Cesium carbonate → methyl 4-[3-[(E)-(4-tert-butylphenyl)methylideneamino]oxypropoxy]-2-[[(E)-3-(4-phenylphenyl)prop-2-enoyl]amino]benzoate

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Reaction Steps

The desired product was prepared using a procedure similar to Step 6 of example 34. Thus, 2-{[(2E)-3-(1,1′-biphenyl-4-yl)prop-2-enoyl]amino}-4-(3-bromopropoxy)benzoic acid methyl ester (0.299 g, 0.605 mmol) was reacted with cesium carbonate (0.414 g, 1.271 mmol) and 4-tert-butyl-benzaldehyde oxime (0.118 g, 0.665 mmol) in acetone (30 ml) to give 2-{[(2E)-3-(1,1′-biphenyl-4-yl)prop-2-enoyl]amino}-4-[3-({[(1E)-(4-tert-butylphenyl)methylidene]amino}oxy)propoxy]benzoic acid methyl ester (0.148 g, 0.251 mmol, 41%) as a pale yellow solid, mp 120-122° C. 1H NMR (DMSO-d6) δ 1.25 (s, 9H), 2.10-2.22 (m, 2H), 3.85 (s, 3H), 4.18 (t, 2H), 4.26 (t, 2H), 6.80 (dd, 1H), 6.95 (d, 1H), 7.37-7.54 (m, 7H), 7.62-7.78 (m, 5H), 7.83 (d, 2H), 7.97 (d, 1H), 8.22 (s, 1H), 8.30 (dd, 1H), 11.16 (s, 1H); mass spectrum [ES(−)], m/z 589 (M−H)−.

Provenance & Evidence