Water → HCID 58966954, compound

HRID 1948259Notes

Reaction equation

HRID 1948259 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+].[CH3:30][O:31][C:32](Cl)=[O:33].O>C1COCC1>[C:32](=[O:33])([O:31][CH3:30])[O:19][C:16]1[CH:17]=[CH:18][C:13]([C:11]2[CH:10]=[CH:9][C:8](=[O:20])[N:7]([CH2:6][C:5]3[CH:21]=[CH:22][C:2]([Cl:1])=[CH:3][C:4]=3[F:23])[CH:12]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 11430Potassium CarbonateHCID 69345556HCID 69345556, compound

Product 1

HCID 58966954HCID 58966954, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

According to Scheme 14 Method B: 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 methylchloroformate (4 eq, 2.43 mmol, 0.19 mL) in THF (10 mL) was stirred overnight at room temperature. Water was added to the reaction mixture, then the aqueous phase was extracted with AcOEt. The organic phase was dried over MgSO4, filtered and evaporated. The resulting crude oil was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 109 SiO2) using CH2Cl2/AcOEt 90/10 then washed with Et2O and was dried to afford 4-(1-(4-chloro-2-fluorobenzyl)-6-oxo-1,6-dihydropyridin-3-yl)phenyl methyl carbonate (0.36 mmol, 139 mg, 59%) as a white solid.

Workup

  1. extractionthe aqueous phase was extracted with AcOEt
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe resulting crude oil was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 109 SiO2)
  6. washthen washed with Et2O
  7. customwas dried

Sources & evidence

ORD record
ord-0d56a6029175487780a12f3e1b1bc36c
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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