3-Chloro-4-fluoroaniline → HCID 44435431, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-chloro-4-fluorobenzenamine (550 mg, 3.78 mmol, 38 eq), 4-(cyclopentylamino)-6-fluoro-1,7-naphthyridine-3-carbonitrile (28 mg, 0.1 mmol, 1 eq), and cesium carbonate (506 mg, 1.55 mmol, 15.5 eq) in DMF (4 mL) was heated to 200° C. in a microwave tube for 1 hr using microwave reactor. Preparative HPLC purification yielded 15 mg product (36% yield): 1H NMR (400 MHz, DMSO-D6) δ ppm 1.52-1.68 (m, 2 H) 1.70-1.91 (m, 4 H) 1.99-2.16 (m, 2 H) 4.58-4.76 (m, 1 H) 7.33 (t, J=9.09 Hz, 1 H) 7.45-7.56 (m, 1 H) 7.76 (s, 1 H) 7.80 (d, J=7.07 Hz, 1 H) 7.87-7.97 (m, 1 H) 8.32 (s, 1 H) 8.90 (s, 1 H) 9.64 (s, 1 H).

Provenance & Evidence