Potassium Carbonate → 2-Cyclopropyl-4-(trifluoromethyl)pyridine

HRID 1880728ノート

反応式

HRID 1880728 の反応式
Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][N:3]=1.B([O-])([O-])O[CH:14]1[CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1(C)C=CC=CC=1>[CH:14]1([C:2]2[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][N:3]=2)[CH2:16][CH2:15]1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 1449582-Chloro-4-(trifluoromethyl)pyridineHCID 86647340HCID 86647340、化合物

生成物 1

HCID 595703072-Cyclopropyl-4-(trifluoromethyl)pyridine収率 53.4%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

To 21 ml of toluene were added 1.9 g of 2-chloro-4-trifluoromethylpyridine, 1 g of cyclopropyl borate, 2.92 g of potassium carbonate and 0.26 g of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) dichloromethane complex (1:1), and the mixture was stirred at 100° C. for 10 hours. After allowing to cool, the reaction solution was poured into an aqueous saturated ammonium chloride solution, and the resultant solution was extracted with diethyl ether three times, washed with an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 1 g of 2-cyclopropyl-4-trifluoromethylpyridine.

後処理

  1. temperatureto cool
  2. extractionthe resultant solution was extracted with diethyl ether three times
  3. washwashed with an aqueous saturated sodium chloride solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-e4c54c416b7243aa8265405246bf6748
出典データセット
uspto-grants-2012_11
特許番号
US08318776B2

反応ノート

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