4-BROMO-3-CHLOROBENZONITRILE

off-white crystalline

To a stirred solution of 2-(4-(((1 , 4-dioxaspiro[4.5]decan-8-yl)methyl)sulfonyl)phenyl)- 4, 4, 5, 5-tetramethyl-1 , 3, 2-dioxaborolane Intermediate 6 (3.30 g, 7.81 mmol) in dioxane:water (3:1 , 40 ml_), sodium carbonate (2.48 g, 23.44 mmol), 4-bromo-3- chlorobenzonitrile (1.69 g 7.81 mmol) were added and the reaction mixture was degassed using argon for 20 min. Tetrakis[triphenylphosphine]palladium(0) (0.90 g, 0.78 mmol) was added to it and the reaction mixture was degassed for another 10 min and stirred at 100 C for 12 h in a sealed tube. The progress of the reaction was monitored by TLC [(TLC silica gel plate), 30% EtOAc in n-hexane]. After completion of the reaction, the reaction mixture was filtered through Celite and the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in EtOAc (100 ml.) and washed with water (50 ml_). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to get a crude residue. The residue obtained was purified by flash column chromatography (230-400 mesh silica gel, gradient 1-20% EtOAc in n- hexane) to afford the title compound Intermediate 20 (3.00 g, 89%) as white solid.Analytical data: LCMS (ESI) m/z = 432.20 [M+1]+.To a suspension of 4-bromo-3-chloro-benzonitrile (0.5 g, 2.31 mmol) and K2CO3 (0.32 g, 2.31 mmol) in dry DMF (10ml_) was added 4-ethoxy-piperidine (0.41 ml_, 2.31 mmol) and the mixture was stirred at 100C overnight under a nitrogen atmosphere. The solvent was evaporated and the resultant gum was dissolved in DCM and washed with water, dried and evaporated to give crude 3-chloro-4-(4-ethoxy-1-piperidyl)-benzonitrile, (0.55 g, 89%). (0828) m/z ES+ [M+H]+ 265To a solution of

Molecular Weight:216.46
XLogP3:3
Hydrogen Bond Acceptor Count:1
Exact Mass:214.91374
Monoisotopic Mass:214.91374
Topological Polar Surface Area:23.8
Heavy Atom Count:10
Complexity:162
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes