Imidazole → 5-{[2-(Tert-butyldimethylsilyloxy)ethyl]aminomethyl}-1-(tert-butoxycarbonyl)indole

HRID 20988Notes

Reaction equation

HRID 20988 reaction equation
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[OH:14][CH2:15][CH2:16][NH:17][CH2:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[N:24]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH:23]=[CH:22]2>CN(C=O)C>[Si:6]([O:14][CH2:15][CH2:16][NH:17][CH2:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[N:24]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH:23]=[CH:22]2)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 68492342HCID 68492342, compound

Product 1

HCID 684934765-{[2-(Tert-butyldimethylsilyloxy)ethyl]aminomethyl}-1-(tert-butoxycarbonyl)indoleYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a similar manner to Step 1 of Reference Example 18, 5-[(2-hydroxyethyl)aminomethyl]-1-(tert-butoxycarbonyl)indole (5.40 g) was dissolved in DMF (50 mL) and the solution was treated with imidazole (940 mg, 13.8 mmol) and tert-butyl dimethylsilylchloride (2.08 g, 13.8 mmol), followed by purification by slurry using diisopropyl ether and hexane to obtain 5-{[2-(tert-butyldimethylsilyloxy)ethyl]aminomethyl}-1-(tert-butoxycarbonyl)indole (4.80 g, yield 86%, 2 steps).

Workup

  1. customfollowed by purification by slurry

Sources & evidence

ORD record
ord-828e6addb0fe41f8b64fb2929a0e6766
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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