1-Methylpiperazine → 2-(4-N-Methylpiperazino)-3-(3,4,5-trimethoxybenzoyl)-6-methoxy-benzo[b]furan
Reaction equation
Br[C:2]1[O:6][C:5]2[CH:7]=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:4]=2[C:3]=1[C:13](=[O:26])[C:14]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=1.[CH3:27][N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>C(#N)C.ClCCl>[CH3:27][N:28]1[CH2:33][CH2:32][N:31]([C:2]2[O:6][C:5]3[CH:7]=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:4]=3[C:3]=2[C:13](=[O:26])[C:14]2[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=2)[CH2:30][CH2:29]1Participants
Procedure
To a stirred solution of 2-bromo-3-(3,4,5-trimethoxybenzoyl)-6-methoxy-benzo[b]furan (20 mg, 0.047 mmol) in a mixture of acetonitrile/dichloromethane; 1:1 (2 mL) was added N-methylpiperazine (50 μL, excess) and the reaction mixture was stirred at room temperature for 1 hour. After this time the solvent was removed by distillation under vacuum and the product was purified by PTLC (eluent=hexane/ethyl acetate; 4:6+1% triethylamine) to give the title compound as a green yellow paste which was crystallized by freeze drying in t-butanol to give a yellow solid; (8 mg, 43%); 1H NMR (300 MHz, CDCl3) δ 7.07(s, 2H, benzoyl Hs), 6.93(d, 1H, J=8.60 Hz), 6.84(d, 1H, J=2.25 Hz), 6.65(dd, 1H, J=8.64, 2.30 Hz), 3.92(s, 3H, OMe), 3.83(s, 6H, 2×OMe), 3.78(s, 3H, OMe), 3.66-3.64(bm, 4H), 2.65-2.63(bm, 4H), 2.40(s, 3H, N-Me); 13C NMR (75 MHz, CDCl3) δ 188.76(CO), 162.24, 155.88, 152.72, 149.06, 141.09, 135.36, 121.68, 119.64, 110.42, 106.11, 155.88, 95.63, 60.64, 55.88, 55.44, 53.88, 47.06, 45.29.
Workup
- customAfter this time the solvent was removed by distillation under vacuum
- customthe product was purified by PTLC (eluent=hexane/ethyl acetate; 4:6+1% triethylamine)
Sources & evidence
- ORD record
- ord-36ccd19e40234562868bb9ea616da272
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08278290B2
Reaction notes
Loading…