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

HRID 639022

반응식

HRID 639022 반응식
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

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e503c4dd0dbb4ff59358036b82935dda
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691850B2

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