Potassium Carbonate → 2-Chloro-6-(3-methoxyphenyl)pyridine

HRID 71074

反応式

HRID 71074 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1.[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15](Cl)[N:14]=1.C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O.C(COC)OC>[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[N:14]=1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 169892,6-DichloropyridineHCID 2734370(3-Methoxyphenyl)boronic acid

生成物 1

HCID 594893042-Chloro-6-(3-methoxyphenyl)pyridine

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

A mixture of m-methoxy-phenylboronic acid (10 g, 65.8 mmol), 2,6-dichloropyridine (9.7 g, 65.8 mmol), potassium carbonate (27.3 g, 197.4 mmol), triphenylphosphine (2.07 g, 7.9 mmol), dimethoxyethane 250 mL and water 80 mL was prepared. Nitrogen was bubbled directly in the mixture for 20 minutes. Then palladium acetate was added (0.44 g, 2.0 mmol). Nitrogen was bubbled again in the mixture for another 10 minutes. The mixture was heated to reflux under nitrogen overnight. The reaction mixture was cooled to room temperature. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were dried over magnesium sulfate, filtered and evaporated. The mixture was purified by silica column with up to 10% ethyl acetate in hexanes to gain 6.5 g colorless oil (45%).

後処理

  1. customwas prepared
  2. customNitrogen was bubbled directly in the mixture for 20 minutes
  3. additionThen palladium acetate was added (0.44 g, 2.0 mmol)
  4. customNitrogen was bubbled again in the mixture for another 10 minutes
  5. temperatureThe mixture was heated
  6. temperatureto reflux under nitrogen overnight
  7. customThe organic layer was separated
  8. extractionthe aqueous layer was extracted with dichloromethane
  9. dry with materialThe combined organic layers were dried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated
  12. customThe mixture was purified by silica column with up to 10% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-14f5509b1a96459b987abe0328b41779
出典データセット
uspto-grants-2014_09
特許番号
US08822708B2

関連ノート

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