2-Amino-3-bromopyridine → 3-(5-Chloro-2-methoxyphenyl)pyridin-2-amine

HRID 1514011ノート

反応式

HRID 1514011 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6](B(O)O)[CH:7]=1.[NH2:13][C:14]1[C:19](Br)=[CH:18][CH:17]=[CH:16][N:15]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([C:19]2[C:14]([NH2:13])=[N:15][CH:16]=[CH:17][CH:18]=2)[CH:7]=1

参加物

7

反応物 2

HCID 8177002-Amino-3-bromopyridineHCID 27357515-Chloro-2-methoxyphenylboronic acid

生成物 1

HCID 640879063-(5-Chloro-2-methoxyphenyl)pyridin-2-amine収率 64.6%

試薬・触媒・溶媒 4

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl触媒HCID 22031701Potassium phosphate, tribasic, monohydrate触媒HCID 1140Toluene溶媒

実験手順

The 300 mL round bottom flask, equipped with magnetic stirrer and refluxed condenser, was charged with 5-chloro-2-methoxyphenylboronic acid (5.00 g, 33 mmol), 2-amino-3-bromopyridine (5.70 g, 33 mmol), Pd2(dba)3 (604 mg, 2 mol %), 2-dicylohexylphosphino-2′,6′-dimethoxybiphenyl (542 mg, 4 mol %), potassium phosphate tribasic monohydrate (22.8 mg, 3 eq) and 100 mL of toluene. The flask was filled with nitrogen, and the reaction mixture was heated to reflux and stirred under nitrogen atmosphere for 24 hours. Then reaction was cooled down to room temperature, filtered through silica plug and evaporated. The residue was subjected to column chromatography on silica gel, eluent hexane/ethyl acetate mixture 1:1, providing 5.0 g of 3-(5-chloro-2-methoxyphenyl)pyridin-2-amine as yellow solid. The structure was confirmed by NMR and MS spectroscopy.

後処理

  1. customThe 300 mL round bottom flask, equipped with magnetic stirrer
  2. temperaturerefluxed condenser
  3. additionThe flask was filled with nitrogen
  4. temperaturethe reaction mixture was heated
  5. temperatureto reflux
  6. customThen reaction
  7. filtrationfiltered through silica plug
  8. customevaporated

出典と根拠

ORDレコード
ord-fd4b0e6b5b8c4d9fa056d7493dcb4591
出典データセット
uspto-grants-2012_07
特許番号
US08221905B2

反応ノート

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