Chloroiodomethane → HCID 57586427, compound

Participants

Reaction Conditions

Reaction Steps

A 500 mL round-bottomed flask was charged with methyl 6-methylnicotinate (3.0 g, 20 mmol), chloroiodomethane (7.1 ml, 97 mmol), and 50 mL of THF. After cooling to −78° C., a freshly prepared solution of LDA (1M in THF made from diisopropylamine (14 ml, 99 mmol) and BuLi (39 ml, 97 mmol)) was added drop-wise over 1.5 h. After that time, the reaction was quenched with a solution of 5 mL HOAc in 15 mL of THF. The mixture was warmed to rt and diluted with sat. aq. NaHCO3. The mixture was concentrated then portioned between EtOAc and water. The organic layer was separated, dried over MgSO4, filtered, and concentrated to give a brown oil. To this oil was added thiourea (1.5 g, 20 mmol), NaOAc (4.9 g, 60 mmol) and 30 mL of EtOH. The mixture was heated at 80° C. for 15 min then cooled to rt. The mixture was concentrated in vacuo then diluted with water and EtOAc. The layers were separated and the organics were dried (MgSO4), filtered and concentrated to give an oil. Purification by MPLC (80 g, 10-100% EA/Hex) gave 4-(6-methylpyridin-3-yl)thiazol-2-amine as a yellow solid.

Provenance & Evidence