Tetrahydrofuran → 2-Methyl-6-[(1-methylpiperidin-4-yl)-methyl]-3-nitropyridine

HRID 1892201

반응식

HRID 1892201 반응식
B1C2CCCC1CCC2.C1COCC1.[CH3:15][N:16]1[CH2:21][CH2:20][C:19](=[CH2:22])[CH2:18][CH2:17]1.C[C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[C:26]([CH3:33])[N:25]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:33][C:26]1[C:27]([N+:30]([O-:32])=[O:31])=[CH:28][CH:29]=[C:24]([CH2:22][CH:19]2[CH2:20][CH2:21][N:16]([CH3:15])[CH2:17][CH2:18]2)[N:25]=1

참가 물질

8

반응물 5

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 789669-Borabicyclo(3.3.1)nonaneHCID 849582,6-Dimethyl-3-nitropyridineHCID 139537Piperidine, 1-methyl,4-methylene-

생성물 1

HCID 584766172-Methyl-6-[(1-methylpiperidin-4-yl)-methyl]-3-nitropyridine수율 11.5%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 6228Dimethylformamide용매

반응 조건

온도
75 °C

실험 절차

To a solution of 9-BBN in THF (0.5 M, 4.93 mL, 2.46 mmol) was added 1-methyl-4-methylenepiperidine (274 mg, 2.46 mmol). The reaction mixture was allowed to stir at 75° C. for 1 h and was then allowed to cool to rt. The resulting solution was transferred into a solution of 2-methyl-5-nitro-6-methylpyridine (486 mg, 2.24 mmol) in DMF (11 mL). To the mixture were added [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) (1:1 complex with DCM, 54.9 mg, 0.0672 mmol) and potassium carbonate (402 mg, 2.91 mmol). The reaction mixture was allowed to stir for 3 h at rt. The mixture was quenched by the addition of water (10 mL). The aqueous solution was extracted with DCM. The organic solutions were combined, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 2-methyl-6-[(1-methylpiperidin-4-yl)-methyl]-3-nitropyridine (64 mg, 10%) as a white solid. LCMS (FAL): Rt=3.38 min, m/z=250.2 (M+H).

후처리

  1. temperatureto cool to rt
  2. stirringto stir for 3 h at rt
  3. customThe mixture was quenched by the addition of water (10 mL)
  4. extractionThe aqueous solution was extracted with DCM
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-d2cf6a676e91441b8fe3da07ecb80fa3
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507667B2

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