Chloroacetone → HCID 58966902, compound

HRID 1948219Notes

Reaction equation

HRID 1948219 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)[CH:10]=[CH:9][C:8]2=[O:20])=[C:4]([F:23])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:31][C:32](=[O:34])[CH3:33]>C1COCC1>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:31][C:32](=[O:34])[CH3:33])=[CH:15][CH:14]=3)[CH:10]=[CH:9][C:8]2=[O:20])=[C:4]([F:23])[CH:3]=1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 69345556HCID 69345556, compound

Product 1

HCID 58966902HCID 58966902, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
110 °C

Procedure

According to Scheme 14 Method A: A suspension of 1-(4-chloro-2-fluorobenzyl)-5-(4-hydroxyphenyl)pyridin-2(1H)-one (1 eq, 0.61 mmol, 0.20 g, Example 20 Step 2), K2CO3 (10 eq, 6.10 mmol, 0.84 g) and chloroacetone (4 eq, 2.43 mmol, 0.20 mL) in THF (10 mL) was heated in a microwave at 110° C. during 30 min. After filtration and evaporation, the resulting crude oil was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 25 g SiO2) using CH2Cl2/AcOEt 80/20 then washed with Et2O and was dried to afford 1-(4-chloro-2-fluorobenzyl)-5-(4-(2-oxopropoxy)phenyl)pyridin-2(1H)-one (0.12 mmol, 46 mg, 20%) as a white solid.

Workup

  1. filtrationAfter filtration and evaporation
  2. customthe resulting crude oil was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 25 g SiO2)
  3. washthen washed with Et2O
  4. customwas dried

Sources & evidence

ORD record
ord-5459a01c202343d4af0ceb49251b2b85
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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