Triethylamine → Methyl 2-Acetamido-3-[2-(2-(t-butoxycarbonylamino)ethoxy)-4-cyanophenyl]acrylate

HRID 49920Notes

Reaction equation

HRID 49920 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1I)[C:15]#[N:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:21]([NH:24][C:25](=[CH2:30])[C:26]([O:28][CH3:29])=[O:27])(=[O:23])[CH3:22].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:21]([NH:24][C:25](=[CH:30][C:19]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][C:12]=1[O:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:26]([O:28][CH3:29])=[O:27])(=[O:23])[CH3:22]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 98644Methyl 2-acetamidoacrylateHCID 11111864t-Butyl [2-(5-cyano-2-iodophenoxy)ethyl]carbamate

Product 1

HCID 68833044Methyl 2-Acetamido-3-[2-(2-(t-butoxycarbonylamino)ethoxy)-4-cyanophenyl]acrylate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
115 °C

Procedure

18.0 g (46.4 mmol) of 3-[2-(t-butoxycarbonylamino)ethoxy]-4-iodobenzonitrile was dissolved in 200 ml of dimethylformamide (DMF). 13.3 g (92.8 mmol) of methyl 2-acetamidoacrylate, 2.82 g (9.28 mmol) of tris(2-methylphenyl)phosphine, 1.04 g (4.64 mmol) of palladium (II) acetate and 12.9 ml (92.8 mmol) of triethylamine were added to the obtained solution, and they were stirred at 115° C. for 4 hours. The solvent was evaporated to obtain the crude product, which was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. customThe solvent was evaporated
  2. customto obtain the crude product, which
  3. customwas purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-046281170f08469dba7a019a60a28e30
Source dataset
uspto-grants-2004_03
Patent number
US06710056B2

Reaction notes

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