Diisopropylamine → HCID 69221149、化合物

HRID 1392231ノート

反応式

HRID 1392231 の反応式
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[CH:12][C:11](I)=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:16]([N:20]1[CH:24]=[CH:23][N:22]=[N:21]1)[CH2:17][C:18]#[CH:19].C(NC(C)C)(C)C.C(OCC)(=O)C>C1COCC1.[Cu](I)I>[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:19]#[C:18][CH2:17][CH2:16][N:20]2[CH:24]=[CH:23][N:22]=[N:21]2)=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 7912DiisopropylamineHCID 8857Ethyl AcetateHCID 17750156tert-Butyl (5-iodopyridin-2-yl)carbamateHCID 184535221-But-3-ynyl-1H-[1,2,3]triazole

生成物 1

HCID 69221149HCID 69221149、化合物収率 70%

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

(5-Iodo-pyridin-2-yl)-carbamic acid tert-butyl ester (3.45 g, 10.77 mmol) was dissolved in anhydrous THF (30 ml) under an argon atmosphere and treated with (PPh3)2Pd(II)Cl2 (0.6 g, 0.86 mmol) and copper iodide (0.2 g, 1.1 mmol). To this mixture a solution of 1-but-3-inyl-1H-[1,2,3]triazole (2.1 g, 17.24 mmol) in anhydrous THF (20 ml) is added dropwise at 0° C. followed by diisopropyl-amine (7.6 mL, 53.88 mmol). After stirring for 6 h at room temperature ethyl acetate (100 mL) was added, the mixture was washed with water, brine and dried over sodium sulfate. After removal of the solvents the crude product was purified by column chromatography on silica gel (dichloro methane/methanol 98:2) yielding [5-(4-[1,2,3]triazol-1-yl-but-1-ynyl)-pyridin-2-yl]-carbamic acid tert-butyl ester as light yellow solid (2.35 g, 70%).

後処理

  1. additionwas added
  2. washthe mixture was washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of the solvents the crude product
  5. customwas purified by column chromatography on silica gel (dichloro methane/methanol 98:2)

出典と根拠

ORDレコード
ord-39702e1e515b4bdf902419d6b935d1b0
出典データセット
uspto-grants-2008_03
特許番号
US07342030B2

反応ノート

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