2-Fluoro-4-iodopyridine-3-carbaldehyde → HCID 68058238, compound

Participants

Reaction Conditions

Reaction Steps

To a 15 mL pressure bottle was added 2-fluoro-4-iodonicotinaldehyde (530 mg, 2.112 mmol), (2,4,6-trifluorophenyl)hydrazine (359 mg, 2.215 mmol), DMAP (53 mg, 0.434 mmol), and anhydrous NMP (4 mL). The reaction mixture was flushed with argon, securely capped, and heated to 185° C. for 1.75 h. The reaction mixture was worked up according to the procedure described in Intermediate 69A and the product was purified by Biotage Silica gel chromatography using a 40 g Thompson Single Step™ silica cartridge with a linear gradient from 100% hexanes to 100% CH2Cl2 over 14 column volumes to give 133 mg (16.8%) of the title compound as a yellow solid. LC/MS (Condition B): ret. T=3.7 min, (M+H)+ 375.90 and 230 mg (27.6%) of the hydrazone intermediate as a pale yellow solid, LC/MS (Condition B): ret. T=3.7 min, (M+H)+ 395.90.

Provenance & Evidence