Imidazole → 4-(2-Triisopropylsilanyloxy-ethylamino)-nicotinonitrile

HRID 2264914Notes

Reaction equation

HRID 2264914 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]1[C:10]([C:11]#[N:12])=[CH:9][N:8]=[CH:7][CH:6]=1.N1C=CN=C1.[CH:18]([Si:21](Cl)([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])([CH3:20])[CH3:19]>CN(C=O)C>[CH:18]([Si:21]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[O:1][CH2:2][CH2:3][NH:4][C:5]1[C:10]([C:11]#[N:12])=[CH:9][N:8]=[CH:7][CH:6]=1)([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 59596532HCID 59596532, compound

Product 1

HCID 595964584-(2-Triisopropylsilanyloxy-ethylamino)-nicotinonitrileYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(2-hydroxy-ethylamino)-nicotinonitrile (500 mg, 3.07 mmol) and imidazole (250 mg, 3.68 mmol) in DMF (15 mL) was added triisopropylsilyl chloride (0.723 mL, 3.37 mmol). The reaction mixture stirred at room temperature for 2 hours. The mixture was then partitioned between ethyl acetate and water, the organic layer isolated and washed with brine, dried (Na2SO4), filtered and concentrated. The resultant residue was purified by flash chromatography (Si-PPC, pentane:ether, gradient 50:50 to 30:70) to provide the title compound as a white solid (753 mg, 77%). LCMS (method B): RT=2.92 min, M+H+=320.

Workup

  1. customThe mixture was then partitioned between ethyl acetate and water
  2. customthe organic layer isolated
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resultant residue was purified by flash chromatography (Si-PPC, pentane:ether, gradient 50:50 to 30:70)

Sources & evidence

ORD record
ord-bb9d240a7c964ce4a65cce478075a9e2
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

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