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

HRID 747785

Reaction equation

HRID 747785 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6](I)=[C:7]([CH:19]=1)[O:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])#[N:2].[C:21]([NH:24][C:25](=[CH2:30])[C:26]([O:28][CH3:29])=[O:27])(=[O:23])[CH3:22].C(N(CC)CC)C.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:21]([NH:24][C:25](=[CH:30][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:19][C:7]=1[O:8][CH2:9][CH2:10][NH:11][C:12]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:18])[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 6342AcetonitrileSolvent

Procedure

15.3 g (39.5 mmol) of t-butyl [2-(5-cyano-2-iodophenoxy)ethyl]carbamate, 9.05 g (63.2 mmol) of methyl 2-acetamidoacrylate, 11 ml (79 mmol) of triethylamine, 1.3 g of palladium (II) acetate and 7.30 g of tris(2-methylphenyl)phosphine were stirred in 150 ml of acetonitrile overnight. The solvent was distilled off, and the residue was treated by the silica gel chromatography (ethyl acetate/hexane) to obtain the crude product, which was washed with hexane and a mixed solvent of hexane/ethyl acetate, and then vacuum-dried to obtain the title compound.

Workup

  1. distillationThe solvent was distilled off
  2. additionthe residue was treated by the silica gel chromatography (ethyl acetate/hexane)
  3. customto obtain the crude product, which
  4. washwas washed with hexane
  5. dry with materiala mixed solvent of hexane/ethyl acetate, and then vacuum-dried

Sources & evidence

ORD record
ord-4d3f22301f424f46b99bb90b2470852c
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Linked notes

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