N-bromobutanimide → methyl 5-bromo-4-(tert-butoxycarbonyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]=[C:11]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[C:10]2[S:19][C:20]([C:22]([O:24][CH3:25])=[O:23])=[CH:21][C:9]1=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:33])C(=O)C1>C(Cl)Cl>[Br:33][C:12]1[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:9]2[CH:21]=[C:20]([C:22]([O:24][CH3:25])=[O:23])[S:19][C:10]=2[C:11]=1[CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution (0.1 M) of methyl 4-(tert-butoxycarbonyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate in DCM was cooled to 0° C. and treated with NBS (1.1 eq.) then it was left to warm to RT. The reaction was quenched with aqueous Na2S2O3 (saturated solution) and extracted with AcOEt. The organic phase was washed with aqueous Na2S2O3 (saturated solution) and brine then dried and concentrated, affording the title compound (98%) as a solid.