Sodium Carbonate → 2-(5-Chloro-2-fluorophenyl)pyridin-4-amine

HRID 1522547ノート

反応式

HRID 1522547 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6](B(O)O)[CH:7]=1.Cl[C:13]1[CH:18]=[C:17]([NH2:19])[CH:16]=[CH:15][N:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([C:13]2[CH:18]=[C:17]([NH2:19])[CH:16]=[CH:15][N:14]=2)[CH:7]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 844322-Chloropyridin-4-amineHCID 3718925(5-Chloro-2-fluoro-phenyl)boronic acid

生成物 1

HCID 674696072-(5-Chloro-2-fluorophenyl)pyridin-4-amine収率 20%

試薬・触媒・溶媒 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 312751,4-Dioxane溶媒

実験手順

5-Chloro-2-fluorophenylboronic acid (2.7 g, 15.48 mmol), 2-chloropyridin-4-amine (1.531 g, 11.91 mmol), sodium carbonate (5.96 ml, 11.91 mmol), and bis(triphenylphosphine) palladium chloride (0.836 g, 1.191 mmol) were combined in dioxane (54 mL) and refluxed for 3 hours. The reaction was cooled, the solvent removed in vacuo and the reaction mixture partitioned between brine and EtOAc. The organic layer was separated, dried over MgSO4 filtered and purified using NH silica column chromatography and a gradient of 5-95% EtOAc in hexanes to afford the title compound as a white solid (522 mg; 20%). ESI-MS: m/z 223.1 (M+H).

後処理

  1. temperaturerefluxed for 3 hours
  2. temperatureThe reaction was cooled
  3. customthe solvent removed in vacuo
  4. customthe reaction mixture partitioned between brine and EtOAc
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. custompurified

出典と根拠

ORDレコード
ord-a58b868b655f4f409c464457c1063e99
出典データセット
uspto-grants-2015_07
特許番号
US09073918B2

反応ノート

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