Imidazole → HCID 69516971, compound

HRID 1373759Notes

Reaction equation

HRID 1373759 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N:9]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]1=[O:19].[Si:20](Cl)([C:33]([CH3:36])([CH3:35])[CH3:34])([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.N1C=CN=C1>CN(C=O)C>[Si:20]([O:8][C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:19])[CH:4]=1)([C:33]([CH3:36])([CH3:35])[CH3:34])([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 69633402HCID 69633402, compound

Product 1

HCID 69516971HCID 69516971, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 73B (5.31 g, 20.81 mmol), tert-butyldiphenylsilyl chloride (5.68 mL, 21.85 mmol), imidazole (2.83 g, 41.62 mmol) in anhydrous DMF (100 mL) was heated at 50° C. for 2 days. The solvent was removed via vacuum pump. THF (200 mL) was added. The mixture was ultrosonicated. The suspension was filtered. The solution was dried with silica gel powder (20 g). 20% ethyl acetate in hexanes (1 L) and 30% ethyl acetate in hexanes (1 L) were used to perform flash chromatography to give the title compound (7 g, 68%). MS (APCI) m/z 492.19 (M−H)−; 1H NMR (500 MHz, CDCl3) δ ppm 1.10 (s, 9H) 6.64 (dd, J=8.73, 2.81 Hz, 1 H) 6.78 (d, J=8.73 Hz, 1 H) 6.86 (d, J=2.81 Hz, 1 H) 7.34–7.45 (m, 6 H) 7.70–7.75 (m, 4 H) 7.78 (dd, J=5.46, 2.96 Hz, 2 H) 7.92 (dd, J=5.30, 3.12 Hz, 2 H).

Workup

  1. customThe solvent was removed via vacuum pump
  2. additionTHF (200 mL) was added
  3. filtrationThe suspension was filtered
  4. customThe solution was dried with silica gel powder (20 g)

Sources & evidence

ORD record
ord-d5bd765c05de486b8686bb8dc72f5c8a
Source dataset
uspto-grants-2007_01
Patent number
US07163939B2

Reaction notes

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