1-Butyne → HCID 69514008, compound

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The title compound was synthesized in analogy to 2-amino-5-chloro-3-prop-1-ynylbenzoic acid methyl ester (described in example S85) using 1-butyne (excess ca 3 ml), 2-amino-5-chloro-3-iodo-benzoic acid methyl ester (prepared as described in example S85) (430 mg, 1.38 mmol), copper (I) iodide (19 mg, 0.10 mmol) and bis(triphenyl-phosphine) palladium (II) chloride (71 mg, 0.10 mmol) in triethylamine (10 ml). The final compound was purified by flash column chromatography (9:1 cyclohexane:EtOAc) to give 2-amino-3-but-1-ynyl-5-chlorobenzoic acid methyl ester (120 mg, 37%) as a yellow oil. 1H NMR (CDCl3, 300 MHz): δ 7.76 (d, J=2.5 Hz, 1H), 7.35 (d, J=2.5 Hz, 1H), 6.37 (br s, 2H), 3.87 (s, 3H), 2.49 (q, J=7.5 Hz, 2H), 1.27 (t, J=7.5 Hz, 3H).

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