over 30 min, followed by MeI (1.6 eq.). The final mixture was stirred at rt for 2 h. The mixture was poured in saturated aqueous NH4Cl and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. The residue was vigorously stirred in Et2O and the title compound was isolated by filtration as a pale yellow solid.

Provenance & Evidence