Dimethylamine → 6-Bromo-1-cyanomethyl-1H-indole-3-carboxylic Acid Dimethylamide

Participants

Reaction Steps

In a reaction tube was added 26 mg (94 micromol) of 6-bromo-1-cyanomethyl-1H-indole-3-carboxylic acid, 138 mg (approximately 186 micromol of carbodiimide functionality) of polystyrene carbodiimide resin (Argonaut Technologies, Foster City Calif., Product No. 800371), 21.3 mg (158 micromol) of HOBT (hydroxybenzotriazole), 1.5 mL dichloromethane, and 3 drops of DMF. The tube was capped, swirled and allowed to shake on a mechanical shaker for 1 hour at room temperature. The cap was removed, and dimethylamine (1 equivalent, 78 micromol) was added to the tube. The tube was re-capped and shaken for 24 hours at room temperature. 200 microliters of DMF was then added to the tube, and the tube was re-capped and shaken for an additional 48 hours, after which 130 mg (230 micromol) of polystyrene isocyanate resin (Argonaut Technologies, Foster City Calif., Product No. 800260) was added, followed by 1 hour of shaking, to remove excess dimethylamine. The content of the tube was filtered through a Varian liquid extraction tube (pre-washed with 20 microliters of saturated sodium bicarbonate solution), and washed 3× with 1 mL dichloromethane. The combined organic fractions were evaporated under reduced pressure to yield 6-Bromo-1-cyanomethyl-1H-indole-3-carboxylic acid dimethylamide as an oil. Step 4

Provenance & Evidence