Sodium Carbonate → 3-Chloro-5-phenylpicolinonitrile

HRID 340227

反応式

HRID 340227 の反応式
[Cl:1][C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[C:6](Cl)[CH:7]=1.CC1(C)C(C)(C)OB([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.C(OCC)(=O)C.O>[Cl:1][C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[C:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:7]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 570673Phenylboronic acid pinacol esterHCID 27696993,5-Dichloro-2-cyanopyridine

生成物 1

HCID 668755223-Chloro-5-phenylpicolinonitrile

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 21863594Toluene ethanol溶媒

実験手順

A solution of 3,5-dichloropicolinonitrile (1.0 eq.), 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane (1.0 eq.), tetrakis(triphenyl-phosphine)palladium (5 mol %), and 2N aqueous sodium carbonate solution (3.4 eq.) in toluene/ethanol (2:1, 0.04 M) was stirred at 100° C. for 2 hours, then 80° C. for 4 hours. After cooling to ambient temperature, the reaction content was diluted with ethyl acetate and water. The two phases were separated, and the aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vacuo. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-80% ethyl acetate in hexane to give a white solid.

後処理

  1. customThe two phases were separated
  2. extractionthe aqueous layer was extracted twice with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated en vacuo
  6. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)
  7. customto give a white solid

出典と根拠

ORDレコード
ord-62e0b7d7a59f4a5aa69d5e0c58d390bf
出典データセット
uspto-grants-2014_11
特許番号
US08895577B2

関連ノート

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