2-broMo-6-nitrobenzonitrile

Intermediate 11: 2-Nitro-6-cyclopropylbenzonitrile; [0176] 2-Bromo-6-nitrobenzonitrile (0.56g), cyclopropyl boronic acid (0.63g), palladium (II) acetate (0.055g), tricyclohexylphosphine (0.135g) and potassium phosphate tribasic (2.36g) were dissolved in a mixture of toluene (15mL) and water (3mL). The mixture was heated at 100C under nitrogen for 18 hours. The mixture was cooled and then partitioned between water and DCM. The organic solution was separated, dried with magnesium sulfate, filtered and the solvent was removed under vacuum. The residue was purified by flash chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane. The fractions containing the desired product were combined and evaporated to give the title compound as a light yellow solid (0.5 lg).NMR (CDCI3) delta 8.05 (d, IH), 7.64 (t, IH), 7.27 (d, IH), 2.52-2.45 (m, IH), 1.33-1.26 (m, 2H), 0.91-0.85 (m, 2H)8.2 g of Intermediate 22: 2-Amino-6-bromobenzonitrile; [0189] 2-Bromo-6-nitrobenzonitrile (5g) was dissolved in a solution of methanol(lOOmL) and dioxane (65mL) and heated to reflux. Iron powder (4.6g) was added portion wise over 20 minutes and the mixture was heated at reflux for 4 hours. The mixture was allowed to cool to room temperature, filtered and the filtrate was evaporated under vacuum. The residue was triturated with water and the solid was collected by filtration to give the title compound as a light brown solid (3.8g).LCMS (Method E) r/t 3.01min (M+H) 197, 199

Molecular Weight:227.01
XLogP3:1.1
Hydrogen Bond Acceptor Count:3
Exact Mass:225.93779
Monoisotopic Mass:225.93779
Topological Polar Surface Area:69.6
Heavy Atom Count:12
Complexity:229
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes