Imidazole → HCID 66956091, compound

HRID 2066644Notes

Reaction equation

HRID 2066644 reaction equation
[CH:1]([Si:4](Cl)([CH:8]([CH3:10])[CH3:9])[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[Br:12][C:13]1[N:14]([CH2:21][CH2:22][CH:23]([OH:26])[CH2:24][OH:25])[CH:15]=[C:16]([N+:18]([O-:20])=[O:19])[N:17]=1.N1C=CN=C1>CN(C=O)C>[Br:12][C:13]1[N:14]([CH2:21][CH2:22][CH:23]([OH:26])[CH2:24][O:25][Si:4]([CH:8]([CH3:10])[CH3:9])([CH:5]([CH3:7])[CH3:6])[CH:1]([CH3:3])[CH3:2])[CH:15]=[C:16]([N+:18]([O-:20])=[O:19])[N:17]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 66956441HCID 66956441, compound

Product 1

HCID 66956091HCID 66956091, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triisopropylsilyl chloride (2.50 mL, 11.7 mmol) was added to a solution of diol 131 (3.11 g, 11.1 mmol) and imidazole (1.66 g, 24.4 mmol) in anhydrous DMF (30 mL) under N2 and then the mixture was stirred at room temperature for 18 h. The resulting mixture was added to ice-water (200 mL) and extracted with EtOAc (4×200 mL). The extracts were washed with water (200 mL) and then evaporated to dryness and the residue was chromatographed on silica gel. Elution with 0-20% EtOAc/petroleum ether firstly gave foreruns, and then further elution with 20-33% EtOAc/petroleum ether gave 4-(2-bromo-4-nitro-1H-imidazol-1-yl)-1-[(triisopropylsilyl)oxy]-2-butanol (132) (4.60 g, 95%) as a white solid: mp (CH2Cl2/pentane) 90-91° C.; 1H NMR (CDCl3) δ 7.89 (s, 1H), 4.24 (dd, J=7.7, 6.2 Hz, 2H), 3.74 (dd, J=9.6, 3.5 Hz, 1H), 3.62 (m, 1H), 3.53 (dd, J=9.6, 6.8 Hz, 1H), 2.59 (d, J=3.8 Hz, 1H), 1.95-1.82 (m, 2H), 1.17-1.03 (m, 21H). Anal. (C16H30BrN3O4Si) C, H, N.

Workup

  1. extractionextracted with EtOAc (4×200 mL)
  2. washThe extracts were washed with water (200 mL)
  3. customevaporated to dryness
  4. customthe residue was chromatographed on silica gel
  5. washElution with 0-20% EtOAc/petroleum ether firstly gave foreruns
  6. washfurther elution with 20-33% EtOAc/petroleum ether

Sources & evidence

ORD record
ord-9adf64860ccd4265b4c965b74677e3a1
Source dataset
uspto-grants-2012_10
Patent number
US08293734B2

Reaction notes

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