Cesium carbonate → (E)-3-(3-(2-(4,5-dihydro-1H-imidazol-2-yl)pyridin-4-yloxy)phenyl)-N-(3-isopropylphenyl)acrylamide

HRID 1994153Notes

Reaction equation

HRID 1994153 reaction equation
[OH:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]([CH3:21])[CH3:20])[CH:14]=2)=[O:11])[CH:5]=[CH:6][CH:7]=1.Cl[C:23]1[CH:28]=[CH:27][N:26]=[C:25]([C:29]2[NH:30][CH2:31][CH2:32][N:33]=2)[CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[NH:30]1[CH2:31][CH2:32][N:33]=[C:29]1[C:25]1[CH:24]=[C:23]([O:1][C:2]2[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]([CH3:21])[CH3:20])[CH:14]=3)=[O:11])[CH:5]=[CH:6][CH:7]=2)[CH:28]=[CH:27][N:26]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 58674642(E)-3-(3-hydroxyphenyl)-N-(3-isopropylphenyl)acrylamideHCID 591349594-chloro-2-(4,5-dihydro-1H-imidazol-2-yl)pyridine

Product 1

HCID 11661842(E)-3-(3-(2-(4,5-dihydro-1H-imidazol-2-yl)pyridin-4-yloxy)phenyl)-N-(3-isopropylphenyl)acrylamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (E)-3-(3-hydroxyphenyl)-N-(3-isopropylphenyl)acrylamide (3.20 mmol) in DMF (40 mL) was added 4-chloro-2-(4,5-dihydro-1H-imidazol-2-yl)pyridine (11.2 mmol) and cesium carbonate (16.0 mmol). The heterogeneous mixture was heated at 100° C. for 18 h and then cooled to rt. The mixture was diluted with water and extracted with EtOAc. The combined organic solutions were washed with water and brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography (90:10:1 DCM:MeOH:NH4OH) to give B-2. 1H NMR (300 MHz, d6-DMSO): δ 10.13 (s, 1H), 8.52 (d, J=5.6 Hz, 1H), 7.56-7.61 (m, 3H), 7.50-7.54 (m, 2H), 7.44-7.47 (m, 1H), 7.41 (d, J=2.8 Hz, 1H), 7.20-7.29 (m, 2H), 7.17 (dd, J=6.8, 2.8 Hz, 1H), 6.93-6.99 (m, 2H), 6.85 (d, J=15.6 Hz, 1H), 3.32 (s, 4H), 2.85 (sept, J=6.8 Hz, 1H), and 1.18 (d, J=7.2 Hz, 6H).

Workup

  1. temperaturecooled to rt
  2. extractionextracted with EtOAc
  3. washThe combined organic solutions were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (90:10:1 DCM:MeOH:NH4OH)
  8. customto give B-2

Sources & evidence

ORD record
ord-65055223b1ba457a816f4aaf9c08091c
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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