Bis(trimethylsilyl)carbodiimide → N-(5-(3-cyanophenyl)-2',3',5',6'-tetrahydrospiro[indene-2,4'-pyran]-3(1H)-ylidene)cyanamide

Participants

Reaction Steps

To a solution of 3-(1-oxo-1,2′,3,3′,5′,6′-hexahydrospiro[indene-2,4′-pyran]-6-yl)benzonitrile (42 mg, 0.139 mmol) in anhydrous DCM (10 mL) under N2 atmosphere was added 1 M TiCl4 (in DCM, 0.28 mL, 0.28 mmol) dropwise within 15 min at room temperature. It was stirred another 1 h after the addition. To this mixture was added Bis-trimethylsilylcarbodiimide (0.1 mL, 0.427 mmol) dropwise. The resulting mixture was stirred overnight. The reaction mixture was quenched with ice-water (20 g), and stirred for 20 min, then it was transferred to a separating funnel, the separated aqueous phase was extracted 2 times with DCM. The combined organic phases were dried over anhydrous Na2SO4, and filtered, and concentrated to give 44 mg of N-(5-(3-cyanophenyl)-2′,3′,5′,6′-tetrahydrospiro[indene-2,4′-pyran]-3(1H)-ylidene)cyanamide as light brown solid which was used for next step without further purification. MS ESI+ve m/z 328 (M+H)+.

Provenance & Evidence