HCID 46908774, compound → HCID 66746289, compound

Participants

Reaction Steps

N-(4-tert-butylbenzyl)-2-methyl-1,8-naphthyridine-3-carboxamide (150 mg, 0.45 mmol) was dissolved in THF (anh, 8.0 ml) under N2. Methylmagnesium bromide (4.5 ml of a 1M sln) was added dropwise. The mixture was stirred at r.t. for 2.0 h. The reaction was quenched with NH4Cl (sat). The product was extracted with EtOAc, dried (MgSO4), filtered and concentrated. The residue was dissolved in CHCl3 and O2 (94%) was bubbled through the solution for 3.0 h. The mixture was concentrated and purified by flash chromatography CH2Cl2/MeOH (96:4→95:5) yielding 50.0 mg of the title compound (32%). 1H NMR (CDCl3) δ 8.80 (m, 1H), 8.13 (m, 1H), 7.44 (d, 2H), 7.41 (d, 2H), 7.35 (m, 1H), 7.02 (t, 1H), 4.74 (d, 2H), 2.73 (s, 3H), 2.49 (s, 3H), 1.34 (s, 9H).

Provenance & Evidence