1-(3-BROMOPHENYL)PYRROLIDINE

Commercial 1, 3-dibromobenzene 1 (200.0mg, 0.85mmol), 12 pyrrolidine (60.5mg, 0.85mmol) and 157.0mg of a reagent constituted by 13 tris(dibenzylideneacetone)dipalladium(0), 14 BINAP and 15 t-BuONa (mol ratio: 0.05:0.15:2) were suspended in 16 toluene (2.5mL) and allowed to react in a sealed tube, at 80°C for 4.5h, under magnetic stirring. After cooling to room temperature, the mixture was filtered under reduced pressure and the resulting solution evaporated in vacuo. The residue was dissolved in CHCl1, 3-Dibromobenzene (1.0 g, 4.24 mmol), pyrrolidine (0.43 mL, 5.0 mmol), sodium tert-butoxide (1.14 g, 11.87mmol) and BINAP (0.2 g, 0.32 mmol) were dissolved in 17 mL of toluene. Pd2(dba)3 (0.097 g, 0.1 mmol) was addedthereto, and the mixture was stirred 4 hours under reflux. Solids were filtered through Celite and purified by columnchromatography to obtain the title compound (0.52 g, 54percent).1H-NMR (CDCl3) δ 7.05 (1H, t), 6.75 (1H, d), 6.67 (1H, m), 6.45 (1H, m), 3.26 (4H, m), 2.00 (4H, m)Synthesis of 1-(3-bromophenyl)pyrrolidine Synthesis of 1-3-bromophenyl)pyrrolidine To a solution of 1-bromo-3-fluorobenzene (250 mg, 1.429 mmol) in DMF (Volume: 5 mL) was added pyrrolidine (122 mg, 1.714 mmol) followed by K2C03 (395 mg, 2.86 mmol) and heated to 100 °C for 7 h. The reaction was diluted with 50 mL DCM and 50 mL water. The organic layer was separated, washed with water (2x20 mL), dried (MgSO4) and concentrated under reduced pressure. The crude product was purified by silica gel chromatography eluting with 10-50percent ethyl acetate:hexanes to afford the desired product 62 (226 mg, 1.000 mmol, 70percent yield). 1H NMR (500 MHz, CD3OD) : 7.02 (t, J= 8.0 Hz, 1H), 6.68 (dd, J= 8.0 Hz, J= 1.0 Hz, 1H), 6.65 (t, J= 2.0 Hz, 1H), 6.48 (dd, J= 8.5 Hz, J= 2.5 Hz, 1H), 3.23 (t, J= 6.5 Hz, 4H), 2.01 (quintet, J=3.5 Hz, 4H)Commercial 1, 3-dibromobenzene 1 (200.0mg, 0.85mmol), 12 pyrrolidine (60.5mg, 0.85mmol) and 157.0mg of a reagent constituted by 13 tris(dibenzylideneacetone)dipalladium(0), 14 BINAP and 15 t-BuONa (mol ratio: 0.05:0.15:2) were suspended in 16 toluene (2.5mL) and allowed to react in a sealed tube, at 80°C for 4.5h, under magnetic stirring. After cooling to room temperature, the mixture was filtered under reduced pressure and the resulting solution evaporated in vacuo. The residue was dissolved in CHCl1, 3-Dibromobenzene (1.0 g, 4.24 mmol), pyrrolidine (0.43 mL, 5.0 mmol), sodium tert-butoxide (1.14 g, 11.87mmol) and BINAP (0.2 g, 0.32 mmol) were dissolved in 17 mL of toluene. Pd2(dba)3 (0.097 g, 0.1 mmol) was addedthereto, and the mixture was stirred 4 hours under reflux. Solids were filtered through Celite and purified by columnchromatography to obtain the title compound (0.52 g, 54percent).1H-NMR (CDCl3) δ 7.05 (1H, t), 6.75 (1H, d), 6.67 (1H, m), 6.45 (1H, m), 3.26 (4H, m), 2.00 (4H, m)Synthesis of 1-(3-bromophenyl)pyrrolidine Synthesis of 1-3-bromophenyl)pyrrolidine To a solution of 1-bromo-3-fluorobenzene (250 mg, 1.429 mmol) in DMF (Volume: 5 mL) was added pyrrolidine (122 mg, 1.714 mmol) followed by K2C03 (395 mg, 2.86 mmol) and heated to 100 °C for 7 h. The reaction was diluted with 50 mL DCM and 50 mL water. The organic layer was separated, washed with water (2x20 mL), dried (MgSO4) and concentrated under reduced pressure. The crude product was purified by silica gel chromatography eluting with 10-50percent ethyl acetate:hexanes to afford the desired product 62 (226 mg, 1.000 mmol, 70percent yield). 1H NMR (500 MHz, CD3OD) : 7.02 (t, J= 8.0 Hz, 1H), 6.68 (dd, J= 8.0 Hz, J= 1.0 Hz, 1H), 6.65 (t, J= 2.0 Hz, 1H), 6.48 (dd, J= 8.5 Hz, J= 2.5 Hz, 1H), 3.23 (t, J= 6.5 Hz, 4H), 2.01 (quintet, J=3.5 Hz, 4H)

Molecular Weight:226.11
XLogP3:4.3
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:225.01531
Monoisotopic Mass:225.01531
Topological Polar Surface Area:3.2
Heavy Atom Count:12
Complexity:143
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes