6-Methoxy-2-pyridinecarbonitrile → 1-(6-Methoxypyridin-2-YL)cyclopropan-1-amine

HRID 1040425노트

반응식

HRID 1040425 반응식
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]#[N:10])[CH:6]=[CH:5][CH:4]=1.[CH3:11][CH2:12][Mg+].[Br-]>C1COCC1.O.CC(O[Ti](OC(C)C)(OC(C)C)OC(C)C)C>[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]2([NH2:10])[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=1

참가 물질

6

반응물 2

HCID 130236446-Methoxy-2-pyridinecarbonitrileHCID 178461630HCID 178461630, 화합물

생성물 1

HCID 584310411-(6-Methoxypyridin-2-YL)cyclopropan-1-amine수율 22%

시약·촉매·용매 3

HCID 178460666HCID 178460666, 화합물촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 6-methoxy-pyridine-2-carbonitrile (1.50 g, 11.2 mmol) in THF (75 mL) at room temperature was added Ti(OiPr)4 (7.21 mL, 24.6 mmol). EtMgBr (14.9 mL, 44.7 mmol) was added dropwise. and the clear brown solution became heterogeneous. The reaction mixture was stirred for 1 h at room temperature. The reaction was diluted with water (10 mL), extracted with EtOAc (3×25 mL) and dried with MgSO4. After filtration, the solvent was removed in vacuo. The residue was purified by reverse phase HPLC to afford 380 mg (22%) of 1-(6-methoxy-pyridin-2-yl)-cyclopropylamine, m/z 166.3 [M+1]+.

후처리

  1. extractionextracted with EtOAc (3×25 mL)
  2. dry with materialdried with MgSO4
  3. filtrationAfter filtration
  4. customthe solvent was removed in vacuo
  5. customThe residue was purified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-1950563d887f4ddea8e40216adfeccc5
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552205B2

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