Potassium Carbonate → methyl 5-(N-(5-iodo-3-(methylcarbamoyl)-2-p-tolylfuro[2,3-b]pyridin-6-yl)methylsulfonamido)pentanoate

Participants

Reaction Conditions

Reaction Steps

5-iodo-N-methyl-6-(methylsulfonamido)-2-p-tolylfuro[2,3-b]pyridine-3-carboxamide (100 mg, 0.206 mmol) was dissolved in dimethylacetamide (10 mL) and K2CO3 (39.9 mg, 0.288 mmol) was added then followed by methyl 5-bromopentanoate (0.059 mL, 0.412 mmol). The mixture was heated at 150° C. in the microwave for 20 min. Conversion approx 75% by LCMS, after which addition of additional methyl 5-bromopentanoate (3 eqs) and K2CO3 (2 eqs) did not result in additional conversion. Filtration and purification by HPLC (TFA/CH3CN/H2O) afforded 57 mg (0.095 mmol, 46%) methyl 5-(N-(5-iodo-3-(methylcarbamoyl)-2-p-tolylfuro[2,3-b]pyridin-6-yl)methylsulfonamido)pentanoate MS-ES [M+H]+=599.8, LC RT=1.61 min, Method A.

Provenance & Evidence