Dimethylformamide → HCID 11177047, compound

Participants

Reaction Steps

The product from Step 2 (80 mg, 0.30 mmol) was suspended in CH2Cl2 (3 mL) under Argon. DMF (20 μL) was added, followed by oxalyl chloride (27 μL, 0.30 mmol). This mixture was stirred at room temperature for 30 min, and the resultant yellow solution was added to a solution of 6-fluoro-1H-indazol-5-amine (50 mg, 0.33 mmol) in pyridine (3 mL) at −15° C. under Ar. After the reaction was stirred at −15° C. for 15 min, the reaction mixture was allowed to warm to room temperature over 1 h. The mixture was then poured into EtOAc (50 mL), washed sequentially with aq. NH4Cl (20 mL), NaOH (10 mL, 2.5 N), HCl (10 mL, 1.0 N) and brine. The organic phase was dried over Na2SO4, filtered and concentrated. The residue was triturated with 10% EtOAc/10% ether/80% hexanes to afford the title compound (78 mg, 65%). MS (ES+) m/e 401 [M+H]+.

Provenance & Evidence