Potassium Carbonate → 4-[(4-fluorobenzyl)oxy]-1-{4-[(1E)-3-hydroxy-1-propen-1-yl]phenyl}pyridin-2(1H)-one

HRID 254409

Reaction equation

HRID 254409 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][NH:11][C:10](=[O:14])[CH:9]=2)=[CH:4][CH:3]=1.Br[C:18]1[CH:23]=[CH:22][C:21](/[CH:24]=[CH:25]/[CH2:26][OH:27])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].O.N>C(OCC)(=O)C.CN(C=O)C>[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][N:11]([C:18]3[CH:23]=[CH:22][C:21](/[CH:24]=[CH:25]/[CH2:26][OH:27])=[CH:20][CH:19]=3)[C:10](=[O:14])[CH:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11183465(2E)-3-(4-bromophenyl)prop-2-en-1-olHCID 12896473Azane;hydrateHCID 220499004-(4-Fluorobenzyloxy)-1h-pyridin-2-one

Product 1

HCID 668728494-[(4-fluorobenzyl)oxy]-1-{4-[(1E)-3-hydroxy-1-propen-1-yl]phenyl}pyridin-2(1H)-oneYield 50.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
155 °C

Procedure

A mixture of 4-[(4-fluorobenzyl)oxy]pyridin-2(1H)-one (1.10 g, 5.0 mmol), (2E)-3-(4-bromophenyl)-2-propen-1-ol (1.28 g, 6 mmol), cuprous iodide (476 mg, 3 mmol), potassium carbonate (829 mg, 6 mmol) and DMF (20 mL) was stirred overnight at 155° C. The reaction liquid was cooled to room temperature, then poured into ammonia water, and ethyl acetate was added for extraction. The organic layer was washed with water and saturated saline, and dried with anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure, followed by purification by flash column chromatography (KP-Sil, hexane:ethyl acetate=1:1 to 0:1) to obtain the entitled compound (881 mg).

Workup

  1. customThe reaction liquid
  2. temperaturewas cooled to room temperature
  3. additionwas added for extraction
  4. washThe organic layer was washed with water and saturated saline
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationThe solvent was concentrated under reduced pressure
  7. customfollowed by purification by flash column chromatography (KP-Sil, hexane:ethyl acetate=1:1 to 0:1)

Sources & evidence

ORD record
ord-d8bc3e29064449df8c43fa1906e3655b
Source dataset
uspto-grants-2011_01
Patent number
US07875633B2

Linked notes

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