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

HRID 1531810ノート

反応式

HRID 1531810 の反応式
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]

参加物

6

反応物 3

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

生成物 1

HCID 27638682-(4-Formylphenyl)isonicotinonitrile

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 3283Diethyl Ether溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4eaf23ffa284444e9eccd9d9668b9518
出典データセット
uspto-grants-2001_03
特許番号
US06200978B1

反応ノート

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