Water → N-{4-[2-cyano-1-(3-ethoxy-4-methoxy-phenyl)-vinyl]-phenyl}acetamide

HRID 2378219Notes

Reaction equation

HRID 2378219 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][C:14]#[N:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2].I[C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:26])[CH3:25])=[CH:19][CH:18]=1.C([O-])(O)=O.[Na+].O>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:14]([CH:13]=[C:12]([C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:26])[CH3:25])=[CH:19][CH:18]=1)[C:6]1[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=1)#[N:15]

Participants

8

Reactant 4

HCID 962WaterHCID 12147N-(4-Iodophenyl)acetamideHCID 516892Sodium BicarbonateHCID 692055743-(3-Ethoxy-4-methoxy-phenyl)-acrylonitrile

Product 1

HCID 69202522N-{4-[2-cyano-1-(3-ethoxy-4-methoxy-phenyl)-vinyl]-phenyl}acetamideYield 37.2%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-(3-ethoxy-4-methoxy-phenyl)-acrylonitrile (0.7 g, 3.2 mmol), N-(4-iodo-phenyl)-acetamide (1.4 g, 5.4 mmol), NaHCO3 (1.1 g, 12.8 mmol), Bu4NBr (1.2 g, 3.6 mmol) and Pd(OAc)2 (0.04 g, 0.2 mmol) in DMF (15 mL) was heated at 70° C. for 2 days. The cooled mixture was poured into water (150 mL) and was extracted with EtOAc (3×50 mL). The combined organic extracts were washed with water (2×50 mL), brine (50 mL) and dried (MgSO4). Solvent was removed and the residue was purified by flash chromatography (silica gel, CH2Cl2:EtOAc 9:1) to afford N-{4-[2-cyano-1-(3-ethoxy-4-methoxy-phenyl)-vinyl]-phenyl}acetamide (0.4 g, 32%): mp 175-177° C.; 1H NMR (CDCl3) δ 7.51(d, J=8 Hz, 2H), 7.41 (s, 1H), 7.26 (d, J=9.0 Hz, 2H), 7.02-6.89 (m, 3H), 5.57 (s, 1H), 4.11-4.03 (q, J=7 Hz, 2H), 3.92 (s, 3H), 2.19 (s, 3H), 1.44 (t, J=7 Hz, 3H); 13C NMR (CDCl3) δ 168.38, 162.14, 150.93, 147.96, 139.91, 134.84, 129.58, 129.30, 123.08, 119.34, 118.53, 114.06, 111.01, 92.49, 64.53, 55.96, 24.65, 14.66; Anal Calcd for C20H20N2O3: C, 71.46; H, 5.99; N, 8.33. Found: C, 71.46, 6.01; N, 8.25.

Workup

  1. extractionwas extracted with EtOAc (3×50 mL)
  2. washThe combined organic extracts were washed with water (2×50 mL), brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. customSolvent was removed
  5. customthe residue was purified by flash chromatography (silica gel, CH2Cl2:EtOAc 9:1)

Sources & evidence

ORD record
ord-475075d697334409bfa6bdde11f47a06
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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