1H-Pyrrole-2-carboxaldehyde, 3-methoxy- → tert-butyl (Z)-5,6-dihydro-4-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-oxo-4H-thieno[2,3-b]pyrrole-2-carboxylate

HRID 1860259Notes

Reaction equation

HRID 1860259 reaction equation
[O:1]=[C:2]1[NH:6][C:5]2[S:7][C:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:9][C:4]=2[CH2:3]1.[CH3:17][O:18][C:19]1[CH:23]=[CH:22][NH:21][C:20]=1[CH:24]=O>N1CCCCC1.CC(O)C>[CH3:17][O:18][C:19]1[CH:23]=[CH:22][NH:21][C:20]=1/[CH:24]=[C:3]1/[C:4]2[CH:9]=[C:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[S:7][C:5]=2[NH:6][C:2]/1=[O:1]

Participants

5

Reactant 2

HCID 112864661H-Pyrrole-2-carboxaldehyde, 3-methoxy-HCID 18626967tert-butyl 5-oxo-4H,5H,6H-thieno[2,3-b]pyrrole-2-carboxylate

Product 1

HCID 86584527tert-butyl (Z)-5,6-dihydro-4-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-oxo-4H-thieno[2,3-b]pyrrole-2-carboxylateYield 40.3%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8082PiperidineSolvent

Conditions

Temperature
75 °C

Procedure

tert-Butyl 5,6-dihydro-5-oxo-4H-thieno[2,3-b]pyrrole-2-carboxylate (915 mg, 3.8 mmol) was dissolved in a solution of 1% piperidine in 2-propanol (10 ml). 3-Methoxypyrrole-2-carboxaldehyde (3.8 mmol, 480 mg) was added in one portion and the mixture heated at 75° C. for 1 hour. The reaction mixture was poured into an ice/water mixture (15 ml) and the precipitated solid was collected by filtration and washed with water to give 530 mg of tert-butyl (Z)-5,6-dihydro-4-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-oxo-4H-thieno [2,3-b]pyrrole-2-carboxylate as a red solid. MS(ES): m/e 347 [M+H].

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-4575ea57ca05440290ea4584c4cdef47
Source dataset
uspto-grants-2003_03
Patent number
US06528653B2

Reaction notes

Loading…