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

HRID 1436900ノート

反応式

HRID 1436900 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 1140Toluene溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-1967ab9918e540eba3c5af63e6a7c767
出典データセット
uspto-grants-2009_11
特許番号
US07619092B2

反応ノート

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