Water → 5-(4-Cyanomethyl-phenyl)-thiophene-2-sulfonic acid tert-butylamide

Participants

Reaction Conditions

Reaction Steps

5-Bromo-thiophene-2-sulfonic acid tert.-butylamide (0.6 g) was suspended in toluene (5 mL) under an Ar-atmosphere. To the suspension (4-cyanomethylphenyl)boronic acid (486 mg), Na2CO3 (533 mg), water (2.5 ml) and EtOH (2.5 mL) was added. To this suspension 2′-(dimethylamino)-2-biphenyl-palladium (II) chloride dinorbornylphosphine complex (23 mg) was added and the mixture was stirred for 18 h at 80° C. After that the suspension was cooled to 25° C., evaporated to ⅓ of the original volume and treated with EtOAc (30 mL). The organic layer was washed with aqueous HCl (1N, 10 mL) and brine. The organic layer was dried over Na2SO4, filtrated and evaporated to dryness. The crude material was purified by flash chromatography (eluent CH2Cl2, 2N NH3 in methanol) to yield 5-(4-cyanomethyl-phenyl)-thiophene-2-sulfonic acid tert-butylamide (268 mg, 40%) as a light yellow solid.

Provenance & Evidence