Imidazole → HCID 178455513, compound

HRID 532897Notes

Reaction equation

HRID 532897 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][OH:7])[N:3]=[CH:2]1.N1C=CN=C1.[CH3:13][C:14]([Si:17](Cl)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:16])[CH3:15]>CN(C=O)C>[Si:17]([O:7][CH2:6][C:4]1[N:3]=[CH:2][NH:1][CH:5]=1)([C:14]([CH3:16])([CH3:15])[CH3:13])([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 178519868HCID 178519868, compound

Product 1

HCID 178455513HCID 178455513, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of (1H-imidazol-4-yl)methanol (14.6 g, 108 mmol) in DMF (100 mL) was treated with imidazole (22.16 g, 325 mmol) and TBDPSCl (29.8 g, 108 mmol) and the mixture was stirred and heated to 50° C. for 6 h. It was then allowed to cool to RT, poured onto H2O and extracted with DCM. The combined org. layers were dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (SiO2, DCM/MeOH 100:0 to 90:10) afforded the title compound (35.3 g). UPLC-MS: MS 337.2 (M+H+); UPLC rt 1.04 min.

Workup

  1. temperatureto cool to RT
  2. additionpoured onto H2O
  3. extractionextracted with DCM
  4. dry with materiallayers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography (SiO2, DCM/MeOH 100:0 to 90:10)

Sources & evidence

ORD record
ord-ae774b5a162a4c649c36581a41552c8c
Source dataset
uspto-grants-2014_10
Patent number
US08853203B2

Reaction notes

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