BENZO[B]THIOPHENE-3-CARBONITRILE

White to light brown solid

General procedure: To a solution of an aromatic aldehyde 1 (0.500 mmol, 1.0 equiv) and TMSN3 (115 mg, 1.00 mmol, 2.0 equiv) in a premixed HFIP/ACN mixture (2.0 mL, 1:1) in a nitrogen-flushed two dram vial wasadded triflic acid (TfOH; 17.7 L, 0.200 mmol, 0.40 equiv) (exotherm and brisk effervescence due tonitrogen gas evolution was immediately observed). The vial was capped and the reaction mixture wasallowed to stir at rt for 20–75 min. The reaction mixture was concentrated under nitrogen. The residueobtained was suspended in CH2Cl2/hexanes mixture and loaded on a silica gel in a 5 g samplecartridge. Purification using a normal phase silica flash column on a CombiFlash purification systemafforded a corresponding aromatic nitrile 2 upon concentration of appropriate fractions.An oven dried screw cap test tube was charged with [NACN] (60 mg, [1.] 225 mmol), dried KI (34 mg, 0.205 mmol, 20 molpercent) and Cul (20 mg, 0.105 mmol, 10 molpercent), evacuated and backfilled with argon three times. 3-Bromo-benzo [b] thiophene [(135, UL, ] 1.032 mmol), N, N'-dimethylethylenediamine (110 [VLL, ] 1.033 mmol) and anhydrous toluene (700 [RL)] were added under argon. The tube was sealed and the reaction mixture was stirred magnetically at [110 °C] for 24 h. The resulting suspension was cooled to room temperature, 2 mL of ethyl acetate, [1] mL of ammonium hydroxide (30percent) and 1 mL of water were added. The mixture was stirred at [25 °C] for 10 min, then the organic layer was separated and the aqueous layer was extracted three times with ethyl acetate (3 x 2 mL). The combined organic layers were washed with 5 [ML] of water and dried over [MGS04.] The solvent was removed at reduced pressure. Purification of the residue by flash chromatography on silica gel (2 x 15 cm; hexane/ethyl acetate 10: 1) provided 122 mg (74percent yield) of the title compound as a pale yellow solid.An oven dried screw cap test tube was charged with [NACN] (60 mg, [1.] 225 mmol), dried KI (34 mg, 0.205 mmol, 20 mol%) and Cul (20 mg, 0.105 mmol, 10 mol%), evacuated and backfilled with argon three times. 3-Bromo-benzo [b] thiophene [(135, UL, ] 1.032 mmol), N, N'-dimethylethylenediamine (110 [VLL, ] 1.033 mmol) and anhydrous toluene (700 [RL)] were added under argon. The tube was sealed and the reaction mixture was stirred magnetically at [110 C] for 24 h. The resulting suspension was cooled to room temperature, 2 mL of ethyl acetate, [1] mL of ammonium hydroxide (30%) and 1 mL of water were added. The mixture was stirred at [25 C] for 10 min, then the organic layer was separated and the aqueous layer was extracted three times with ethyl acetate (3 x 2 mL). The combined organic layers were washed with 5 [ML] of water and dried over [MGS04.] The solvent was removed at reduced pressure. Purification of the residue by flash chromatography on silica gel (2 x 15 cm; hexane/ethyl acetate 10: 1) provided 122 mg (74% yield) of the title compound as a pale yellow solid.

Molecular Weight:159.21
XLogP3:2.8
Hydrogen Bond Acceptor Count:2
Exact Mass:159.01427034
Monoisotopic Mass:159.01427034
Topological Polar Surface Area:52
Heavy Atom Count:11
Complexity:193
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes