Dimethylcarbamoyl Chloride → Ethyl 4-({1-[(dimethylamino)carbonyl]azetidin-3-yl}oxy)-2-methyl-1-benzofuran-6-carboxylate
Reaction equation
[NH:1]1[CH2:4][CH:3]([O:5][C:6]2[C:11]3[CH:12]=[C:13]([CH3:15])[O:14][C:10]=3[CH:9]=[C:8]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:7]=2)[CH2:2]1.[CH3:21][N:22]([CH3:26])[C:23](Cl)=[O:24]>C(Cl)Cl>[CH3:21][N:22]([CH3:26])[C:23]([N:1]1[CH2:4][CH:3]([O:5][C:6]2[C:11]3[CH:12]=[C:13]([CH3:15])[O:14][C:10]=3[CH:9]=[C:8]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:7]=2)[CH2:2]1)=[O:24]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of ethyl 4-(azetidin-3-yloxy)-2-methyl-1-benzofuran-6-carboxylate (200 mg, 0.73 mmol) in dissolved in DCM with containing TEA (0.4 mL, 2.9 mmol) was added dimethylcarbamic chloride (0.1 mL, 1.09 mmol). The mixture solution was stirred at room temperature for 2 hrs. The reaction was diluted with DCM, washed with NaHCO3, brine, dried over Na2SO4 and concentrated under reduced pressure. The product was purified via gradient silica gel chromatography using EtOAc/Hexanes (20/80 to 60/40) to provide the product (138 mg, 55%) as a colorless oil. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.36-1.54 (m, 3 H) 2.49 (s, 3 H) 2.88 (s, 6 H) 4.06-4.20 (m, 2 H) 4.33-4.53 (m, 4 H) 5.04-5.18 (m, 1 H) 6.52 (s, 1 H) 7.01 (s, 1 H) 7.80 (s, 1 H); MS (ESI, pos): 347.