Dimethyl Sulfate → HCID 67958038, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(6-isopropoxy-pyrazin-2-yl)-1H-indole-3-carboxylic acid (8.0 g, 26.9 mmol) in DMF (80 mL) was added K2CO3 (4.50 g, 32.3 mmol) and dimethyl sulfate (2.50 mL, 26.9 mmol) at RT and the reaction was heated to 80° C. for 3 h. The mixture was cooled to RT and partitioned between ice water (80 mL) and EtOAc (80 mL). The organic layer was separated and dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified with silica gel chromatography (eluting with 15% EtOAc in petroleum ether) to give methyl 5-(6-isopropoxypyrazin-2-yl)-1H-indole-3-carboxylate (6.5 g, 79%) as an off white solid. MS (ESI, pos. ion) m/z: 311.9 (M+1); 1H-NMR (DMSO-d6) δ ppm; 8.70 (d, J=1.6 Hz, 2H), 8.18 (s, 1H), 8.14 (s, 1H), 7.9 (dd, J=2.0 Hz, 1H), 7.62 (d, J=8.4, 1.6 Hz, 1H), 5.39-5.43 (m, 1H), 3.85 (s, 3H), 1.40 (d, J=6.0 Hz, 6H).

Provenance & Evidence