Diisopropylamine → HCID 69221149, compound

HRID 1392231Notes

Reaction equation

HRID 1392231 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 69221149HCID 69221149, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

(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%).

Workup

  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)

Sources & evidence

ORD record
ord-39702e1e515b4bdf902419d6b935d1b0
Source dataset
uspto-grants-2008_03
Patent number
US07342030B2

Reaction notes

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