4-Bromo-1H-indole-2-carbonitrile

Phosphorous oxychloride (1.9 mL, 20 mmol) was added to a suspension of 4-bromo- lH-indole-2-carboxylic acid amide (1.32 g, 5.5 mmol.) in toluene (10 mL) and the mixture was stirred at reflux for 45 min. On cooling, the mixture was poured into an aqueous NaReference Example 16; 4-Bromo-lReference Example 18; 4-Bromo-lJy-indoIe-2-carbonitrile; Phosphorous oxychloride (1.9 mL, 20 mmol) was added to a suspension of 4-bromo- lH-indole-2-carboxylic acid amide (1.32 g, 5.5 mmol.) in toluene (10 mL) and the mixture was stirred at reflux for 45 min. On cooling, the mixture was poured into an aqueous NaIntermediate 116: 4-Bromo-lH-indole-2-carbonitrile (0799) To a solution of 4-bromo-l indole-2-carboxamide (207.3 mg, 0.87 mmol) in ethyl acetate (8 mL) in a microwave vial was added 2, 4, 6-tripropyl-l, 3, 5, 2, 4, 6-trioxatriphosphinane 2, 4, 6-trioxide (50percent in ethyl acetate, 0.630 mL, 1.06 mmol). The vial was sealed and the mixture stirred in a microwave reactor at 100 °C for 1.5 h. The vial was resealed and the mixture stirred in a microwave reactor at 100 °C for a further total of 2 h. Further 2, 4, 6-tripropyl-l, 3, 5, 2, 4, 6-trioxatriphosphinane 2, 4, 6-trioxide (50percent in ethyl acetate, 0.250 mL, 0.42 mmol) was added, the vial resealed and the mixture stirred in a microwave reactor at 100 °C for a further 3.5 h. To the reaction mixture was added water (10 mL) and the layers separated. The aqueous layer was extracted with further ethyl acetate (2 x 10 mL) and the organic layers combined and filtered through a cartridge fitted with a hydrophobic frit. The filtrate was evaporated in vacuo to give a light yellow crystalline solid. This was redissolved in DMSO (2 mL) and directly purified by MDAP (high pH). The required fractions were evaporated under a stream of nitrogen, redissolved in methanol (approx. 2 mL each) and combined. This solution was evaporated under a stream of nitrogen and the residue dried in vacuo to give the desired product 4-bromo-l/ indole-2-carbonitrile (145.0 mg, 0.66 mmol, 76 percent yield) as a glassy white solid. (0800) LCMS (2 min High pH): Rt = 1.14 min, [M-H]- = 219.0.

Molecular Weight:221.05
XLogP3:2.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:219.96361
Monoisotopic Mass:219.96361
Topological Polar Surface Area:39.6
Heavy Atom Count:12
Complexity:220
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes