Bromide ion → HCID 86727405, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl-9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,5-dihydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-2(1H)-one (prepared from the corresponding bromide (Preparation #1, Step D) following similar procedure as describe in Example #109, Step B, 0.103 g, 0.3 mmol), tert-butyl 6-benzyl-4-(trifluoromethylsulfonyloxy)-5,6-dihydropyridine-1(2H)-carboxylate (0.253 g, 0.6 mmol), Pd(dppf)Cl2—CH2Cl2 complex (0.073 g, 0.09 mmol) and K2CO3 (0.124 g, 0.9 mmol) in 1,4-dioxane (2 mL) and water (0.5 mL) was heated at 90° C. for 10 h. The reaction was cooled to ambient temperature. The solvent was removed in vacuo and the residue was purified by PTLC (eluting with 50% EtOAc in petroleum ether) to give tert-butyl 6-benzyl-4-(1-methyl-2-oxo-1,2,3,5-tetrahydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-9-yl)-5,6-dihydropyridine-1(2H)-carboxylate (0.147 g, 99%). LC/MS (Table 1, Method 2) Rt=1.308 min; MS m/z: 489 [M+H]+.

Provenance & Evidence