4-(3-BROMOPHENYL)MORPHOLINE

Intermediate 5: 3-Morpholin-4- lphenyl boronic acid1, 3-Dibromobenzene (50g, 0.21mol), morpholine (15.89mL, 0.19mol) and anhydrous toluene (200mL) were added to a flask by syringe under argon. The solution was thoroughly mixed before R-BINAP (1.32g, 0.0021mol) and ira(dibenzylideneacetone) palladium (0) (0.640g, 0.006mol) were added and finally DBU (25.8mL, 0.17mol) was added via syringe. The reaction mixture was stirred at 60°C. Sodium ie/t-butoxide (30.55 g, 0.32mol) was added and the reaction was heated to 100°C overnight. The suspension was diluted with ethyl acetate, filtered through Celite and washed with water and brine. The organic phase was dried (MgS0Intermediate 5: 3-Morpholin-4- lphenyl boronic acid1, 3-Dibromobenzene (50g, 0.212mol), morpholine (15.88mL, 0.191mol) and anhydrous toluene (200mL) were added to a flask by syringe under argon. The solution was thoroughly mixed before R-BINAP (1.32g, 0.0021mol) and iris (dibenzylideneacet one) palladium (0) (0.640g, 0.006mol) were added and finally DBU (25.83 mL, 0.1726) was added via syringe. The reaction mixture was stirred at 60°C. Sodium te/t-butoxide (30.55 g, 0.3178 mol) was added and the reaction was heated to 100°C overnight. The suspension was diluted with ethyl acetate, filtered through Celite and washed with water and brine. The organic phase was dried (MgS0To a solution of 3-bromoaniline (1.00 g, 5.81 mmol) in anhydrous DMF (20 mL) was added l-bromo-2-(2-bromoethoxy)ethane (1.62 g, 6.18 mmol) and DIPEA (2.25 g, 17.4 mmol). The solution was heated to 100 °C for 16 h, cooled and concentrated. The residue was purified by preparative HPLC purification. (230 mg, yield 16.4percent) MS (ESIExample 5 Example 5 Example 5

Molecular Weight:242.11
XLogP3:2.1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:241.01023
Monoisotopic Mass:241.01023
Topological Polar Surface Area:12.5
Heavy Atom Count:13
Complexity:159
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes