Potassium Bicarbonate → (+/-)-5,10-Dihydro-1-isopropoxy-9-methoxy-10-(2-trifluoromethylphenyl)-pyrido[4,3-b][1,6]naphthyridine

HRID 2413949Notes

Reaction equation

HRID 2413949 reaction equation
[CH:1]([O:4][C:5]1[C:18]2[CH:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]([F:28])([F:27])[F:26])[C:16]3[C:15](=[O:29])[NH:14][CH:13]=[CH:12][C:11]=3[NH:10][C:9]=2[CH:8]=[CH:7][N:6]=1)([CH3:3])[CH3:2].F[B-](F)(F)F.[CH3:35][O+](C)C.C(=O)([O-])O.[K+]>ClCCCl>[CH:1]([O:4][C:5]1[N:6]=[CH:7][CH:8]=[C:9]2[C:18]=1[CH:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]([F:28])([F:27])[F:26])[C:16]1[C:15]([O:29][CH3:35])=[N:14][CH:13]=[CH:12][C:11]=1[NH:10]2)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 516893Potassium BicarbonateHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 9801169(+/-)-1,2,5,10-Tetrahydro-9-isopropoxy-1-oxo-10-(2-trifluoromethylphenyl)-pyrido[4,3-b][1,6]naphthyridine

Product 1

HCID 14072014(+/-)-5,10-Dihydro-1-isopropoxy-9-methoxy-10-(2-trifluoromethylphenyl)-pyrido[4,3-b][1,6]naphthyridine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

7.5 g (18.7 mMole) (±)-1,2,5,10-tetrahydro-9-isopropoxy-1-oxo-10-(2-trifluoromethylphenyl)-pyrido[4,3-b][1,6]naphthyridine (see Example 2) and 5.0 g (34 mMole) trimethyloxonium tetrafluoroborate are stirred for 24 hours at ambient temperature in 200 ml 1,2-dichloroethane under an atmosphere of nitrogen. The reaction mixture is then shaken with a saturated aqueous solution of potassium hydrogen carbonate and the organic phase is separated off, washed with water and dried over anhydrous sodium sulphate. The residue obtained after evaporation in a vacuum is chromatographed on silica gel with toluene/ethyl acetate (3:1 v/v). The fraction with the Rf of 0.2 is isolated and recrystallized from n-hexane/diisopropyl ether. There is obtained (±)-5,10-dihydro-1-isopropoxy-9-methoxy-10-(2-trifluoromethylphenyl)-pyrido[4,3-b][1,6]naphthyridine in the form of colorless crystals; mp 183°-185° C.

Workup

  1. customthe organic phase is separated off
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulphate
  4. customThe residue obtained
  5. customafter evaporation in a vacuum
  6. customis chromatographed on silica gel with toluene/ethyl acetate (3:1 v/v)
  7. customThe fraction with the Rf of 0.2 is isolated
  8. customrecrystallized from n-hexane/diisopropyl ether

Sources & evidence

ORD record
ord-475cb2cbf8b048e9a01488f7625fc133
Source dataset
uspto-grants-1988_01
Patent number
US04720499

Reaction notes

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