Sodium Sulfite → 1-[3-Fluoro-6-(methoxy)-1,5-naphthyridin-4-yl]-1,2-ethanediol

HRID 639022

Reaction equation

HRID 639022 reaction equation
C(C1[C:4]([F:15])=[CH:5][N:6]=[C:7]2[C:12]=1[N:11]=[C:10]([O:13][CH3:14])[CH:9]=[CH:8]2)=C.S([O-])([O-])=O.[Na+].[Na+].[C:22]([OH:26])(C)([CH3:24])[CH3:23].[OH2:27]>>[F:15][C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:23]=1[CH:22]([OH:26])[CH2:24][OH:27])=[N:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2

Participants

4

Reactant 3

HCID 24437Sodium SulfiteHCID 575995778-Ethenyl-7-fluoro-2-(methoxy)-1,5-naphthyridineHCID 714019492-Methylpropan-2-ol--water (1/1)

Product 1

HCID 671345911-[3-Fluoro-6-(methoxy)-1,5-naphthyridin-4-yl]-1,2-ethanediolYield 96%

Procedure

To a solution of AD-mixβ (50 g) in tert-butanol/water (200 mL/200 mL), cooled in an ice-bath for 30 minutes, 8-ethenyl-7-fluoro-2-(methyloxy)-1,5-naphthyridine (Preparation 6) (8 g, 39.2 mmol) was added and the reaction mixture was stirred at room temperature for 48 hours. Sodium sulfite (75 g) was added and the mixture was stirred for a further 30 minutes. It was extracted with diethyl ether then several times with 10% methanol in chloroform. The organic extract was evaporated under vacuum to afford the desired product as an oil (8.93 g, 96%). MS (+ve ion electrospray) m/z 239 (MH+); enantiomeric excess=44%, as determined by chiral analytical HPLC.

Workup

  1. stirringthe mixture was stirred for a further 30 minutes
  2. extractionIt was extracted with diethyl ether
  3. extractionThe organic extract
  4. customwas evaporated under vacuum

Sources & evidence

ORD record
ord-e503c4dd0dbb4ff59358036b82935dda
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Linked notes

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