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

HRID 1040425ノート

反応式

HRID 1040425 の反応式
[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

参加物

6

反応物 2

HCID 130236446-Methoxy-2-pyridinecarbonitrileHCID 178461630HCID 178461630、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 178460666HCID 178460666、化合物触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-1950563d887f4ddea8e40216adfeccc5
出典データセット
uspto-grants-2013_10
特許番号
US08552205B2

反応ノート

読み込み中…