Trifluoroacetic acid → (Z)-5,6-dihydro-4-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-oxo-4H-thieno[2,3-b]pyrrole-2-carboxylic acid

HRID 1860260Notes

Reaction equation

HRID 1860260 reaction equation
[CH3:1][O:2][C:3]1[CH:7]=[CH:6][NH:5][C:4]=1/[CH:8]=[C:9]1/[C:10]2[CH:17]=[C:16]([C:18]([O:20]C(C)(C)C)=[O:19])[S:15][C:11]=2[NH:12][C:13]/1=[O:14].FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3]1[CH:7]=[CH:6][NH:5][C:4]=1/[CH:8]=[C:9]1/[C:10]2[CH:17]=[C:16]([C:18]([OH:20])=[O:19])[S:15][C:11]=2[NH:12][C:13]/1=[O:14]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86584527tert-butyl (Z)-5,6-dihydro-4-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-oxo-4H-thieno[2,3-b]pyrrole-2-carboxylate

Product 1

HCID 67551189(Z)-5,6-dihydro-4-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-oxo-4H-thieno[2,3-b]pyrrole-2-carboxylic acidYield 71.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl (Z)-5,6-dihydro-4-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-oxo-4H-thieno[2,3-b]pyrrole-2-carboxylate (0.5 g, 1.45 mmol) was dissolved in dichloromethane (8 ml), cooled to 0° C., treated with trifluoroacetic acid (2 ml) and stirred for 3 hours warming to room temperature. The reaction mixture was evaporated to dryness and triturated with diethyl ether to give 300 mg of (Z)-5,6-dihydro-4-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-oxo-4H-thieno[2,3-b]pyrrole-2-carboxylic acid as a red solid. MS(ES): m/e 291 [M+H].

Workup

  1. temperaturewarming to room temperature
  2. customThe reaction mixture was evaporated to dryness
  3. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-f873f8ae414a4b6e85c005dae0c8e363
Source dataset
uspto-grants-2003_03
Patent number
US06528653B2

Reaction notes

Loading…