Methyl 1H-indole-2-carboxylate → (3-triisopropylsilanyloxy-propyl)-1H-indole-2-carboxylic acid

HRID 1883150Notes

Reaction equation

HRID 1883150 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][Si:6]([CH:13]([CH3:15])[CH3:14])([CH:10]([CH3:12])[CH3:11])[CH:7]([CH3:9])[CH3:8].C[O:17][C:18]([C:20]1[NH:21][C:22]2[C:27]([CH:28]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19]>>[CH:7]([Si:6]([CH:13]([CH3:15])[CH3:14])([CH:10]([CH3:12])[CH3:11])[O:5][CH2:4][CH2:3][CH2:2][N:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:28]=[C:20]1[C:18]([OH:19])=[O:17])([CH3:9])[CH3:8]

Participants

3

Reactant 2

HCID 70992Methyl 1H-indole-2-carboxylateHCID 23510097(3-Bromopropoxy)tri(propan-2-yl)silane

Product 1

HCID 23510070(3-triisopropylsilanyloxy-propyl)-1H-indole-2-carboxylic acid

Procedure

(3-Bromo-propoxy)-triisopropyl-silane (prepared from the corresponding alcohol, Greene, T. W. Protective Groups in Organic Chemistry; John Wiley & Sons, Inc.: New York, 1991) was reacted with 1H-indole-2-carboxylic acid methyl ester using procedures similar to Example 11 to give 1-(3-triisopropylsilanyloxy-propyl)-1H-indole-2-carboxylic acid as a white solid.

Sources & evidence

ORD record
ord-c8318427dcd54eddb48f7149063fa024
Source dataset
uspto-grants-2004_07
Patent number
US06759428B2

Reaction notes

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