Methyl iodide → HCID 22462753, compound

Participants

Reaction Conditions

Reaction Steps

A 0° C. solution of 6-hydroxy-3-[3-methyl-4-(1-pyrrolidinylmethyl)benzyl]-2-[4-(1-methyl-5-oxopyrrolidin-2-ylcarbonylamino)phenyl]benzo[b]thiophene from Example 29, Part B (150 mg; 0.264 mmol) in 5 mL of dry DMF was treated with NaH (16 mg; 0.37 mmol). After 1 hr, methyl iodide (0.017 mL; 0.264 mmol) was quickly added via a syringe. The resulting mixture was stirred at 0° C. for 30 min, then it was allowed to warm to ambient temperature. The reaction mixture was poured into saturated aqueous NH4Cl and EtOAc (25 mL each). The aqueous layer was extracted with 5% MeOH/EtOAc (2×25 mL). The combined organics were dried over K2CO3, filtered and concentrated in vacuo. The crude residue was purified by radial chromatography (SiO2; gradient of 0.5% to 2% MeOH in CHCl3, saturated with NH4OH) afforded 37 mg (24%) of the title product as a yellow oil.

Provenance & Evidence