Phenethyl bromide → 1-(3-fluorobenzyl)-4-phenethoxypyridin-2(1H)-one

HRID 1948258Notes

Reaction equation

HRID 1948258 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][N:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]1=[O:13].Br[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][N:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:8][C:7]1=[O:13]

Participants

4

Reactant 2

HCID 7666Phenethyl bromideHCID 54724162HCID 54724162, compound

Product 1

HCID 589669601-(3-fluorobenzyl)-4-phenethoxypyridin-2(1H)-oneYield 58%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

According to Scheme 13 Method A: The title compound was prepared from 1-(3-fluorobenzyl)-4-hydroxypyridin-2(1H)-one (1 eq, 0.23 mmol, 0.05 g, Example 19 Step 2) and 1-(2-bromoethyl)benzene (2 eq, 0.46 mmol, 0.06 mL) according to the procedure described for Example 1 Step 2. Microwave conditions: 180° C. for 900s in acetonitrile (2 mL). The crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 25 g SiO2) using CH2Cl2/AcOEt 80/20 and by recrystallization in pentane to afford 1-(3-fluorobenzyl)-4-phenethoxypyridin-2(1H)-one (0.13 mmol, 43 mg, 58%) as a white solid.

Workup

  1. custom180° C.
  2. customThe crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 25 g SiO2)
  3. customby recrystallization in pentane

Sources & evidence

ORD record
ord-c5eb82d3c8d84396b1f6f6f4c856f08b
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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