Ethyl Acetate → 3-(Pyridin-4-ylamino)-1H-indole-2-carboxylic Acid Diethylcarbamoylmethyl Ester

Participants

Reaction Conditions

Reaction Steps

Stir at 50° C. for 10 min. a mixture of 3-(4-pyridinylamino)-1H-indole-2-carboxylic acid (2.0 g, 8 mmol), KI (10 mg) and Cs2CO3 (2.8 g, 8.6 mmol) in DMF (125 mL). Allow to cool to ambient temperature and then cool in an ice bath. Add 2-chloro-N,N-diethylacetamide (1.077 g, 0.9 mmol) and allow to warm to ambient temperature. Add a brine solution to the reaction and extract with EtOAc (3×). Wash the extract with brine and water, dry (MgSO4), filter and concentrate under vacuum to give a semi-solid. Flash chromatograph over silica gel eluting first with EtOAc and 10% MeOH/EtOAc and obtain 0.317 g the title compound as a solid: MS 367(M+H); HPLC: Rt=4.75 min. (95/5/0.1 (A) 5/95/0.1 (B) Water/CAN/Formic Acid YMC ODS-A 2×50 mm 1 mL/min Gradient Composition: 100% A for 0.1 min Linear Gradient to 100% B at 2 min Hold until 3.5 min).

Provenance & Evidence