Sodium Azide → HCID 86590934, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of [3-(2-oxo-1,2-dihydro-indol-3-ylidene)-1,3-dihydro-isobenzofuran-1-yl]-acetic acid (200 mg, 0.65 mmol) in THF (8.0 ml) at room temperature was added 2.5M n-BuLi in hexane (272 μl), and the yellow-brown slurry was stirred for 10 minutes. After cooling to 0° C., 2.0M oxalyl chloride in CH2Cl2 (325 μl) was added. The clear orange solution was stirred for 25 minutes, and then sodium azide (51 mg, 0.78 mmol) in water (0.5 ml) was added, followed by addition of water (1 ml). After 20 minutes, the reaction was partitioned between dilute NaHCO3 aqueous solution and CH2Cl2. The CH2Cl2 layer was washed with brine and dried with anhydrous Na2SO4 to give a yellow solution. The solution was diluted with toluene (200 ml), and then rotary evaporated to 100 ml volume. The toluene solution was heated at 90° C. for 40 minutes, cooled to room temperature, and then rotary evaporated to give 3-(3-isocyanatomethyl-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one as a yellow oily solid (130 mg, 66%).

Provenance & Evidence