5-Benzyloxyindole → HCID 67431066, compound

HRID 2273711Notes

Reaction equation

HRID 2273711 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2)C1C=CC=CC=1.[H-].[Na+].[CH:20]([Si:23](Cl)([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25])([CH3:22])[CH3:21]>O1CCCC1>[CH:20]([Si:23]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[N:14]1[C:15]2[C:11](=[CH:10][C:9]([OH:8])=[CH:17][CH:16]=2)[CH:12]=[CH:13]1)([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 146245-BenzyloxyindoleHCID 24758Sodium hydrideHCID 139400Triisopropylsilyl chloride

Product 1

HCID 67431066HCID 67431066, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Benzyloxy-indole (1.0 g) was treated with NaH (135 mg) and triisopropylsilyl chloride (1.0 g) in tetrahydrofuran for 1 hour, purified by flash chromatography (98/2 ethyl acetate/hexanes), then debenzylated in ethanol (35 mL) using Pearlman's catalyst (0.19 g) and a hydrogen balloon.

Workup

  1. custompurified by flash chromatography (98/2 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-ad8931e005f24e11b8d4666fae58900f
Source dataset
uspto-grants-2015_09
Patent number
US09125913B2

Reaction notes

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