4-[2-(4-Bromophenyl)ethyl]morpholine

To a mixture of lithium aluminum hydride (3.35 g, 88.16 mmol, 2.00 equiv) in tetrahydrofuran (100 mL) maintained under nitrogen at -30°C was added a solution of 2-(4-bromophenyl)-l-morpholinoethanone (12.5 g, 44.17 mmol, 1.00 equiv) in tetrahydrofuran (30 mL) dropwise with stirring. The reaction mixture was stirred at - 30°C for 30 min and then at room temperature for 2 h. The reaction was then quenched sequentially by the addition of 3.5 mL of water, 10 mL of 15percent aqueous sodium hydroxide solution and 3.5 mL of water. The solid was removed by filtration. The filtrate was extracted with 1x150 mL of ethyl acetate. The organic layer was collected then washed with 2x30 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give 11.5 g (97percent) of 4- (4- bromophenethyl)morpholine as a white solid. LC-MS: (ES, m/z): 311 [M+CHTo a mixture of lithium aluminum hydride (3.35 g, 88.16 mmol, 2.00 equiv) in tetrahydrofuran (100 mL) maintained under nitrogen at −30° C. was added a solution of 2-(4-bromophenyl)-1-morpholinoethanone (12.5 g, 44.17 mmol, 1.00 equiv) in tetrahydrofuran (30 mL) dropwise with stirring. The reaction mixture was stirred at −30° C. for 30 min and then at room temperature for 2 h. The reaction was then quenched sequentially by the addition of 3.5 mL of water, 10 mL of 15percent aqueous sodium hydroxide solution and 3.5 mL of water. The solid was removed by filtration. The filtrate was extracted with 1×150 mL of ethyl acetate. The organic layer was collected then washed with 2×30 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give 11.5 g (97percent) of 4-(4-bromophenethyl)morpholine as a white solid. LC-MS: (ES, m/z): 311 [M+CHA mixture of morpholine (87 mg, 1.0 mmol) and 2-(4-bromophenyl)acetaldehyde (200 mg, 1.0 mmol) was stirred in dry CH2Cl2 (10 mL) for 10 min. Sodium triacetoxyborohydride (211mg, 1.0 mmol) was then added and the reaction mixture was stirred at room temperature for 1 h, then it was washed with saturated sodium bicarbonate solution (10 mL), dried (Na2SO4)and concentrated in vacuo. Purification of the crude product on a silica column eluting with5% [7 M NH3 in MeOH] in ethyl acetate afforded the desired product (188 mg, 70%);General procedure: The boronic acid pinacol ester (1 equiv.), aryl halide (1 equiv.) and Pd(dppf)Cl2·CH2Cl2 adduct (0.1 equiv.) were dissolved in a mixture of DME and aqueous sodium carbonate (1M) in a microwave vial. The vial was sealed, evacuated and backfilled with N2. The reaction mixture was heated in the microwave at 120C for 45min and monitored by LCMS. The reaction mixture was concentrated in vacuo to give the crude material which was purified by Biotage column chromatography (see individual compounds for details of the eluent used).A 1, 4-dioxane (1.8 mL) suspension of the compound (90 mg) obtained in Reference Example P-D08,

Molecular Weight:270.17
XLogP3:2.5
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:269.04153
Monoisotopic Mass:269.04153
Topological Polar Surface Area:12.5
Heavy Atom Count:15
Complexity:175
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes