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

HRID 1943621Notes

Reaction equation

HRID 1943621 reaction equation
FC(F)(F)C(O)=O.[NH2:8][CH2:9]/[CH:10]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13].ClC(Cl)(Cl)[C:19]([C:21]1[NH:22][CH:23]=[C:24]([I:26])[CH:25]=1)=[O:20].C(N(CC)C(C)C)(C)C>ClCCl>[I:26][C:24]1[CH:25]=[C:21]([C:19]([NH:8][CH2:9]/[CH:10]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:20])[NH:22][CH:23]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 116816022,2,2-trichloro-1-(4-iodo-1H-pyrrol-2-yl)ethan-1-oneHCID 72699081ethyl (2E)-4-aminobut-2-enoate trifluoroacetate

Product 1

HCID 86658329ethyl (2E)-4-{[(4-iodo-1H-pyrrol-2-yl)carbonyl]amino}but-2-enoateYield 68.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl (2E)-4-aminobut-2-enoate trifluoroacetate (IV) (0.97 g, 4 mmol) was added to a solution of 2,2,2-trichloro-1-(4-iodo-1H-pyrrol-2-yl)ethanone (IX) (0.68 g, 2 mmol) and N,N-diisopropylethylamine (DIPEA) (2.7 mL, 16 mmol) in dichloromethane (20 mL) and the reaction mixture was stirred at room temperature overnight. The solvent was evaporated under vacuum and the residue purified by flash chromatography (SiO2, hexane-EtOAc 1:1) to obtain compound ethyl (2E)-4-{[(4-iodo-1H-pyrrol-2-yl)carbonyl]amino}but-2-enoate (X, where R1=OCH2CH3) as an off-white solid (0.48 g, 68% 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-3c1ed7253d4649e1b73d640e6e74305b
Source dataset
uspto-grants-2013_03
Patent number
US08394802B2

Reaction notes

Loading…