Sodium Carbonate → (rac)-2-(1-{[1-(2,2,2-Trifluoro-acetylamino)-cyclopropanecarbonyl]-amino}-indan-5-yl)-benzoic acid methyl ester

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Reaction Conditions

Reaction Steps

1-(2,2,2-Trifluoro-acetylamino)-cyclopropanecarboxylic acid ((rac)-5-bromo-indan-1-yl)-amide (intermediate A-1 [B]) (0.20 g, 511 μmol) and 2-(methoxycarbonyl)phenylboronic acid (184 mg, 1.02 mmol) were dissolved in dioxane (9.0 ml); then, sodium carbonate (163 mg, 1.53 mmol), dissolved in water, was added while stirring. Subsequently, (1,1′-bis-diphenylphosphino)-ferrocene)palladium-(II)dichloride (1:1 complex with CH2Cl2) (18.7 mg, 25.6 μmol, eq: 0.05) was added and the reaction mixture was heated up to 50° C. for 5 hours. It was then poured into H2O (50 ml) and extracted with EtOAc (2×25 mL). The organic layers were dried over MgSO4, filtered and concentrated in vacuo to give a crude product (0.296 g) which was purified by flash chromatography (silica gel, 20 g, 0% to 2% MeOH in CH2Cl2) to yield the title compound (0.21 g, 91%) as light brown oil. MS: 445.1 (M−H−).

Provenance & Evidence