Water → HCID 10297597, compound

HRID 1609547Notes

Reaction equation

HRID 1609547 reaction equation
[CH:1]([C:4]1[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[C:7]([CH2:22][OH:23])=[C:6]([CH:24]([CH3:26])[CH3:25])[N:5]=1)([CH3:3])[CH3:2].[H-].[Na+].[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.O>CN(C)C=O>[CH2:29]([O:23][CH2:22][C:7]1[C:8]([C:15]2[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)=[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:4]([CH:1]([CH3:3])[CH3:2])=[N:5][C:6]=1[CH:24]([CH3:25])[CH3:26])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 10291957Ethyl 2,6-Diisopropyl-4-(4-fluorophenyl)-3-hydroxymethylpyridine-5-carboxylate

Product 1

HCID 10297597HCID 10297597, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

4.5 g (12.5 mmol) of the compound from Example 4 in 50 ml of dimethylformamide are added dropwise under nitrogen to a suspension of 414 mg (13.8 mmol) of 80% strength sodium hydride in 20 ml of dimethylformamide at 0° C. and the mixture is stirred for 30 minutes at the same temperature. Subsequently, 1.65 ml (13.8 mmol) of benzyl bromide in 20 ml of dimethylformamide are added dropwise and the mixture is stirred for a further 3 h at room temperature. The mixture is poured into 300 ml of water at 0° C. and extracted three times using 150 ml of ether each time. The combined organic phases are washed once with saturated sodium chloride solution, dried over magnesium sulphate and concentrated in vacuo. The residue is chromatographed on a column (100 g of silica gel 70-230 mesh, φ3.5 cm, using ethyl acetate/petroleum ether 1:10).

Workup

  1. stirringthe mixture is stirred for a further 3 h at room temperature
  2. extractionextracted three times
  3. washThe combined organic phases are washed once with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue is chromatographed on a column (100 g of silica gel 70-230 mesh, φ3.5 cm, using ethyl acetate/petroleum ether 1:10)

Sources & evidence

ORD record
ord-876f896b162546d9beec6560d662dd23
Source dataset
uspto-grants-1995_03
Patent number
US05401746

Reaction notes

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