Imidazole → HCID 15307470, compound

HRID 1947023Notes

Reaction equation

HRID 1947023 reaction equation
[CH:1]([Si:4](Cl)([CH:8]([CH3:10])[CH3:9])[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].N1C=CN=C1.[NH:17]1[C:25]2[CH:24]=[CH:23][CH:22]=[C:21]([OH:26])[C:20]=2[CH:19]=[CH:18]1>>[CH:1]([Si:4]([CH:8]([CH3:10])[CH3:9])([CH:5]([CH3:7])[CH3:6])[O:26][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:20]=1[CH:19]=[CH:18][NH:17]2)([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 795ImidazoleHCID 754211H-indol-4-olHCID 139400Triisopropylsilyl chloride

Product 1

HCID 15307470HCID 15307470, compoundYield 80%

Procedure

Tri-isopropylsilyl chloride (TIPS-Cl, 15.86 mL) and imidazole (5.62 g) were added to 1H-indol-4-ol (10 g) in DMC (200 mL), and stirred at RT overnight. The resulting solid was filtered and washed with DCM. The filtrate was concentrated and purified on a column with 100% hexane to 25% EtOAc/hexane, and the fractions collected, concentrated, triturated with cold hexane, and the resulting solid was filtered and dried at 50° C. to yield 4-(triisopropylsilyl-oxy)-1H-indole (17 g, ˜80%).

Workup

  1. filtrationThe resulting solid was filtered
  2. washwashed with DCM
  3. concentrationThe filtrate was concentrated
  4. custompurified on a column with 100% hexane to 25% EtOAc/hexane
  5. customthe fractions collected
  6. concentrationconcentrated
  7. customtriturated with cold hexane
  8. filtrationthe resulting solid was filtered
  9. customdried at 50° C.

Sources & evidence

ORD record
ord-4fc5d1da5cd542d99d7ad71c2101f535
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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