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

HRID 1860257Notes

Reaction equation

HRID 1860257 reaction equation
[O:1]=[C:2]1[NH:6][C:5]2[S:7][C:8]([C:10]([O:12]C(C)(C)C)=[O:11])=[CH:9][C:4]=2/[C:3]/1=[CH:17]/[C:18]1[NH:19][CH:20]=[CH:21][CH:22]=1.FC(F)(F)C(O)=O>ClCCl>[O:1]=[C:2]1[NH:6][C:5]2[S:7][C:8]([C:10]([OH:12])=[O:11])=[CH:9][C:4]=2/[C:3]/1=[CH:17]/[C:18]1[NH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86584525tert-butyl (Z)-5,6-dihydro-5-oxo-4-[(1H-pyrrol-2-yl)methylene]-4H-thieno[2,3-b]pyrrole-2-carboxylate

Product 1

HCID 69844590(Z)-5,6-dihydro-5-oxo-4-[(1H-pyrrol-2-yl)methylene]-4H-thieno[2,3-b]pyrrole-2-carboxylic acidYield 57.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl (Z)-5,6-dihydro-5-oxo-4-[(1H-pyrrol-2-yl)methylene]-4H-thieno[2,3-b]pyrrole-2-carboxylate (150 mg, 0.47 mmol) was dissolved in dichloromethane (8 ml), cooled to 0° C., treated with trifluoroacetic acid (0.75 ml) and stirred for 2 hours warming to room temperature. The reaction mixture was evaporated to dryness and triturated with diethyl ether to give 70 mg of (Z)-5,6-dihydro-5-oxo-4-[(1H-pyrrol-2-yl)methylene]-4H-thieno[2,3-b]pyrrole-2-carboxylic acid as a red solid. MS(ES): m/e 260 [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-da24d687946643daaec84715c6d43492
Source dataset
uspto-grants-2003_03
Patent number
US06528653B2

Reaction notes

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