Imidazole → HCID 59226529, compound

HRID 2046865Notes

Reaction equation

HRID 2046865 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:15]([O:17][CH3:18])=[O:16])=[N:6][C:7]=1[CH:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1.N1C=CN=C1.[CH3:24][C:25]([Si:28](Cl)([CH3:30])[CH3:29])([CH3:27])[CH3:26].C(OCC)(=O)C>CN(C=O)C>[Si:28]([O:14][CH:11]1[CH2:10][CH2:9][CH:8]([C:7]2[N:6]=[C:5]([C:15]([O:17][CH3:18])=[O:16])[CH:4]=[CH:3][C:2]=2[F:1])[CH2:13][CH2:12]1)([C:25]([CH3:27])([CH3:26])[CH3:24])([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 59226500HCID 59226500, compound

Product 1

HCID 59226529HCID 59226529, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 5-fluoro-6-(4-hydroxycyclohexyl)picolinate (1.0 equiv.) in DMF (0.15 M) was added imidazole (4.0 equiv.) and TBDMSCl (2.5 equiv.). The reaction mixture was stirred at room temperature for 2 days, then added to ethyl acetate, washed with water, brine, dried over magnesium sulfate, filtered and concentrated to give methyl 6-(4-(tert-butyldimethylsilyloxy)cyclohexyl)-5-fluoropicolinate in 97% yield as a mixture of isomers (3:1). LC/MS=368.3 (M+H), Rt=1.4 and 1.42 min.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9aee410620f6457589a98053da85b40d
Source dataset
uspto-grants-2013_11
Patent number
US08592455B2

Reaction notes

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