Imidazole → 5-(4-[2-(Tert-butyldimethylsilyloxy)ethyl]-1-piperazinylmethyl)-1-(tert-butoxycarbonyl)indole

HRID 20986Notes

Reaction equation

HRID 20986 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:15]=[CH:14]3)[CH2:6][CH2:5]1.N1C=CN=C1.[Si:32](Cl)([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33]>CN(C=O)C>[Si:32]([O:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:15]=[CH:14]3)[CH2:6][CH2:5]1)([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 68490755HCID 68490755, compound

Product 1

HCID 684908615-(4-[2-(Tert-butyldimethylsilyloxy)ethyl]-1-piperazinylmethyl)-1-(tert-butoxycarbonyl)indoleYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a similar manner to Step 1 of Reference Example 18, 5-[4-(2-hydroxyethyl)-1-piperazinylmethyl]-1-(tert-butoxycarbonyl)indole (5.02 g, 14.0 mmol) was dissolved in DMF (50 mL), and the solution was treated with imidazole (1.43 g, 21.0 mmol) and tert-butyldimethylsilyl chloride (3.16 g, 21.0 mmol) to obtain 5-(4-[2-(tert-butyldimethylsilyloxy)ethyl]-1-piperazinylmethyl)-1-(tert-butoxycarbonyl)indole (5.97 g, yield 90%).

Sources & evidence

ORD record
ord-d9f5bf04589944f49b120415ff708821
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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