Imidazole → HCID 131727351, compound

HRID 1783960Notes

Reaction equation

HRID 1783960 reaction equation
[Br:1][C:2]1[CH:6]=[N:5][NH:4][C:3]=1CO.[Si:9](Cl)([C:12]([CH3:15])([CH3:14])[CH3:13])(C)C.N1C=CN=[CH:18]1.C([O:24][CH2:25][CH3:26])C>CN(C)C=O>[Br:1][C:2]1[CH:3]=[N:4][NH:5][C:6]=1[C:25]([CH3:26])([CH3:18])[O:24][SiH2:9][C:12]([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 28928tert-Butyldimethylsilyl chlorideHCID 55255237(4-Bromo-1H-pyrazol-3-yl)-methanol

Product 1

HCID 131727351HCID 131727351, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (4-bromo-2H-pyrazol-3-yl)-methanol (0.64 mg, 3.63 mmol), tert-butyldimethylsilyl chloride (0.82 g, 5.45 mmol) and imidazole (0.42 g, 6.18 mmol) in N,N-dimethylformamide (20 mL) is stirred at room temperature overnight. The reaction mixture is diluted with a 50:50 mixture diethyl ether:ethyl acetate and washed with water (3×). The organic layers are dried over MgSO4, filtered and concentrated. The residue is purified by silica gel column chromatography eluting with 80:20 petroleum ether:ethyl acetate to afford the title compound (1.035 g, 98%).

Workup

  1. washethyl acetate and washed with water (3×)
  2. dry with materialThe organic layers are dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is purified by silica gel column chromatography
  6. washeluting with 80:20 petroleum ether

Sources & evidence

ORD record
ord-0b97dc8358f6448f9d7204d6e5127b9c
Source dataset
uspto-grants-2009_03
Patent number
US07501411B2

Reaction notes

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