Water → 6-(2,4-Difluorophenoxy)-2-formylnicotinonitrile

HRID 1620408노트

반응식

HRID 1620408 반응식
[F:1][C:2]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7](/[CH:13]=C/N(C)C)[N:6]=1.O.I([O-])(=O)(=O)=[O:25].[Na+]>C1COCC1>[F:1][C:2]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([CH:13]=[O:25])[N:6]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 23667635Sodium periodateHCID 86664562(E)-6-(2,4-Difluorophenoxy)-2-(2-(dimethylamino)vinyl)nicotinonitrile

생성물 1

HCID 848198116-(2,4-Difluorophenoxy)-2-formylnicotinonitrile

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

At RT, to the product of step 2 above in THF (70.00 mL) and water (70.00 mL) was added sodium periodate (8.9 g, 42 mmol) in one portion and the reaction mixture was allowed to stir at RT for 2 h, resulting in the formation of a yellow suspension. The suspension was passed through a flitted funnel, washing with THF (2×10 mL). The filtrate was concentrated under reduced pressure and the remaining mixture was extracted with DCM (2×30 mL). The organic layers were combined, dried over MgSO4, filtered and concentrated. Purification on the ISCO (40 g column, 20-60% EtOAc in hexanes) afforded 6-(2,4-difluorophenoxy)-2-formylnicotinonitrile as a light yellow crystalline solid. MS (ESI, pos.ion) m/z: M+1=261.0

후처리

  1. customresulting in the formation of a yellow suspension
  2. customThe suspension was passed through a flitted funnel
  3. washwashing with THF (2×10 mL)
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. extractionthe remaining mixture was extracted with DCM (2×30 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification on the ISCO (40 g column, 20-60% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-89bca07b03de484bbddf0e28ee5344bf
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772481B2

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