Cesium carbonate → 6-Butyl-4-methoxycarbonyl-2-oxo-1-(2-fluoro-4-iodophenylmethyl)-1,2-dihydropyridine

HRID 343962Notes

Reaction equation

HRID 343962 reaction equation
[CH2:1]([C:5]1[NH:10][C:9](=[O:11])[CH:8]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH:6]=1)[CH2:2][CH2:3][CH3:4].[F:16][C:17]1[CH:24]=[C:23]([I:25])[CH:22]=[CH:21][C:18]=1[CH2:19]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC>[CH2:1]([C:5]1[N:10]([CH2:19][C:18]2[CH:21]=[CH:22][C:23]([I:25])=[CH:24][C:17]=2[F:16])[C:9](=[O:11])[CH:8]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 152251016-Butyl-4-methoxycarbonyl-2-oxo-1,2-dihydropyridineHCID 222404061-(Bromomethyl)-2-fluoro-4-iodobenzene

Product 1

HCID 545123986-Butyl-4-methoxycarbonyl-2-oxo-1-(2-fluoro-4-iodophenylmethyl)-1,2-dihydropyridine

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 2.09 g (10 mmol) of the compound from Example VIII, 3.14 g (10 mmol) of 2-fluoro-4-iodobenzyl bromide and 2.11 g (11 mmol) of caesium carbonate in 40 ml of DME is stirred at 20° C. under argon for 16 hours. The solvent is then removed in vacuo, the residue is taken up in methylene chloride/water, the aqueous phase is extracted once with methylene chloride and the combined organic phases are dried over sodium sulphate and concentrated. The residue is purified on silica gel using petroleum ether/ethyl acetate (5:1 and 3:1).

Workup

  1. customThe solvent is then removed in vacuo
  2. extractionthe aqueous phase is extracted once with methylene chloride
  3. dry with materialthe combined organic phases are dried over sodium sulphate
  4. concentrationconcentrated
  5. customThe residue is purified on silica gel

Sources & evidence

ORD record
ord-337221c9aadf4b9c9d9fe1ddf784f8b0
Source dataset
uspto-grants-1999_01
Patent number
US05863930

Reaction notes

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