2,3-Butanediol → 2-(4-Formylphenyl)isonicotinonitrile

HRID 1531810노트

반응식

HRID 1531810 반응식
Br[C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=1.[F-].[Cs+].C[CH:13]([OH:17])[CH:14](O)[CH3:15]>C(OCC)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:13]([C:14]1[CH:15]=[CH:7][C:6]([C:2]2[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=2)=[CH:5][CH:4]=1)=[O:17]

참가 물질

6

반응물 3

HCID 2622,3-ButanediolHCID 25953Cesium fluorideHCID 117355442-Bromo-4-cyanopyridine

생성물 1

HCID 27638682-(4-Formylphenyl)isonicotinonitrile

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 3283Diethyl Ether용매

실험 절차

Benzaldehyde-4-boronic acid (1.36 g), 2-bromo-4-cyano pyridine (1.5 g), cesium fluoride (2.72 g) and tetrakis(triphenylphosphine)palladium(0) (285 mg) were mixed together in dimethyl ethylene glycol (30 ml ). The reaction mixture was refluxed for 16 hrs under a atmosphere of nitrogen after which time the cooled mixture was diluted with diethyl ether (40 ml ) and washed with water (40 ml), the organic layer was separated and washed with saturated brine, dried over MgSO4 and evaporated under reduced pressure. The crude product was purified by column chromatography eluting with Dichloromethane/Diethyl ether (97.5/2.5, v/v) to afford the title compound (0.81 g).

후처리

  1. temperatureThe reaction mixture was refluxed for 16 hrs under a atmosphere of nitrogen after which time the cooled mixture
  2. washwashed with water (40 ml)
  3. customthe organic layer was separated
  4. washwashed with saturated brine
  5. dry with materialdried over MgSO4
  6. customevaporated under reduced pressure
  7. customThe crude product was purified by column chromatography
  8. washeluting with Dichloromethane/Diethyl ether (97.5/2.5

출처 및 근거

ORD 기록
ord-4eaf23ffa284444e9eccd9d9668b9518
출처 데이터셋
uspto-grants-2001_03
특허 번호
US06200978B1

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