2,6-Dichloro-4-iodobenzenamine → HCID 59436035, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 6-chloro-10-ethoxypyrido[4,3-c]-1,6-naphthyridine (Example 133, Step 3) (200 mg, 0.770 mmol) and 6,10-dichloropyrido[4,3-c]-1,6-naphthyridine (Example 133, Step 3)(193, 0.770 mmol) in THF (12 mL) were added 2,6-dichloro-4-iodoaniline (443 mg, 1.54 mmol) and sodium tert-butoxide (444 mg, 4.62 mmol) and the mixture was heated to 85° C. for 1 hr. After cooling to room temperature, the mixture was extracted with EtOAc. The organic layers were dried with MgSO4, filtered, and concentrated under reduced pressure. Column chromatography (100% hexane to 100% EtOAc) provided 10-chloro-N-(2,6-dichloro-4-iodophenyl)pyrido[4,3-c]-1,6-naphthyridin-6-amine and N-(2,6-dichloro-4-iodophenyl)-10-ethoxypyrido[4,3-c]-1,6-naphthyridin-6-amine. Most instances 10-chloro-N-(2,6-dichloro-4-iodophenyl)pyrido[4,3-c]-1,6-naphthyridin-6-amine and N-(2,6-dichloro-4-iodophenyl)-10-ethoxypyrido[4,3-c]-1,6-naphthyridin-6-amine were carried on as a mixture, however, the mixtures can be separated and carried on separately. This mixture (282 mg) was taken up in methanol (5 mL) and 25% sodium methoxide (3 mL) and heated at 100° C. for 1 hr. After cooling to room temperature, the solution was concentrated and then taken up in EtOAc and washed with water. The organic layers were dried with MgSO4, filtered, and concentrated to afford the title compounds.

Provenance & Evidence