Benzophenone imine → 6-amino-N-(4-tert-butylbenzyl)-2-methyl-1,8-naphthyridine-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

9.2 mg (0.01 mmol) Pd2 dba3 and 19 mg (0.03 mmol) BINAP were added to a degassed mixture of 205 mg (0.5 mmol) 6-bromo-N-(4-tert-butylbenzyl)-2-methyl-1,8-naphthyridine-3-carboxamide, 100 ml (0.6 mmol) diphenylmethanimine and 79 mg (0.7 mmol) KOtBu in 2 ml toluene. The flask was sealed with a septa and heated at 80° C. over night. The reaction mixture was diluted with EtOAc and filtered through celite and SiO2 with EtOAc. The filtrate was concentrated and treated with THF and 1.0 M HCl for 2 h. The solution was diluted with 0.5 M Hcl and washed with EtOAc/Pet. ether 1:1. The aqueous phase was neutralized with 1 M NaOH and extracted twice with CH2Cl2. The organic phase was dried (MgSO4) and concentrated. Flash chromatography (CH2Cl2/MeOH 10:1) gave 4.6 mg of the title compound.

Provenance & Evidence