Imidazole → HCID 86696728, compound

HRID 2365874Notes

Reaction equation

HRID 2365874 reaction equation
[CH3:1][C:2]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])[CH3:3].[OH:9][CH:10]([C:13]1[N:14]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11][OH:12].N1C=CN=C1>ClCCl>[Si:5]([O:12][CH2:11][CH:10]([C:13]1[N:14]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2)[OH:9])([C:2]([CH3:4])([CH3:3])[CH3:1])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 86696727HCID 86696727, compound

Product 1

HCID 86696728HCID 86696728, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

TBSCl (1.3 g, 8.9 mmol) in dichloromethane (20 mL) was added dropwise at 0° C. over 10 minutes to a solution of tert-butyl 2-(1,2-dihydroxyethyl)-1H-indole-1-carboxylate (2.0 g, 7.2 mmol) and imidazole (1.20 g, 17.4 mmol) in DCM (30 mL). After being stirred at room temperature for 1 hour, the mixture was washed with water (2×50 mL) and brine, dried, and concentrated. The residue was purified by silica gel column chromatography eluting with petroleum ether/ethyl acetate (50:1) to give an oil, which was further purified by prep-HPLC to afford tert-butyl 2-(2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl)-1H-indole-1-carboxylate (500 mg, 18% yield) as an oil. LCMS (ESI) m/z: 318.3 [M−56−17]+.

Workup

  1. washthe mixture was washed with water (2×50 mL) and brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography
  5. washeluting with petroleum ether/ethyl acetate (50:1)
  6. customto give an oil, which
  7. customwas further purified by prep-HPLC

Sources & evidence

ORD record
ord-856e00d25e9d4801b75d2321418aea62
Source dataset
uspto-grants-2014_04
Patent number
US08697715B2

Reaction notes

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