Sodium Carbonate → 4-Ethoxycarbonyl-2-(4-fluoro-2-methylphenyl)pyridine

HRID 1436900노트

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HRID 1436900 반응식
Cl[C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][N:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C>[CH2:8]([O:7][C:5]([C:4]1[CH:10]=[CH:11][N:12]=[C:2]([C:15]2[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:14]=2[CH3:13])[CH:3]=1)=[O:6])[CH3:9]

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 2734665(4-Fluoro-2-methylphenyl)boronic acidHCID 2762942Ethyl 2-chloroisonicotinate

생성물 1

HCID 579394474-Ethoxycarbonyl-2-(4-fluoro-2-methylphenyl)pyridine수율 88.8%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 1140Toluene용매

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온도
60 °C

실험 절차

In a mixed solvent of 250 ml of toluene and 50 ml of ethanol were dissolved 20 g of ethyl 2-chloroisonicotinate and 20 g of 2-methyl-4-fluorophenylboronic acid, and 5.8 g of palladium tetrakistriphenylphosphine and 250 ml of a 2M aqueous sodium carbonate solution, and the mixture was stirred at 50 to 70° C. for 2 hours. The solution was cooled down to room temperature and extracted by adding ethyl acetate and water. The organic layer was further washed with water, and dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1), to give 24.8 g of 4-ethoxycarbonyl-2-(4-fluoro-2-methylphenyl)pyridine as shown in Table 132 below.

후처리

  1. temperatureThe solution was cooled down to room temperature
  2. extractionextracted
  3. additionby adding ethyl acetate and water
  4. washThe organic layer was further washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1)

출처 및 근거

ORD 기록
ord-1967ab9918e540eba3c5af63e6a7c767
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07619092B2

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