N-bromobutanimide → methyl 5-bromo-4-(tert-butoxycarbonyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

HRID 505808Notes

Reaction equation

HRID 505808 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]1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 68471407methyl 4-(tert-butoxycarbonyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

Product 1

HCID 67298537methyl 5-bromo-4-(tert-butoxycarbonyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. waitit was left
  2. customThe reaction was quenched with aqueous Na2S2O3 (saturated solution)
  3. extractionextracted with AcOEt
  4. washThe organic phase was washed with aqueous Na2S2O3 (saturated solution) and brine
  5. customthen dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7db390e8e54745819e5c6987c0ccb94e
Source dataset
uspto-grants-2010_08
Patent number
US07781431B2

Reaction notes

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