Imidazole → HCID 68481527, compound

HRID 1513995Notes

Reaction equation

HRID 1513995 reaction equation
[OH:1][CH2:2][C:3]1[N:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[C:5]([Br:14])[CH:4]=1.N1C=CN=C1.[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>CN(C=O)C.CCOCC>[Si:20]([O:1][CH2:2][C:3]1[N:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[C:5]([Br:14])[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

6

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 59362664HCID 59362664, compound

Product 1

HCID 68481527HCID 68481527, compoundYield 125.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Predried ethyl 6-hydroxymethyl-4-bromopyridine-2-carboxylate (1.4 g, 5 4 mmol) and imidazole (1.1 g, 6.5 mmol) were dissolved in dry DMF (1.7 mL). TBDPS-chloride (1.78 g, 6.5 mmol) was added portionwise, and the reaction was allowed to proceed for 3 h at r.t. The reaction mixture was diluted with Et2O (50 mL) and washed with water and sat. NaHCO3. The organic phase was dried over Na2SO4 and evaporated to dryness. Purification on silica gel (petroleum ether, by 40-60° C./ethyl acetate 5:2) yielded 2.5 g (92%) of the title compound.

Workup

  1. washwashed with water and sat. NaHCO3
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated to dryness
  4. customPurification on silica gel (petroleum ether, by 40-60° C./ethyl acetate 5:2)

Sources & evidence

ORD record
ord-9036d8578aba49c08aed6e9849cbd18b
Source dataset
uspto-grants-2012_07
Patent number
US08221719B2

Reaction notes

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