Diisopropylamine → HCID 69221149, 화합물

HRID 1392231노트

반응식

HRID 1392231 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 69221149HCID 69221149, 화합물수율 70%

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

(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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-39702e1e515b4bdf902419d6b935d1b0
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07342030B2

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