Sodium Carbonate → 5-(4-Chlorophenyl)pyridin-2-amine

HRID 271643

反応式

HRID 271643 の反応式
C([O-])([O-])=O.[Na+].[Na+].[NH2:7][C:8]1[CH:13]=[CH:12][C:11](Br)=[CH:10][N:9]=1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19](OB(O)O)=[CH:18][CH:17]=1>O1CCOCC1.CO.CCOC(C)=O.O>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:11]2[CH:12]=[CH:13][C:8]([NH2:7])=[N:9][CH:10]=2)=[CH:18][CH:17]=1

参加物

8

反応物 3

HCID 10340Sodium CarbonateHCID 706222-Amino-5-bromopyridineHCID 17810664p-Chlorophenylboric acid

生成物 1

HCID 132426445-(4-Chlorophenyl)pyridin-2-amine

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

300 mL (600 mmol) of a 2 M Na2CO3 solution and 3.45 g (3.0 mmol) tetrakis-triphenylphosphane-palladium are added successively to a solution of 53.5 g (300 mmol) 2-amino-5-bromopyridine and 50.0 g (313 mmol) 4-chlorophenylboric acid in 1.0 L 1,4-dioxane and 250 mL methanol under argon. The reaction mixture is stirred for 2.5 h at 110° C. The solvent is eliminated i.vac., the residue is taken up in EtOAc and water. The organic phase is dried over Na2SO4 and the solvent is eliminated i.vac. Further purification is carried out by column chromatography on silica gel (gradient: DCM to DCM/MeOH 20:1).

後処理

  1. dry with materialThe organic phase is dried over Na2SO4
  2. customFurther purification

出典と根拠

ORDレコード
ord-80e0d4f23fad482f85ed42d47a9067e4
出典データセット
uspto-grants-2008_11
特許番号
US07452911B2

関連ノート

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