Methyl chloroformate → HCID 57731438, compound

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Reaction Steps

Methyl chloroformate (0.88 ml, 11.4 mmol) was added to a solution of 2-amino-5-iodo-benzoic acid (2.50 g, 9.5 mmol) and di-iso-propyl ethyl amine (5.96 ml, 34.4 mmol) in dichloromethane (50 ml) and the resulting mixture stirred at room temperature for 4 hours. The solvent was evaporated and the residue used without further purification. MS: m/z 322.1 (M+H+). To this crude was added tetrahydrofuran/acetonitrile/50% w/v potassium carbonate (80 ml), 3-(2-methoxy-phenyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (4.80 g, 9.5 mmol). This mixture was degassed with nitrogen, split into 4 portions and irradiated in the microwave to 150° C. for 30 min. The reaction mixtures were then combined and extracted with ethyl acetate (3×), dried over magnesium sulfate, and purified by silica gel chromatography to produce 2-methoxycarbonylamino-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-benzoic acid as a white solid. (2.51 g, 46%). MS: m/z 572.6 (M+H+).

Provenance & Evidence