Toluene → 2-Methoxy-4,6-dimethyl-5-phenyl-nicotinonitrile

HRID 1818899노트

반응식

HRID 1818899 반응식
I[C:2]1[C:3]([CH3:13])=[N:4][C:5]([O:11][CH3:12])=[C:6]([C:9]=1[CH3:10])[C:7]#[N:8].[C:14]1(B(O)O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>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.C(O)C>[CH3:12][O:11][C:5]1[N:4]=[C:3]([CH3:13])[C:2]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:9]([CH3:10])[C:6]=1[C:7]#[N:8]

참가 물질

7

반응물 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 567775115-Iodo-2-methoxy-4,6-dimethylpyridine-3-carbonitrile

생성물 1

HCID 689006662-Methoxy-4,6-dimethyl-5-phenyl-nicotinonitrile수율 78.6%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매

실험 절차

5-iodo-2-methoxy-4,6-dimethyl-nicotinonitrile (1.6 g, 5.554 mmol), Pd(PPh3)4 (642 mg, 0.555 mmol), phenyl boronic acid (1.05 g, 8.331 mmol), and anhydrous potassium carbonate (1.54 g, 11.11 mmol) were suspended in the mixed solution of 60 mL of anhydrous toluene and 3 mL of anhydrous ethanol, and then heated to reflux for about 72 hours under the nitrogen atmosphere. The mixture was filtered, added with 100 mL of a saturated solution of ammonium chloride and then extracted twice with 100 mL of methylene chloride. The resulting organic layer was dried with anhydrous sodium sulfate, and then concentrated. A silica gel column chromatography (5% EtOAc/Hexanes) was performed on the resulting residue and 1.04 g (78%) of 2-methoxy-4,6-dimethyl-5-phenyl-nicotinonitrile was obtained in pale yellow solid.

후처리

  1. temperatureheated
  2. temperatureto reflux for about 72 hours under the nitrogen atmosphere
  3. filtrationThe mixture was filtered
  4. additionadded with 100 mL of a saturated solution of ammonium chloride
  5. extractionextracted twice with 100 mL of methylene chloride
  6. dry with materialThe resulting organic layer was dried with anhydrous sodium sulfate
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e295f9b626f64ef0bb89a218a305ebcd
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07601736B2

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