Morpholine → HCID 11773517, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-bromo-naphthalene-2-carboxylic acid quinolin-7-ylamide, Example 32(b), (40 mg, 0.106 mmol) in dioxane (2 mL) was added tris(dibenzylideneacetone)dipalladium(0) (5 mg, Aldrich), biphenyl-2-yl-di-tert-butyl-phosphane (5 mg, Strem), morpholine (74 mg, 0.85 mmol, Aldrich) and lithium bis(trimethylsilyl)amide (0.53 ml of 1 M solution in THF, 0.53 mmol, Aldrich). The mixture was heated in microwave at 150° C. for 5 min, cooled to room temperature, and partitioned between satd NH4Cl (5 mL) and EtOAc (30 mL). The EtOAc layer was separated, washed with brine, dried over MgSO4, and filtered. The filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography (gradient, 5 to 10% (2 M NH3 in MeOH) in CH2Cl2) to provide the title compound as a yellow amorphous solid. MS (ESI, pos. ion) m/z: 384 (M+1).

Provenance & Evidence