Diisopropylethylamine → HCID 86615140, compound

HRID 599537Notes

Reaction equation

HRID 599537 reaction equation
C(N(C(C)C)CC)(C)C.[CH3:10][O:11][C:12]1[CH:13]=[C:14](/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27])[CH:15]=[CH:16][C:17]=1[N:18]1[CH:22]=[C:21]([CH3:23])[N:20]=[CH:19]1.[F:29][C:30]1[CH:39]=[CH:38][C:33]([C:34](=[O:37])[CH2:35]Br)=[CH:32][CH:31]=1.O.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[CH3:10][O:11][C:12]1[CH:13]=[C:14](/[CH:24]=[CH:25]/[C:26]([O:28][CH2:35][C:34]([C:33]2[CH:38]=[CH:39][C:30]([F:29])=[CH:31][CH:32]=2)=[O:37])=[O:27])[CH:15]=[CH:16][C:17]=1[N:18]1[CH:22]=[C:21]([CH3:23])[N:20]=[CH:19]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 59528030(E)-3-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]acrylic acidHCID 86585896Sodium bicarbonate water

Product 1

HCID 86615140HCID 86615140, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

IPEA (0.28 mL) was added to a solution of (E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylic acid (200 mg) and 4-fluorophenacyl bromide (185 mg) in DMF (3 mL), and the reaction solution was stirred at room temperature for one hour. Ethyl acetate and saturated sodium bicarbonate water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was suspended in diethyl ether, and the solid was collected by filtration to obtain 230 mg of the title compound. The property values of the compound are as follows.

Workup

  1. customthe organic layer was separated
  2. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-2c90fa0e1de44739b9cf0db1763f2332
Source dataset
uspto-grants-2011_03
Patent number
US07897632B2

Reaction notes

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