1-Methylpiperazine → 1-(2-Chloropyridin-4-YL)-4-methylpiperazine

HRID 885950

반응식

HRID 885950 반응식
[Cl:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][N:3]=1.[CH3:9][N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.CC(P(C(C)(C)C)C1[CH-]C=CC=1)(C)C.CC(P(C(C)(C)C)C1[CH-]C=CC=1)(C)C.[Cl-].[Cl-].[Fe+2].[Pd+2]>[Cl:1][C:2]1[CH:7]=[C:6]([N:13]2[CH2:14][CH2:15][N:10]([CH3:9])[CH2:11][CH2:12]2)[CH:5]=[CH:4][N:3]=1

참가 물질

6

반응물 3

HCID 531671-MethylpiperazineHCID 15165112-Chloro-4-iodopyridineHCID 23676156Sodium t-butoxide

생성물 1

HCID 722188991-(2-Chloropyridin-4-YL)-4-methylpiperazine수율 77%

시약·촉매·용매 2

HCID 53384307Dichloro[1,1'-bis(di-tert-butylphosphino)ferrocene]palladium(II)촉매HCID 1140Toluene용매

반응 조건

온도
115 °C

실험 절차

To a mixture of 2-chloro-4-iodopyridine (300 mg, 1.24 mmol) in toluene (4 mL) was added 1-methylpiperazine (0.14 mL, 1.24 mmol), sodium tert-butoxide (239 mg, 2.44 mmol), [1,1′-bis(di-tert-butylphosphino)ferrocene]palladium(II) dichloride (30 mg, 10% wt) and the suspension was heated to 115° C. under microwave irradiation for 30 minutes. The resulting mixture was concentrated in vacuo and partitioned between DCM (50 mL) and water (50 mL). The organic phase was washed with brine (50 mL), dried (MgSO4), and evaporated in vacuo to give the title compound (200 mg, 77%) as a brown oil. LCMS (ES+) 212.0 (M+H)+, RT 1.78 minutes (70% purity) (Method 2).

후처리

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. custompartitioned between DCM (50 mL) and water (50 mL)
  3. washThe organic phase was washed with brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-36642310d6664144b76b5f68ff44f51e
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242116B2

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