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

HRID 1522547노트

반응식

HRID 1522547 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a58b868b655f4f409c464457c1063e99
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073918B2

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