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Benzyl Bromide → 2-(Benzyloxy)-6-(4-chlorophenyl)-5-phenylnicotinonitrile

HRID 916926
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HRID 916926 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:13][C:12](=[O:14])[C:11]([C:15]#[N:16])=[CH:10][C:9]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:4][CH:3]=1.[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[CH2:23]([O:14][C:12]1[C:11]([C:15]#[N:16])=[CH:10][C:9]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[N:13]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 694176906-(4-Chlorophenyl)-5-(phenyl)-2-oxo-1,2-dihydropyridine-3-nitrile

생성물 1

HCID 101942452-(Benzyloxy)-6-(4-chlorophenyl)-5-phenylnicotinonitrile

시약·촉매·용매 2

HCID 962Water용매HCID 6228
Dimethylformamide
용매

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온도
55 °C

실험 절차

To a solution of 6-(4-chlorophenyl)-5-(phenyl)-2-oxo-1,2-dihydropyridine-3-nitrile (200 mg, 0.65 mmol) from Example 1, Step B in DMF (3 mL) was added benzyl bromide (0.10 mL, 0.85 mmol) and then cesium carbonate (276 mg, 0.85 mmol). The reaction was stirred at 55° C. for 3 h and was then diluted with water and extracted twice with methylene chloride. The organic layers were washed with a portion of brine and the combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. The products were separated by preparative TLC (30% ethyl acetate in hexanes) to give the desired higher Rf O-alkylation title product.

후처리

  1. extractionextracted twice with methylene chloride
  2. washThe organic layers were washed with a portion of brine
  3. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe products were separated by preparative TLC (30% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-bea225fb8e3a4a01beeae5c2d38ec55f
출처 데이터셋
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07271266B2

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