Sodium hydride → HCID 67067770, compound

Participants

Reaction Steps

Sodium hydride (60% dispersion in mineral oil, 1.27 g, 31.66 mmol) was added to anhydrous THF (100 mL) with stirring under an atmosphere of nitrogen. After 5 min, a solution of 7-methoxy-1H-indazole-6-carboxylic acid methyl ester (5.44 g, 26.38 mmol, prepared as described in J. Med. Chem. 2006, 49, 4762-4766) in anhydrous THF (50 mL) was added dropwise over 15 min. After stirring for 30 min, a solution of dimethylsulfamoyl chloride (3.68 mL, 34.3 mmol) in anhydrous THF (20 mL) was added dropwise over 10 min. After stirring for 2 h, the reaction mixture was quenched by addition of water (50 mL) and transferred to a separating funnel using EtOAc. The organic layer was washed with water. The aqueous layers were combined and extracted using EtOAc. The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 0 to 20% EtOAc in DCM) to afford the title compound as a yellow solid (6.23 g, 75%). 1H NMR (400 MHz, DMSO-d6): δ 8.98 (s, 1H), 7.47 (d, J=8.8 Hz, 1H), 7.33 (d, J=8.8 Hz, 1H), 4.29 (s, 3H), 3.85 (s, 3H), 2.97 (s, 6H).

Provenance & Evidence