Water → HCID 68675381, compound

Participants

Reaction Steps

A solution of 2-methyl-4-(2-fluorobenzyloxy)-1-benzofuran-6-carboxylic acid (Method 3; 0.60 mg, 0.2 mmol) and methyl 2-aminopyridine-5-carboxylate (61 mg, 0.4 mmol, 2 eq) in pyridine (1 ml) was treated with phosphorus oxychloride (20.5 μl, 0.22 mmol, 1.1 eq), and the reaction mixture stirred for 16 hrs at ambient temperature. The reaction mixture was poured into water and extracted twice with ethyl acetate; the extracts were washed with brine, dried (MgSO4) and evaporated to give a yellow gum. This was chromatographed (10 g Bondelut, eluting with hexane containing ethyl acetate, 0-100%) to give the title compound as a solid (61 mg, 70%). NMR: 2.46 (s, 3H), 3.87 (s, 3H), 5.37 (s, 2H), 6.66 (s, 1H), 7.25 (m, 2H), 7.42 (m, 1H), 7.62 (m, 2H), 7.91 (s, 1H), 8.36 (m, 2H), 8.91 (s, 1H), 11.20 (bs, 1H); m/z 435 (M+H)+, 100% by LC-MS.

Provenance & Evidence