N-(1,1-Dimethylethyl)benzenamine → 5-{4-[(4-Tert-butylphenylamino)methyl]phenyl}-penta-2,4-dienoic acid

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Reaction Steps

Resin linked 5-(4-formylphenyl)penta-2,4-dienoic acid (50 mg) was suspended in NMP:DCP (2 ml, 1:1) for 30 min, then washed with DMF (3×2 ml). The solvent was removed, and a solution of tert-butylaniline (30 mg, 0.2 mmol) in DMF:TMOF (1.5 ml, 1:1) was added followed by HOAc (100 μl). The mixture was stirred at 2 hours at room temperature, before adding a solution of sodium cyanoborohydride (11 mg, 0.15 mmol) in DMF-MeOH (1 ml, 1:1). The mixture was stirred overnight at room temperature, then drained for solvent and washed with DMF (3×2 ml) and DCM (2 ml). A solution of 50% DIPEA in DCM (2 ml) was added and the resin was left stirring for 30 min. The resin was subsequently washed with DCM (3×2 ml), MeOH (1×2 ml) and DCP (2×2 ml).

Provenance & Evidence