(4-Bromophenyl)(pyrrolidin-1-yl)methanone

A General procedure: To a stirred solution of the amine (2 g) in dichloromethane was added pyridine (1.2 eq.) followed by dropwise addition of the acid chloride(1.2 eq.). After 1 hr, further dichloromethane (10 ml) was added, the solution then washed successively with saturated aqueous sodium hydrogen carbonate, hydrochloric acid (2 M), water, then dried and the solvent removed under reduced pressure to give the amide.[0171] To a stirred mixture of 4-bromobenzoic acid (2.00 g, 10.0 mol) and Et3N (3.03 g, 30.0 mmol) in DCM (30 mL) wasadded HATU (4.18 g, 11.0 mmol) at 30° C. After 15 mins, pyrrolidine (972 mg, 12.0 mmol) was added into the mixture, which was stirred at 30° C. for 16 hrs. After LCMS and TLC(PE:Et0Ac=2: 1) showed the reaction was complete, the mixturewas concentrated and purified by colunm chromatographyon silica gel (PE:EtOAc=l:0-20:1-10:1-5:1-3:1) to givethe title compound (2.20 g, yield: 86.9percent) as a white solid.General procedure: Constant current electrolyses were performed at 25°C, using an Amel Model 552 potentiostat equipped with an Amel Model 731 integrator. All the experiments were carried out in a divided glass cell separated through a porous glass plug filled up with a layer of gel (i.e., methyl cellulose 0.5percent vol dissolved in DMF-EtGeneral procedure: 4-Brorno2rnethyIbenzoyl chloride (1.24 g, 5.30 mmol) was added to asuspension of (1R, 5S8-?oxa-3.-azabicyclo[3.2.1]octane (0.50 g, 4.4 mmol) and triethylamine (2.51 ml, 17.99 mmoi) in DCM (10 mL) at ambient temperature. The reaction mixture was stirred at ambient temperature for 2 hours, then diluted with DCM (30 mL) and washed with brine (x 2). The combined organic layers were concentrated in vacuo and purified by silica chromatography, eluting with 20% EtOAc/hexanes to afford the title compound as a solid, Under air conditions, add magnetons to a dry, clean 25mL round bottom flask in sequence.N-Boc amide (194.5 mg, 0.5 mmol) represented by the formula IId, An amine represented by the formula IIIa (53.3 mg, 0.75 mmol), Then, 2.5 mL of toluene dried by molecular sieve was added, and the reaction was performed at 100 C for 24 hours.10 mL of water was added to quench the reaction, and extracted with dichloromethane (25 mL x 3 times), The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate.The filtrate was evaporated by rotary evaporation to remove the solvent. After concentration, 200-300 mesh silica gel column chromatography was performed.A mixed solvent of ethyl acetate and petroleum ether (1: 5) was rinsed.102 mg of the compound represented by the formula Id was isolated in a yield of 80%.

Molecular Weight:254.12
XLogP3:2.6
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:253.01023
Monoisotopic Mass:253.01023
Topological Polar Surface Area:20.3
Heavy Atom Count:14
Complexity:205
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes