ethyl (2E)-4-{[(4-iodo-1H-pyrrol-2-yl)carbonyl]amino}but-2-enoate → HCID 86658330, compound

HRID 874918Notes

Reaction equation

HRID 874918 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([C:7]([NH:9][CH2:10]/[CH:11]=[CH:12]/[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:8])[NH:5][CH:6]=1>C(#N)C>[I:1][C:2]1[CH:3]=[C:4]2[C:7](=[O:8])[NH:9][CH2:10][CH:11]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:5]2[CH:6]=1

Participants

3

Reactant 1

HCID 86658329ethyl (2E)-4-{[(4-iodo-1H-pyrrol-2-yl)carbonyl]amino}but-2-enoate

Product 1

HCID 86658330HCID 86658330, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Diaza(1,3)bicyclo[5.4.0]undecane (DBU) (0.04 mL, 0.3 mmol) was added to a solution of ethyl (2E)-4-{[(4-iodo-1H-pyrrol-2-yl)carbonyl]amino}but-2-enoate (X, where R1=OCH2CH3) (0.45 g, 1.3 mmol) in acetonitrile (8 mL) and the reaction mixture was stirred at room temperature for 30 min. The solvent was evaporated under vacuum and the residue purified by flash chromatography (SiO2, hexane-EtOAc 1:1) to obtain compound ethyl (7-iodo-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl)acetate (XII, where R1=OCH2CH3) as an off-white solid (0.35 g, 79% yield).

Workup

  1. customThe solvent was evaporated under vacuum
  2. customthe residue purified by flash chromatography (SiO2, hexane-EtOAc 1:1)

Sources & evidence

ORD record
ord-83334d615f2a444d87c4ffc3d1cd997a
Source dataset
uspto-grants-2015_03
Patent number
US08981092B2

Reaction notes

Loading…