Trifluoroacetic acid → methyl 5-bromo-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

HRID 1008968

Reaction equation

HRID 1008968 reaction equation
[Br:1][C:2]1[N:6](C(OC(C)(C)C)=O)[C:5]2[CH:14]=[C:15]([C:17]([O:19][CH3:20])=[O:18])[S:16][C:4]=2[C:3]=1[CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.FC(F)(F)C(O)=O>C(Cl)Cl>[Br:1][C:2]1[NH:6][C:5]2[CH:14]=[C:15]([C:17]([O:19][CH3:20])=[O:18])[S:16][C:4]=2[C:3]=1[CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67298537methyl 5-bromo-4-(tert-butoxycarbonyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

Product 1

HCID 58679077methyl 5-bromo-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylateYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution (0.1 M) of methyl 5-bromo-4-(tert-butoxycarbonyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate (prepared as described in WO2005/023819) in CH2Cl2 was treated with trifluoroacetic acid (1:1). The reaction mixture was stirred at RT for 1 h. All volatiles were evaporated giving a residue that was purified by flash chromatography (PE:EtOAc, 7:3) giving the title compound (79%) as solid. 1H-NMR (400 MHz, DMSO-d6, 300 K, δ) 7.60 (s, 1H), 3.80 (s, 3H), 2.66-2.55 (m, 1H), 1.85-1.20 (m, 10H). MS (ES+) m/z: 342, 344 [M+H]+.

Workup

  1. customAll volatiles were evaporated
  2. customgiving a residue that
  3. customwas purified by flash chromatography (PE:EtOAc, 7:3)

Sources & evidence

ORD record
ord-512700941f8b40fbaea53662ce3bd7dd
Source dataset
uspto-grants-2011_07
Patent number
US07973026B2

Linked notes

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