2-(Dimethylamino)ethanol → 5-{[2-(Dimethylamino)ethyl]oxy}-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide

Participants

Reaction Conditions

Reaction Steps

A solution of DIAD (252 mg, 1.249 mmol) in toluene (1 ml) was added dropwise to a stirred solution of 5-hydroxy-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide (may be prepared as described in Example 29; 160 mg, 0.50 mmol), 2-(dimethylamino)ethanol (49.0 mg, 0.549 mmol) and Ph3P (328 mg, 1.25 mmol) in toluene (4 ml) under nitrogen at 0° C. The reaction mixture was stirred at 115° C. overnight. The mixture was then cooled and concentrated. The residue was added to water and extracted with ethyl acetate (3×60 ml). The organic phase was washed with saturated brine (30 ml), dried over sodium sulphate and evaporated in vacuo to give crude product. The crude product was added to a silica gel column (40 g) and was eluted with a 20:1 mixture of DCM/methanol (2 l) to yield the title compound as a yellow solid. 50 mg.

Provenance & Evidence