Imidazole → HCID 131733871, compound

HRID 708878Notes

Reaction equation

HRID 708878 reaction equation
[CH:1]1([C@H:4]([OH:30])[CH2:5][O:6][C:7]2[C:25]([F:26])=[CH:24][C:23]([N+:27]([O-:29])=[O:28])=[CH:22][C:8]=2[CH2:9][N:10]([CH3:21])[C:11](=[O:20])[O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:3][CH2:2]1.[Si:31](Cl)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32].N1C=CN=C1>CN(C=O)C>[Si:31]([O:30][C@@H:4]([CH:1]1[CH2:3][CH2:2]1)[CH2:5][O:6][C:7]1[C:25]([F:26])=[CH:24][C:23]([N+:27]([O-:29])=[O:28])=[CH:22][C:8]=1[CH2:9][N:10]([CH3:21])[C:11](=[O:20])[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 118101229HCID 118101229, compound

Product 1

HCID 131733871HCID 131733871, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 21E (99 mg, 0.237 mmol) in DMF (3 mL), was added tert-butyldimethylsilyl chloride (178 mg, 1.183 mmol) and imidazole (81 mg, 1.183 mmol). The reaction mixture was stirred at rt for 60 h., then was quenched with water, extracted with EtOAc (2×). The organic layer was washed with brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography to give 21F (92 mg, 0.173 mmol, 73.0% yield). MS (ESI) m/z: 533.4 (M+H)+.

Workup

  1. customwas quenched with water
  2. extractionextracted with EtOAc (2×)
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-6d2f7e64dd13489ea29a04694cc672a2
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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